Swipe Right For Loneliness












[Swipe Right
for Loneliness]


S.D. Gately















Text copyright © 2017 S.D. Gately

All Rights Reserved
















To all the women who were sweet to me. I’m sorry.


Table of Contents


Chapter One

Part One: Your Real-life Profile

Part Two: A Beginners Guide to Dating on the Swipe-apps

Chapter Two

Part One: The First Date

Part Two: On Matching, Messaging, and Meeting Up

Chapter Three

Part One: Getting to Know Her

Part Two: The Women of the Swipe-apps

Chapter Four

Part One: Sex

Part Two: A Sex Rampage of Epic Proportions, Brought to You by Modern Technology

Chapter Five

Part One: Love

Part Two: Is Love Possible on the Swipe-apps?

Chapter Six

Part One: Reconciliation

Part Two: Atonement




In his 1854 book Walden, Henry David Thoreau said ‘The mass of men lead lives of quiet desperation,’ and I have no idea what he meant by that, because I never actually read Walden and I don’t feel like googling it. But ‘desperation’ probably refers to a man’s desperation to get laid, and ‘quiet’ refers to a man’s inability to speak when a pretty woman approaches him. The merest scent of an attractive female will turn the brains of most men to mush, and if Thoreau were alive today, he’d probably be scrolling through Instagram every night before bed to look at pictures of twenty-somethings in bikinis.

The wondrous beauty of the female form is something to behold – the fake eyelashes, long, primped hair, short skirts over toned, sexy legs, push-up bras that proudly display youthful tits, bare midriffs, belly button rings, back dimples – it’s overwhelming for the male brain to process. Even the stodgiest intellectual who claims to be above such base interests will gawk, albeit briefly, at some hot young nymph that catches his attention. Last week I caught some old codger walking hand-in-hand with his matronly wife at the Saturday Farmer’s Market. She’d once been a head-turner, you could tell, but time and age had left her to negotiate between her sagging tits and varicose vein-mottled legs. They passed by a hot college co-ed with a group of her friends, and from the look on his face, I could tell the old bastard fought the urge to cast a glance her way. I could see the mental battle in his head as he tried to remind himself that his wife, with her gray hair like fuse wire and bulbous, sagging tits, was the one he had promised to be with forever. But he couldn’t help himself. The hot college co-ed walked by and he craned his neck backward, in a way that only he thought subtle and inconspicuous. This is the quiet desperation Thoreau speaks of, and if you’re like most men there’s one night when that quiet desperation is at its peak: Halloween.

After a certain age, Halloween is no longer about collecting candy from strangers, trading Snickers for Twinkies, and complaining about how Gretchen the feminist hippy from down the block gave all the kids apples and toothbrushes this year. Once everyone’s raging adolescent sex hormones take over, Halloween becomes a competition between women over who can dress the sluttiest, and a competition between men over who gets to sleep with the slutty nurse in the short white skirt with the overflowing cleavage that’s been turning heads all evening. It’s a pagan holiday that sets the standard for hedonism in the young and horny, and I love it.

Dan Bilzerian – trust-fund baby, world-famous cretin, and the man dubbed ‘The King of Instagram’ – has carved out an entire career by having fake-breasted women follow him around the globe getting bottle service at glossy parties. He’s amassed millions of followers because he’s living the dream of every teenage boy, and merely by clicking the ‘follow’ button on Instagram, all these young men can live vicariously though his exploits. Halloween for a horny young man is like a snapshot of a Dan Bilzerian yacht party. It’s when the harem comes to you; the night when all the prettiest girls show off what they’re working with, and the not-so-pretty girls stay home and Netflix the entire back-catalog of their favorite TV show. Slutty nurse, slutty kitten, slutty nun, slutty teacher, slutty Pokémon character – there is no single object, inanimate or otherwise, that women cannot make into a slutty Halloween costume. Not to mention that where there are slutty Halloween costumes, there’s usually heavy drinking. Halloween and a Vegas pool party are the only two places when you can really experience the majesty of beautiful female twenty-somethings trying to outdo one another for attention-seeking objectification while at the same time throwing inhibitions to the wind. And a night like Halloween is especially enjoyable for a timid, socially inept fool like myself, because even if you don’t actually experience an emotional connection with another human being all evening, the mere potential to interact with such attractive eye candy is sometimes enough.

Despite all this potential, six years ago I put all my pre-conceived notions of Halloween aside and fell upon something special’ – something life changing. Halloween of 2010 was different, because that night I forgot about all the bullshit, and instead of being distracted by all the alluring knee-high stripper boots and bare midriffs, I started talking to the girl with the least sexy costume of all, and she turned out to be the most beautiful girl in the room, inside and out. That was the night I fell in love, and it wasn’t until three years later that I realized that she had the attraction of Medusa for a reason: She was The Devil Herself.

Falling in Love

Prior to falling in love I would hear those stupid cheesy things couples say to each other and they’d make me want to vomit, but after I fell I love, all those clichés turned out to be true. “They’re my special person,” “I’ve never felt this way before,” and for the diehard Cameron Crowe fans, “You complete me” – these are all pretty repulsive statements. Talk like that is for people that post their accomplishments on Facebook without thinking about how self-indulgent and narcissistic that is.

Hey, look at me! I got married!

I got employee of the month!

My baby is crawling now! Look at him drool! He’s so cute!

I’m on day 30 of my Paleo diet!

I started Crossfit!

Whether you’re falling in love or posting on Facebook, it’s important to remember one thing: Nobody gives a shit. You are posting those things to feel better about yourself, not because it’s an important life update. But then it happens: You fall in love, and you realize those ‘idiots’ who said that sappy crap and posted those obnoxious overshares were actually right. It doesn’t matter if no one gives a shit, because you want the world to know how happy you are anyway, so you say and do those stupid things and you blast out every shared meal and sunset beach walk to the entire Internet. Being in love causes you to lose all rationality. You don’t care if you appear insane because you lose sight of what sane looks like.

Three years after I met Lucifer – we’ll call her Lucy for short – my relationship was limping along like a wounded animal in the wilderness waiting to be snuffed from the Earth, and I finally realized that she didn’t want to be with me. Finally, she actually said the words, and I realized it was over.

Then I got depressed.

Then I vowed revenge.

Then I took my revenge out on every female I came across.

I went in search of as many women I could find that would fuck me, and when I found them, I fucked them. Because I’m a caveman. There’s nothing unique about a love story where someone gets their heart broken, but there is something unique about the way I responded: After I got my heart broken, I went on a hedonistic, unrestricted sex rampage of truly epic proportions. No one comes out of this story smelling sweet.

Before Halloween of 2010 (and before I met Lucy), people either used Match.com, eHarmony, JDate, BlackPeopleMeet, or they met each other the old fashioned way – drunk, in a bar. Four years later, after my relationship erupted into a flames like a block ton of shit hurling through the atmosphere towards Earth, the dating landscape involved a cold, heartless exchange over the Internet. The swipe-apps were invented, and dates were commoditized transactions as easy as Amazon’s 1-click shopping feature. (One minute you’re on Amazon, and the next thing you know you have a new pair of socks delivered to your door. One minute you’re on your smartphone, and the next thing you know you have a girlfriend. You get the idea.) Here’s the thing: I cracked the code. I figured out the formula of swiping, meeting, dating, and sleeping with the most gorgeous women on the Internet, and I became a sex addict. That is what this book is about: the before, during, and after of my relationship with the women that broke my heart. Or is it?

Strategies for Reading this Book

This could be a self-help book – an instruction manual for men on how to get laid in the post-swipe-app era. In the past year I learned a lot about women, dating, and how I went from bumbling loser to a guy juggling multiple girls at once, and sometimes juggling multiple girls, naked, in the same room. Somewhere in between that Halloween and when my relationship ended, a bunch of almost-teenagers capitalized on the appallingly obvious fact that the most important thing that people cared about when choosing a mate was how their partner looked. Tinder was invented. Then the plethora of swipe-apps took over and opened the floodgates for lonely, desperate, millennial daters. The four petulant twenty-somethings who created Tinder realized that taking 40 minutes to fill out a Match.com profile and then chatting for six weeks with someone you were lukewarm about was really irritating. Quickly, the dinosaur online-dating sites like Match.com, eHarmony and JDate were used only by the geriatric community. For millennials, it was Tinder, Hinge, Bumble, and whatever other new swiping apps were on the market. The never-ending tableau of potential mates made setting up a connection faster, easier, and more impersonal than ever. So if you’re a man like me who was once totally clueless about what attracts a woman, I’m here to tell you that I figured it out. Read on.

This book could also be a journey of self-discovery. But that’s unlikely, because then I would have to say things like, “I learned a lot about myself,” and “I really grew as a person,” and “I’m a changed man.” None of that would be true, because while I know I’ve changed merely because of the passage of time, I’m not sure I grew much. I’d like to think I’ve come out the other end of this colonic shit-storm of relationship disasters as a better person, but I doubt it. Perhaps the only certainty I have in all of this is what the poet Robert Frost once said about life: “It goes on.” Thank God, because I’ve got a lot to regret.

Maybe this is a book about general dating advice, but that’s not quite right either, because every romantic exchange – even the simplest and most impersonal sexual encounter – is unique, and anyone that says there’s a formula or theory for figuring out relationships is full of shit. You can talk about it until you’re blue in the face, but you won’t find some magic combination of words or behavior or pheromone spray or outfit that’s going to lead to blissed-out relationship happiness. That’s because how you might act with one person could have the totally opposite effect with the next person you meet. Each will have different tastes, energy, personality, and preferences. So even when you think you grow and learn after falling in love, in reality you can pretty much throw everything you think you’ve learned out the window. Maybe you learn some basics, like how to be unselfish, or how to put the toilet seat down after peeing, or how it’s a bad idea to sleep with other people and not tell your partner, but in terms of big meta-level principles that you can apply wholesale, you will forever be in the dark on that stuff, because that’s what love is – it’s fumbling around in the dark with another person, totally naked, and hoping that they don’t all of a sudden knife you in the back, Fatal Attraction-style. But no one tells you that. So that’s also not this book.

Lastly, I’d like to dispel any notion that this book is attempting to be any sort of serious social commentary on dating, because I’m not smart enough for that project, so I’m just going to stick with what happened. I will say that my two years on the swipe-apps vacillated between raucous, wild, unforgettably fun sport-fucking and deep, dark, crushing depression. Between falling in love, getting my heart broken, and re-inventing myself as someone who is attractive to the opposite sex, I had to hit rock bottom along the way. A few times. Plus, sometimes the most fun comes from the most miserable of circumstances, and while people can have differing opinions on the merits of locking yourself in your bedroom after a particularly bad date, blasting Peter Gabriel’s In Your Eyes at full volume, and pouring an entire bottle of whisky all over your naked body, I speak from experience when I tell you that while it seems pretty miserable, it can also be fun.

Chapter One



Part One: Your Real-life Profile

When your parents mashed their genitals together all those years ago, they pretty much sealed your fate as to who you’d become. Maybe you’ve got a crooked nose, or you’re 40 pounds overweight, or maybe you’re 300 pounds overweight and you’re a former contestant on The Biggest Loser. Congratulations. The point is, we’ve all got faults. The difference between people who do well in the world of real-life dating and the people who don’t is the difference between people who do a good job of hiding their flaws and those who don’t. I don’t care how ‘honest’ you think you’re being, there’s no sense in leading with your worst attributes first. Nobody wants to hear or see or know or care about all your bad shit right up front. In the 1980s when they were selling those cars with the engine that blew up after a minor fender-bender, they weren’t leading their ad campaigns by telling prospective buyers that there was a really good chance they’d be engulfed in a fireball and burnt to toast in the event of a minor accident. Skydiving schools don’t plaster promotional material with info about how you might wind up with your guts splattered all over some anonymous cornfield when your parachute doesn’t deploy properly. That info is in eight-point font on the back page of some legal waiver they hand you right before you get in the airplane.

The point is, the person you’re trying to have sex with is probably going to find out about the bad stuff eventually, so there’s no sense in leading with it. While this may seem obvious, I have plenty of friends who will come right out and say how they are needy, or pushy, or how they’ve gained a little weight, or how they have a massive fucking forehead that you could land a 747 on. Even if these things are true and it makes you feel better about your flaws to disclose them right up front, it’s not helping you in the long run, so stop it.

I’ve got my fair share of shitty attributes, and I had success with women after I was sacked by the woman I loved because I learned how to hide them, or at least didn’t lead with them up front. Here’s all the shit I didn’t want women to know about me, and I hid from them for as long as I could:


First of all, my head is way too big for my body. There was a kid in high school who actually called me ‘big head.’ He tormented me, and it was around the same time the actor Mike Myers starred in the phenomenal 1990s movie So I Married an Axe Murderer. The movie had a very funny string of jokes ripping on a character with an enormous head, and in what was fortuitous timing for my bully, fans of the movie, and fans of bullying in general they got to enjoy the jokes all over again at my expense. Every little snot-nosed high schooler within ear shot of his insults directed at me found them hilarious, and he did it so much that I started wearing hooded sweatshirts, hats, and anything else I could to distract people from the obvious fact that he was right – my head was too big for my body.

The worst insults are the ones that are true, and this was no exception. My head is still too big for my body; I look like a bobble head. (Sidenote: As if that wasn’t enough, Mr Bully ended up marrying my fifth grade crush, who I wrote a very nice love poem for when we were in elementary school, and she also humiliated me by passing that love poem around at recess. I can still see the group of fifth-grade girls huddled around my poem, pointing and laughing at me, while I stood alone in the middle of the asphalt playground, mortified. I guess they were a perfect match.)

I also have a bit of a potbelly. Do you think I spend a lot of first dates at the water park, prancing around with my shirt off, or at a couple’s massage? No, I fucking don’t. I wear an untucked button-up shirt and if the little paunch in my stomach ever comes up, I say something about the fact that I have a back problem that effects my posture, and my belly isn’t really that big. My giant head or medium-sized potbelly are way less devastating to my chances of getting laid if it comes up on the third, fourth, or fifth date, because she’s already invested in the relationship by that point. Who knows, I might have already won her over with my charming personality or the fact that I have a stable job.

That’s not all. I also have tiny feet, which is a really weird attribute to have as a man, especially because I’m above-average height at six foot two. There may or may not be scientific proof about how having tiny feet affects other male body parts, but it’s absolutely true for me, because I’ve got a minuscule little pecker. I suppose it could be worse, but the problem is, unless I intend to live a life as a celibate monk, each sexual partner I have is going to have to come to terms with the fact that my penis is like an engorged pinky finger. I never read the runaway best seller Fifty Shades of Grey, but I’ve heard reference to the male character’s anatomy as various large oblong vegetables, construction piping, military ordnance, and many other phallic objects. In that same vein, you can imagine my piece as somewhere between a tiny Oscar Meyer wiener and an old fashioned No. 2 pencil. Put the least flattering aspects of those two items together, and you have a pretty good idea of what I’m packing. With each sexual encounter, I have to relive the shame and embarrassment of my little guy downstairs, including enduring the look on my partner’s face when they realized they would have been better off masturbating with a dildo at home than spending the night with me.

Maybe this isn’t technically part of the ‘first impression’ you give a woman, or part of your personal profile unless you have some extremely unorthodox dating methods that include potential criminal charges for indecent exposure, but having a tiny penis impacts everything a man does in his life. Namely, it almost always significantly affects the single most important attribute you can have that will lead to success in dating: Confidence. Women want a man who walks right up to them, looks them in the eye, and is so overflowing with self-assurance that it puts them on their heels. They want someone who looks like they’re going to take control in bed, and then when the lights go out, actually does. If you’re like me and you have a tiny penis, the only thing you are projecting is neurotic anxiety. The idea of eventually getting naked and having to deal with her being let down is like having that dream where you’re naked at school on stage during assembly. It’s embarrassing.

Let me pause here to acknowledge that I realize that all men think they have a small penis, and so maybe you think I’m exaggerating, but trust me – I’ve done a lot of research on this, and I promise you I’m not being hyperbolic. I once had a girl say to me “I love sucking your big cock” while she was sucking my not-big cock, and when I looked down at her gorgeous lips wrapped around my tiny little member and smiled wryly at how preposterous that statement was, she didn’t just smile back in agreement, she actually laughed. You could tell it was something she said every time she had a dick in her mouth, so I didn’t hold it against her, and the fact that she was willing to even put my pathetic manhood in her mouth in the first place pretty much gave her a free pass to react however she wanted. Plus, that was a lot better than the time a girl actually stopped sucking my dick, tucked it back into my shorts, and said, “I think that’s all for now” with a very disappointed look on her face.

The point of all this is that I am living proof that there are almost no physical flaws that you can’t overcome. Despite my giant head, medium potbelly, and tiny penis, I still got on the swipe-apps and absolutely destroyed it.

The Nice Guy

If you were to poll every woman I’ve ever dated, they would describe me using one word: ‘Nice,’ and for the most part they’d be right. While it would be empowering to walk into a room and not give one single flying fuck if anyone liked me, I’m not that guy. I’m a people-pleaser who cares deeply about what others think of me and who wants everyone I’m hanging out with to feel loved. I’m the Nice Guy – the guy women date after a seemingly endless string of losers, assholes, über-confident megalomaniac Wall Street bankers, superstar athletes, and otherwise douchey men that that are apparently most desirable to women. It’s no fun being the Nice Guy, because the Nice Guy only gets the leftovers. He gets women once they lower their standards and resign themselves to a life of boredom, disappointment, and disillusionment. Women are not attracted to the Nice Guy because he has no edge, and he lacks both initiative and confidence. They don’t respect him, and the Nice Guy doesn’t get laid by beautiful women until those women date enough assholes to arrive at that ‘Aha!’ moment when they realize dating someone with a neck tattoo and a rap sheet as long as a CVS Pharmacy receipt does not translate into long-term happiness. Meanwhile, Mr Neck Tattoo gets to fuck all the prettiest girls, ride around on his motorcycle wearing his leather jacket, commit petty offenses, and be objectionable to everyone in his orbit. Growing up, I was always the doting boyfriend, the attentive, monogamous, needy, accommodating push-over that yearned for reciprocated love while having to watch my more bad-boy friends and associates attract our best-looking classmates like flies on shit.

Before my relationship with Lucy, I thought the best way to get the girl was to be kind, caring, and gentle – sort of a Golden Rule philosophy to dating. I was wrong, and it didn’t work. Then I got my heart broken, said ‘fuck it,’ and all of a sudden I adopted Mr Neck Tattoo’s personality and became the asshole douchebag that women went to war over. It used to infuriate me when women said they liked that I was Nice, but I understand it now. I understand that it makes no sense, it never will, and if women want a guy who lies, cheats, steals, and manipulates his way into her pants, I’m willing to take advantage of that backasswards logic to exploit it. So that’s what I did. But first, before I met Lucy and while I was dating her, I was Nice. And maybe that was the problem.

Being a Creep, Losing My Virginity, and Making Conversation

The voyeuristic pleasure of imagining people’s bedroom behavior has always captivated me, and I don’t understand why everyone isn’t as fascinated with sex as I am. I’m simultaneously obsessed with it but terrified and intimidated by women at the same time. There is a certain class of beauty that leaves me breathless, and while I know this is due in large part to my tiny Johnson, it’s also because like most males that grew up in the digital age, I’ve seen a lot of porn – a lot of unnaturally large male genitalia, a lot of degrading, unrealistic sex acts, and a lot of shockingly intense verbalizations of fake euphoric pleasure from some aesthetically pleasing females. Lack of confidence, the prevalence of pornography, and a predisposed curiosity towards sexual deviance combine to make every interaction I have with a beautiful woman an exercise in embarrassment triage. If you’re a female wearing makeup, smell nice, and you’re between 18 and 30 and not morbidly obese, chances are if our paths cross my throat will constrict, I’ll get sick to my stomach, and it’s 50-50 on whether or not I’ll throw up on you like that South Park character does every time he sees his crush. This is true whether said-woman is standing in front of my face or on a football field so far away I can barely make out their profile or, more importantly, the size of her tits. My heart will stop, I will not be able to breath, I can’t remember my name, and I’ll get the feeling that the world could implode at any moment.

As men age, this feeling only intensifies, and if you have ever wondered why men are so creepy, it’s because this inability to function overpowers the social norms necessary to keep woman feeling safe. The only thing preventing an old creepy man from leering at someone a third of their age is social impropriety, and oftentimes they disregard even that. This urge is pathetic, inconsiderate, and uncool. But it’s also uncontrollable. I only know because I suffer from it myself. There’s a very fine line between being a creep and delivering a suave pick-up line, and often the only difference is whether or not she likes it.

I also walk the fine line between normal human being and disturbing sexual predator because I did everything late. I was 11 years old and on a family vacation at a friend’s cabin when I got my first boner and it wasn’t until I was almost 20 that I finally got laid. I remember that first erection like it was yesterday, and I knew right away I was going to have a problem. Some older teenage kids were passing around an X-rated comic strip with a naked cartoon lady arching her back in orgasm while she rode a cartoon man’s cock. All of a sudden I was rock-hard and my brain was on fire. This character’s enormous black-and-white cartoon boobs were so arousing that I had to wait until my friends had scattered to do other activities so I could scoop up the magazine and find an empty room in the cabin. I rubbed my tiny little stiff shlong against a pillow for the next 40 minutes, with nothing more going on in my brain other than the pure, cocaine-level endorphin rush unique to sex. My dick remained red and swollen the entire week of the trip, and ever since that first little pre-teen erection, my sex drive has only increased, keeping pace well into my 30s.

Through high school I watched friends, friends of friends, and the more socially well-adjusted kids pair off to enjoy the inevitable experimentation that contributes to a healthy adolescent sex life. Meanwhile, I was an introverted pervert weirdo who needed to jerk off twice a day just to be able to complete a sentence when called on in class. Probably the first dozen or so times I made out with a girl, I had to get so appallingly drunk to overcome my fears that I couldn’t stay vertical enough to do more than graze her cheek with my tongue on my way to the floor. Maybe I shouldn’t have been drinking heavily as a 12-year-old, but I suppose alcohol abuse should be the subject of my next book. This is my sex addiction book.

Once I did have sex, I was in for a rude surprise. You would think someone with record-breaking masturbation habits would have built enough calluses on their genitals to last more than five seconds in bed once they found a willing vagina. Not so. I was two months shy of my 19th birthday and at Fresno City College in bed with the sweet and pleasant Big-Boobed Becky in my tiny one bedroom apartment. I remember removing her clothes and after a brief, hushed conversation establishing that she was on birth control, I slide inside her. How incredible the warm, tight embrace of a friendly snatch feels when your dick is inside it is something women can never relate to, but it’s probably like a dozen puppies being released during the climactic scene of a Shonda Rhimes sitcom while being spoon-fed Ben & Jerry’s ice cream. So when I slide inside Becky after what seemed like hours of foreplay (but was probably only about ten seconds), and her young, sweet, tight little vagina clamped down on my tiny pecker, I immediately came inside her. She laid there, stunned, disappointed, and somewhat confused, until I shamefully rolled off, apologized profusely, and confessed that I was a virgin. I wish I could say my performance improved over the years, but sadly my love life is like if Jonathan Franzen wrote the sex scenes for Fifty Shades of Grey – all the characters are inadequate, cynical, and disappointed in each other.

I’m also one of those people who has the uncanny ability to make an awkward situation even more uncomfortable. Once I was of age, I rarely reneged on an opportunity to be in the presence of pretty girls, even though my best chance of actual interaction was if one of them spilled their drink on me, and I’d get five seconds of pity before she wandered off to a group of guys in tight T-shirts. At some point enough was enough and I started making more of an effort, but most of these tragic encounters ended with her hoping I would implode into a cloud of dust or be escorted off by security, while I silently contemplated what I should say next after my classic ‘you’re pretty’ opener. I’m not exactly what you’d call a great conversationalist.

My Parents

Finally, to round out my general emotional confusion about love, I have to talk about my parents. My parents are a fantastic example of what love should not be, and I probably never believed in love before I met Lucy because I never had a great example of what it was supposed to look like. My parents were both previously married, and things did not go well for either of them. My dad’s first marriage lasted about six months before his nurse wife cheated on him with a doctor, and my mom’s first marriage lasted eight years, produced three kids, and ended when her husband doctor cheated on her with a nurse. In a missed opportunity for a really compelling plot twist, my dad’s first wife and my mom’s first husband did not have an affair together. That would be too good. Every time I go see a doctor now I picture him walking out of my examination room, finding the first attractive nurse he comes across, whisking her away into a hallway so he can bend her over the nearest gurney to pound away doggy style in a hurried rush so he can get to his next patient. Based on my sample size of one cheating doctor and one cheating nurse, I imagine that hospitals are stuffed full of people fucking all day long and no one really ever gets to the business of healing people. If the plot to Grey’s Anatomy and my parents lives are any indication, that’s probably about right.

After my emotionally-damaged parents split from their cheating spouses, they drifted around like everyone does in their late twenties and early thirties, each wondering independently if they would ever get re-married or just die alone in a drab motel room smelling of piss. When they met they were both single and well into their thirties. My mom was living in the small northern California town of Redding with her three kids in a nice house that she was able to buy with money from her divorce settlement. My dad had just moved to town to start a new job as a young lawyer in the county public defender’s office. They met at church, and I’ve never asked them but I’m guessing by the time their paths crossed they were probably disillusioned and cynical of the dating scene, and they were probably tired of being lonely, so they did what it seems like everyone does at that age – they just settled. They gave up the hunt and got married. This is not entirely a guess on my part, because I once asked my dad why he married my mom and he just sort of shrugged and said, “it just made sense.” Pretty romantic, huh? I’m pretty sure my dad’s proposal was them sitting around on a Tuesday night, when he just looked over and said, “Wanna get married?” As you can imagine, MOM WAS PISSED!

But what was she going to do? She was a divorcée with three kids living in a large lonely house in Redding. She was going back to school to be a nurse, but didn’t really love the idea of working, and the dating pool for a divorced woman with three kids was not exactly flourishing in the late 70s/early 80s. Also, I’m sure that raising three kids in that giant house in some small northern California town was lonely. And who came blame my dad? His first marriage ended with him being cuckolded less than six months after reciting his vows. If he was a little jaded or a bit cynical, I can understand why.

My parents’ marriage wasn’t under the best of circumstances, and after mutually agreeing to quell their loneliness by tying the knot without every really determining if they were right for each other, they slogged through the next 30 years until they became too old to give a shit about what the other person looked like or how they acted, and they finally fell in love. You see, prior to them growing old and accepting that they needed the other person in their life, there were epic fights, they went weeks and weeks without speaking to each other, interspersed with tense, muttered exchanges peppered with expletives, and there was the occasional item of kitchen ware thrown at my dad’s face when he strolled in after eight o’clock smelling of cheap perfume. Bored and disappointed with his life, he decided to turn himself into the ultimate cliché hypocrite and had an affair with his secretary.

While the train wreck of my childhood unfolded like a very familiar, very privileged reality TV show that would probably have been called something like White People Problems, my response was to disappear. Even at that age I could tell that what seemed like a nice middle-class Leave It to Beaver experience was actually really fucked up, so I just ignored everyone and escaped to go hang out with my friends or play sports. I was a loner who didn’t believe in love. As mentioned I had a tiny penis and an enormous head, I was cynical and neurotic, I was totally incapable of talking to women, and I’d been witness to years of my parents’ horrendous example of what a marriage should look like, yet when I finally met the love of my life that Halloween night, she still accepted me. The magical formula for finding someone to love really comes down to this: Recognizing the flaws in each other and saying, “okay.”

Back to the Beginning

To top it off, right around the time of Halloween 2010 I was having a quarter-life crisis. This is probably how every law student feels, but after receiving very mediocre first year grades, I moved out of my apartment, sold or gave away almost all of my furniture, and moved in with two of my closest law school friends, Jordan and Drew. They said they liked having me around, but I think they could see the desperation in my eyes and realized that they were either going to have to put me on suicide watch or let me sleep on their living room floor. They went with the living room floor.

Each morning I propped my mattress up on the side wall of their living room and each night before bed I laid it smack dab in the middle of the floor, got my comforter out of the closet, and slept like a roadie drifter in a rock band. I planned to finish out the semester, go home to northern California, announce to my parents I was done with law school, and travel the world as a vagabond to ‘find myself’ – sort of like a male version of the memoir and chick flick Wild. Who knows, maybe I needed to travel to Italy, hike the Pacific Crest Trail, or do a bunch of heroin and fuck a guy named Paul. Either way, my life circumstances on the eve of that 2010 Halloween did not exactly portray someone who might be suitable boyfriend material, so when Lucy recognized the flaws in me and said ‘okay’ anyway, I was pretty amazed.

Once Jordan and I decided to go out on the night of October 31, 2010, we had to put together last-minute costume choices. I connected a huge ring of keys together, threw on a baseball hat and slacks, an oversized blue Waste Management polo shirt from the summer I worked at the Landscape and Refuse department of my college, grabbed a mop, and voila! – I was a janitor. Jordan went as a baseball player.

The dank Los Angeles bar hosting this Halloween bash smelled like piss, and neon strobe lights illuminated the small packs of young professionals looking to make bad decisions. Right away we bumped into our mutual friend Hillary. She was dressed in pigtails, a little league shirt, and sneakers to complete her slutty elementary school student costume. Her friend, who I’d never seen before, had short blonde hair, a round, innocent-looking chubby face, and her mouth curled upward in kind of a wry smile. She wore a red cardigan sweater with a boy’s T-shirt under it, jeans, and tennis shoes. Hillary introduced us and when I looked into her eyes, my mind went blank. Maybe I’d built up enough liquid courage, or maybe I was comfortable because Hillary had made the introduction, but somehow when I opened my mouth, actual words came out.

“What are you supposed to be?” I asked.

“Mr Rogers!” she said.

I looked around at the slutty nurses, slutty vampires, slutty Sesame Street characters, and right away I was smitten. Here was a girl dressed as the most asexual male children’s show host of all time, and somehow that unique costume choice accentuated her beauty even more. She was original. Her name sounded like it was from many decades ago and didn’t seem to fit her, like a character out of a Jane Austen novel, and I’d say it here but I can already envision the lawsuits that might follow, so let’s just stick with calling her Lucy.

I made a couple of jokes that were the kind people only found funny in a loud bar after everyone has started to leak alcohol through their pores. The interaction was about as good as any conversation at a bar can be – mostly just shouting back and forth at each other over the raucous music and chatter, but there was some inexplicable connection. We danced, drank, joked, laughed, and drank some more, until we were sitting alone at a booth against the wall. I could count the nervous beats of my heart as I looked out among the clutter of costumes. Then I looked over at her, leaned in, and went for the kiss. She met me halfway, and it was magic.

All of a sudden the lights came on and everyone scattered like rats in an Italian kitchen. Hillary grabbed Lucy’s arm and announced a cab was waiting outside. Not wanting the night to end, I did what any psychotic serial killer with no regard for human social norms would do – I followed her. Whether it was the third-party validation of having Hillary’s approval, or the fact that we were just sucking face and Lucy actually liked me, for whatever reason they both seemed okay with it. We arrived back at Lucy’s. Hillary immediately went to her bed while Lucy and I sat on the couch in the living room and had a whispered conversation about how fun the night was. She made popcorn, asked if I wanted some, and when I declined because I said I didn’t like it getting stuck in my teeth, she laughed. Ding! She got the bowl out of the microwave and sat next to me. In that moment, in her small apartment on her shitty couch, I didn’t care about anything other than just being there with her. I didn’t care about eating popcorn, about hooking up more, or flunking law school and disappointing my parent. I just wanted to be with her.

I suppose the typical male response in this situation would have been to grab the popcorn bowl out of her hands, set it down, cradle her neck in my hands and go in for another kiss; then fondle her tits and try to strip her clothes off so I could get laid. But sex was the last thing on my mind that night. Not just because the fear of embarrassment at completing the act, but because being there with her was enough. So when she told me she had to kick me out soon and that we wouldn’t be having sex, I was relieved.

The Beginning and the End

The clarity with which I remember that first evening is because I’d come to love her so much over the following months, and we’d spend the next four years inextricably entwined in each other’s lives. The things I learned about her that night and in the weeks that followed turned me into that mushy, sappy, lovelorn romantic comedy trope of a man that every single person despises and never thinks he’ll become. This is how most real-life introductions work – the right place, the right time, the right introduction from the right friend. Mostly wild happenstance, really. I just stumbled into it.

Maybe love is just a cure for loneliness, and maybe I just fell in love because I was lonely, but sitting in that small, cramped apartment that Halloween night, everything felt right with the world and that feeling was different to anything I’d ever known. It was more than just infatuation. I could see a future, and if I could go back and live in that moment forever, I would. Instead, four years went by, the relationship crumbled into a mess of desperate pleas, visceral emotions, and countless nights of tearful rumination on everything and anything that went wrong between us. Sitting in that apartment, how could I have known that four years later I’d be crying my eyes out, begging her not to leave me, and wishing we’d never met?

I’ve never been able to recapture the magic of that evening or the feeling that life could be infinite. So when she broke my heart and things ended for good, I had an impossible void to fill. I was bitter, angry, resentful, and depressed. I turned to online dating, and I did it with a vengeance.

Part Two: A Beginners Guide to Dating on the Swipe-apps

A Note about Apps

In the year 2000, some UC Berkeley PhD candidate launched the website HOTorNOT, where users would rate a random photo that popped up on the screen on a scale of one to ten. Every single swipe-app is based on a remarkably similar concept to HOTorNOT, except that instead of rating people, you swipe right if you would like to bone them, and swipe left if you don’t. And if both people swipe right on each other’s picture, you can start texting. How the founders of HOTorNOT got beat to the market by Tinder I have no idea, because the HOTorNOT website still exists, and although I didn’t set up an account for fear of getting a virus, it appears that HOTorNOT is realizing they missed the boat, and is now totally copying Tinder. Or maybe Tinder is copying HOTorNOT and they’re just doing it better. Who knows? The point of these apps is that everyone is shallow, and a lot of people care immensely about the attractiveness of their partner.

By the time I finish this book, I’m sure that people won’t even interact in person anymore, everyone will be riding hoverboards and men will be sticking their dicks in machines instead of actually having sex. However, among the vast landscape of available swipe-app options, there are a few worth mentioning, and it can be overwhelming if you’re just starting out. Let me help you.


If you used Tinder when it first came out and never paid them a dime, you win. Anyone paying for Tinder is missing the point, because paying $8 a month so you can ‘swipe anywhere’ and connect with someone that lives in Papa New Guinea, or ‘super like’ someone to emphasize just how desperate you are, is not going to help you find love, sex, companionship, or anything in between. If you’re not getting matches without all that premium bullshit they want you to pay for, that stuff is not going to put you in pole position. If you have or if you’re going to pay for a premium membership to a swipe-app, you need to delete that shit instead and start trolling the local bookstore for attractive mates. Paying for Tinder is like paying for a hooker without getting off – it’s a lot of anticipation and excitement that will ultimately leave you dissatisfied and maybe even homicidal. And you might get blue balls in the process.

Tinder, like every single Internet dating platform that came before it, was successful because of marketing. Tinder recruited attractive college kids, and if you’re going to market an app that is solely based on looks and attractiveness as a way to meet people, you’re going to want a bunch of gorgeous, attractive, tanned college kids as the talent pool you choose from. Tinder appeals to our most superficial and base instincts, made it acceptable, and in the process made online dating cool. Match.com was stigmatized because it was full of desperate losers, whereas Tinder was more like a fun game of HOTorNOT that could actually match you with people who might fuck you. All of a sudden attractive people with voyeuristic tendencies could whip out their phones and swipe in every direction all day and all night.

Sadly, now that tinder has become the giant of dating apps and started to try to monetize their platform, the talent pool has been diluted and the quality of potential mates has deteriorated markedly. These days Tinder is full of misshapen, too tall, too thin, too short, too ugly people who do not have the luxury of going out into the world and just waiting for someone to hit on them. Tinder has become the new Match.com – the dating platform used by people to find love who are desperate, ugly, and/or stupid. Sadly, Tinder has succumbed to the inevitable lifecycle of an online dating company that lost the demographic that allowed it to be a successful app based solely on superficiality: Attractive people. Now that Tinder is full of normal human beings and not the gorgeous, attractive, tanned college kids that populated it in the beginning, it is dead.


This is an idea that never took off. Hinge paired people only if they had some connection via their mutual friends. This seems like a pretty good idea – women might feel more comfortable if they share a mutual connection with the creepy dude they’ve matched with. They might think, “He’s probably not a serial killer… he knows my high school chemistry partner Doug!” The problem is, if you’re using dating apps, you don’t necessarily want your friends to know. There’s less of a stigma these days and it’s okay to have met your partner online, but you don’t necessarily want to publicize it. For some it’s an admission of desperation. Also, Hinge connects users via the friends-of-friends model, but if you wanted to meet a person to have sex with through friends-of-friends, you would just do it in real life. You don’t need the Internet for that. The swipe-apps are basically the late-night bar equivalent of finding a random and hoping it all works out. People like this format of randomness because if it doesn’t work out, no love is lost, no one chooses sides, and no friendships become fractured. Hinge needlessly complicates things. Finally, requiring people to have a mutual friend in common limits the pool of available options. It also takes the fun away of matching with a random stranger that you nevertheless might have a connection with. I’m pretty convinced that no one actually met in real life after using Hinge. If you’re on it, you’re probably wasting your time.


In the wake of a corporate love triangle at Tinder HQ that involved overt racism, spoiled rich kids, junior-high level critical thinking skills, and a million-dollar sexual harassment lawsuit, one of the female founders parted ways with the company and created Bumble. The idea behind Bumble was to empower women, so when the sexual harassment victim of the Tinder love triangle fiasco received an enormous sexual harassment settlement, she decided to do the exact same thing as Tinder, but sell it to women. Literally the only difference between Bumble and Tinder is that the woman has to start the conversation. This might seem like a good idea, but every girlfriend I’ve ever had needs two hours to determine what she’s going to wear before leaving the house, then she can’t decide what to eat at dinner, and then she changes her mind 47 times as to whether or not she wants to stop for ice cream on the way home. So good luck getting women to make a decision on what man she wants. Fortunately, once the women says ‘hello,’ she no longer has to initiate. Otherwise, no matchmaking would ever get done on Bumble.

Also, while the goal was to ‘empower women,’ Bumble actually did the opposite. Putting the pressure on women to open a conversation subjected them to the same paralyzing fear and shame of starting a conversation and getting stonewalled that men face. They also have to deal with the frustration of matching with someone and getting unmatched. Bumble made men the commodity to be desired, not the other way around, and while I love Bumble, it’s a comical irony that what the founder intended actually had the opposite effect. It’s my favorite swiping app because, being a man, it requires the least amount of effort. You can swipe right for 48 hours straight, get as many ego-boosting matches as you like, and pick and choose who you respond to. Thank you, Bumble founder.

(Then again, I thought Instagram was a stupid idea, and those guys are all surfing down piles of gold coins Scrooge McDuck-style, so what do I know?)

All the Other Apps

There are a lot of other apps. I think pretty much everyone has adopted some version of the swipe left or swipe right, snap-judgment instantaneous match-making process. I didn’t use any of these, so I’m not going to talk about them, but if you’re on Plenty of Fish, OkCupid, Match.com, JDate, The League, BlackPeopleMeet, Farmer’s Only, or Graveyard Shift Employee Love Connection, just be advised that the longer the site has been around, the shittier the quality of people you have to wade through to find someone worthwhile. Listing every single app out there could probably fill all the pages in this book, and nobody has time for that shit.

My Internet Dating History

My ten-year-old nephew got a cell phone before I did, and when in 2003 I finally purchased a Nokia flip phone, people were texting, sexting, and probably well on their way to developing the first mobile ‘apps.’ So when I finally upgraded to a smartphone years later, discovering the array of social media options was overwhelming. I delayed the upgrade for so long because I knew I’d develop a social media addiction rivaling an intravenous heroin user, and when I finally did get online, this was confirmed when I discovered Instagram. It’s an incredible phenomenon that porn-star hot women can make their living hawking swimwear, protein drinks, and herbal diet teas all because they purchased a pair of fake breasts, hired a professional photographer, and/or worked out how to take sexy selfies. The Internet is not a productive place to spend your time if you’re like me and you’re addicted to beautiful women and have the attention span of a gnat. One minute I’d be looking at funny memes and the next minute I’d be gawking at a topless 18-year-old in booty shorts. Something tells me I’m not alone. Yet the benefit of the swipe-apps is that they allowed a calmer, more dignified way of meeting people other than getting piss-drunk and stumbling around a club hoping some girl would take pity on me and offer up a blowjob. It just took me a while before I got on there.

The Online Profile

Sometime in the fall of 2014, I started with Tinder and built my profile with what I thought were the best pictures I had. I provided some genuine information in the About Me section and linked the account to my Facebook, probably forever giving Mark Zuckerberg the ability to take total control over my life, and I prayed for the best. Results were tragic. I went on so few dates that I figured I was better off throwing my phone at the next attractive girl I saw in public and then asking her out when I visited her in the hospital to inquire about the head laceration she suffered. I finally showed my profile to a friend for some feedback. He immediately burst out laughing.

“What?” I asked.

“You look like a serial killer.”

“Maybe that’s what I’m going for…”

“It’s working.”

“Okay, I’ll change it.”

Turns out I’m not a very good judge of which photos I look good in, and I’m not very photogenic in the first place, so I turned to the one person I knew could give me some style and appearance tips: My Gay Friend James. If you have a Gay Friend James, meaning someone who is attractive, funny, smart, interesting, and also mildly annoying in an overbearing way, that person should create your profile. Gay men have impeccable taste, and given that James is also attracted to men, he was the perfect profile architect. (Sidenote: The same is not true with dykes. Only use a lesbian to create your profile if you want photos of you in Birkenstocks, cargo shorts, wool socks, a hunting cap and fly-fishing vest, standing next to a Subaru.)

In the absence of someone like James in your life, I’m sure it would be nice to have some data points, so I’m going to give you a few tips for constructing your online profile, especially the common mistakes to avoid. Most of this advice also applies to the ladies, given how many female Internet dating profiles I’ve seen over the last couple of years. There are some obvious red flags, some overused themes, and there are more than a couple of failsafe techniques to get more potential matches to swipe right.

The Pictures

There’s a fine line between outright deception and putting your best foot forward, and you’re not doing yourself any favors by skirting this line, because you’re eventually going to have to have a real-life interaction, so over-selling your attractiveness is not always in your best interest. Go ahead and throw a filter on your photos, but don’t get carried away by only posting The Greatest Photo Ever Taken of You. Otherwise, when your date shows up, they might just turn around and leave on the spot. This has happened. I’m not saying who did it, or when, but it’s happened.

For men: Don’t get too hung up on the pictures because there’s a certain threshold of attractiveness you have to meet, and once you’ve met that threshold it’s all about what your profession is/how much money you make. Women’s tastes are so varying that it’s impossible to know what they want, unless you can dance like Channing Tatum, look like Brad Pitt, and you’re a millionaire. This is what’s called The Low Male Hotness Threshold, and it is responsible for the most confounding phenomena in the dating world: The Overachieving Male. Also, if we were to isolate personality as a variable, the formula is simple: The more money you have, the better. If you’re the hottest guy on the planet, you probably don’t need to be a millionaire or billionaire – you’re doing just fine. And for the average Joe, you’re somewhere in between. The Overachieving Male is way more prevalent than the Overachieving Female, and when you see the Instagram feed of a gorgeous girl wearing a skimpy bikini on a yacht, it’s important to remember who owns the yacht – it’s a fat hairy dude in a banana hammock who probably inherited his money or lives in an oil-rich country where everyone is born a millionaire. Women want an attractive mate, unless you’re a loaded Sugar Daddy who spends half the year sailing around the Mediterranean. Here is a graph for reference:

Now that that’s out of the way, here are three simple tips for men’s profile pictures:

1) No shirtless selfies. Shirtless selfies are so 1990, and unless you’re hanging out at the beach with some buddies or playing a sport, you’re going to significantly limit the pool of women who are interested if your profile picture is the straight up bathroom selfie. You look like an idiot. The no shirtless selfies policy applies to the fittest meathead with a body from the movie 300 (which, coincidentally, is that movie’s score out of 10 for gayness), and it applies to the fit, but not super ripped, runner who wants to show off that he works out despite his fulltime job. I know you’ve put in a lot of hard work at the gym and I’m sure you look great naked, but the shirtless selfie makes it seem like that’s the only thing going for you. It also suggests that you’re a douchebag.

2) Smile. It’s okay to show that you can have a good time, and you’re much less likely to look like a serial killer if you have a nice genuine smile. From what my female friends tell me, and from James’ assessment, apparently some people need this advice. Or even if your smile sucks, you’re still better off looking like a nice, fun person than someone who has a stick up their ass. If you take yourself too seriously, women are probably not going to be into that. Remember, chicks don’t dig serial killers, and if they do you probably don’t want to poke that.

3) Careful of pictures that feature one other female, unless it’s your sister or your mom. Girls are going to compare themselves, and you don’t want your potential date feeling any more insecure about herself than she already is prior to meeting you. Also, don’t post pictures of you with your ex, because women will think you’re obsessive. Because you are obsessive.

Posting the right pictures really boils down to the need for third-party opinions. Good luck.

For women: Desirable qualities in women boil down to two factors: Is she pretty? and: Is she smart? The second is negotiable. There’s a reason why breastaurants exist, and there’s a reason why gorgeous females who can’t do basic arithmetic move to Hollywood and all of a sudden make millions of dollars being ‘actors,’ and there’s a reason why Professional Instagram Models exist. Not every woman out there has won the genetic lottery, and adhering to some basic rules when it comes to building your online profile can do wonders. Here are some key points:

1) The more recent, the better. A good general rule of thumb is that no picture should be more than two years old. As I’ve said, the in-person meet-up is inevitable, and there’s nothing worse than going through all that messaging and texting and then having your date be woefully disappointed by your in-person appearance because you look less like Blake Lively and more like your average Wal-Mart employee, complete with skin-tight black pants and blue vest. Using an old photo is lying, and that’s no way to start a relationship. And while you might think differently, you do not look the same as you did two years ago. That photo from five years ago where you had the perfect skin, perky tits, and the youthful glint in your eyes? You cannot use that anymore. The more you violate this rule, the more your date will resent you for leading off with a gross misrepresentation about arguably the most important thing: How you look. (Yes, you heard that correctly. How you look is the most important thing about you, and if you think differently the millions of people using swipe-apps disagree with you.)

2) For the love of God, if you’re using a group photo, crop out your gorgeous friend. It never ceases to amaze me how often this rule is violated. And if you have nothing but gorgeous friends, you need to find new friends. Every single dude that looks at your picture will be drooling over your gorgeous friend, and what they missed out on will never escape their mind. This is especially important if the picture is of just you and one friend. A big group of bikini-clad ladies can be distracting and confusing enough to cause a reflexive swipe right, but with just two people in the picture, the attractiveness contrast becomes more stark. Crop that bitch out.

3) Protip: No guy really cares about silly adventurous photos, so if you’re sky diving, scuba diving, longboarding down a giant hill, or walking across a wooden rope bridge in the jungle, scrutinize that photo a little closer, because we don’t care what you’re doing, we care what you look like. That may seem harsh, but it’s true. Unless the ocean currents in your scuba diving photo are acting as nature’s greatest Instagram filter or the G-force velocity of your sky diving free-fall is making your tits look great, there’s no need to include these photos just for the sake of showing how adventurous you are. You can talk about all the fun exploits you’ve been on during the first date, but if you want someone to swipe right it’s about how attractive you are, not where you’ve been.

4) Here’s an easy one: If you’re wearing yoga pants, you can err on the side of keeping that photo in your roster. Pretty much every woman on the planet will look better in yoga pants, and whoever invented those deserves a Nobel Peace Prize.

5) Are you also doing yoga? Keep that one too. Bonus points if you’re standing on your head or doing some kind of backbend, because through extensive trial-and-error, women have figured out that certain yoga poses are consistently the most flattering. Men correlate yoga with sex. These photos should be utilized in virtually every social media app situation, usually as often as possible.

6) The above-the-head, angle-down-on-cleavage photo is the female equivalent of the shirtless bathroom selfie. This photo was popular when Myspace was the social media destination du jour, so it’s probably not the vibe you want to put out now. You will attract creeps, serial killers, dirtballs, and losers. Especially if you’re making a duck face. Men are creepy enough, threatening enough, and dangerous enough already – you don’t need to provoke them with a trashy photo. Best move is to avoid it.

7) If you have a picture with a child, please clarify whose child it is. It turns out that having baggage is not a good thing. We get that you love your kid, but before we can move forward, we need to actually know if that is your kid pictured.

8) Choose flattering moments. If you went to Vegas to party with your friends, the chances are that’s the sexiest you’ve ever been in your life. Everything is glossy and shiny, and men are idiots, so they are easily distracted by glossy and shiny things. If you have a photo of you and your friends wearing tight mini-skirts after two hours of hair and makeup posing in front of a fountain before waiting in line for two hours at some club that charges $16 per drink, use that picture. Pretty much any wedding photo is a solid choice, because the same Vegas principles apply. Chances are that is when you were looking your very best, and there is a difference between using a photo from Vegas or a wedding versus a photo from seven years ago when you were in college and didn’t have an ounce of fat on you. We know you look your best in these moments, and we are okay with it.

The About Me Section

The About Me section of your swipe-app profile boils down to one very simple concept: List everything awesome about yourself without sounding like an asshole. Forget about trying to tailor your About Me section to find your One True Love, because not only is this totally impossible, the swipe-apps are all about casting as wide a net as possible. The best you can do is approximate a somewhat neutral but personality-conveying paragraph and go from there. You might be thinking, “There’s nothing awesome about myself.” Well, you’re right. You’re a loser, and that’s why you’re on the swipe-apps in the first place. Just kidding. You’re a beautiful and special snowflake, and that fifth grade spelling bee championship you won in 1996 was a great accomplishment. You should be proud. Go ahead and ironically mention that to highlight your witty personality.

Listing all your greatest accomplishments without sounding like an asshole is easier said than done, both because people don’t like doing it and because it’s a tenuous balancing act to successfully pull off. I can understand why people don’t like bragging about themselves, because if you don’t feel a little uncomfortable bragging about yourself you’re probably an over-confident douchebag. Ignore that inclination. Without bragging, you risk your One True Love (or Potential Fuck Buddy) swiping left on you and swiping right on the douchebag that did brag about himself, and she will be lost forever. (Sidenote: If your résumé of awesome accomplishments is really so thin that you can’t come up with anything, delete all the swipe-apps from your phone – actually, throw your phone away – and go travel the world and have some experiences. For Fuck’s sake, get it together. Nothing wrong with a little self-actualization to jumpstart your dating career. Plus, you’re probably going to meet the love of your life on your travels, and you won’t need these stupid apps after all.)

When listing all your awesome accomplishments, start with the best, most general thing, such as your profession. If you’re a doctor, lawyer, dentist, or a Nobel Laureate, congratulations. List that first. If you have a stable job that suggests safety, security, and most importantly money, you have a pretty great chance of banging someone way more attractive than you. Remember the graph earlier in this chapter? Dancing around on a fancy yacht surrounded by half-naked models requires billions of dollars, but if you have a regular, boring, but lucrative profession, don’t despair, because all those years of being a tormented dork in high school had to pay off at some point, and that point is right now. This is especially true if you’re a man. While the group of attractive popular girls in high school that had sex with all the older jock assholes now have multiple kids from multiple fathers and nasty prescription pain killer addictions, you all of a sudden have status in society. And you’re making money. For any of those pretty, popular girls that turned out to be somewhat normal and are somehow still single, they probably don’t have lucrative professions, because they’ve relied on their looks their entire life. Now that these looks are fading, their attractiveness just aligned with your life circumstances, and you can catch that beautiful butterfly before she hits the last branch on her way down to the shit-smeared gutter.

I have nothing against someone who’s a garbage man, janitor, plumber, or sewage plant manager. These are probably noble professions, and I’m not judging you one bit for doing them. The reality is, however, that women do not think garbage men are sexy, because most women are superficial and want money. Same goes for creative careers like writer, actor, musician, or stand-up comic. I applaud your ambition, I hope you hit the big time, and please remember all the great advice I dispensed to you in this book so that I can be part of your entourage when you do your world tour. Unfortunately, being an unknown creative does not make you desirable on the swipe-apps. (And I’ll say it again here – especially if you’re a man – because if you’re a woman creative, you’re basically signaling that you think you should get paid for being attractive, and you’re okay that your fallback is to find an older, richer sugar daddy that can keep you from doing porn once you’re rejected from the 2000th audition.)

Another somewhat obvious protip for the About Me section is that you can’t go wrong with being funny. I’m about as funny as a pile of rocks, so I understand that this is easier said than done – some people just aren’t funny. My advice for you is this: When in doubt, plagiarize. Go on Netflix, watch one of the 70 comedy specials that are constantly crowding the queue and find something neutral, tasteful, and that you can meld seamlessly into conversation. Also, get a third-party opinion before committing to your material, because while you may think you’re funny or the mildly racist joke you heard isn’t that offensive, you’re probably not that funny, and the joke probably is that offensive.

Finally, avoid weird intense bullshit like political views or religion, unless you’re actually trying to find a life partner and you don’t want to waste time. But if you’re looking for a life partner, you should be on Match.com or eHarmony, not the swipe-apps. Basically, you’re in the wrong place.

My About Me Section

My About Me Section followed this formula: I included every single cool or interesting thing about me, stated like a résumé, and then add, “Not a great conveyor of personality using extremely limited characters. Probably should have had a friend write this. haha.” Now, that is really dorky, not very funny, and including the disingenuous ‘haha’ in written text is a pet peeve of mine, but it worked because it’s non-threatening, it showed I don’t take myself too seriously, and it dampens the doucheyness of listing literally every great thing I’ve ever done that a woman might like. Best of all, it was written by James, so I actually did have a friend write it. Here’s another example:

About Me

6’6” astronaut. MIT graduate. Former professional tennis player. Not a great conveyor of personality using extremely limited characters. Probably should have had a friend write this. haha.

Short and sweet. Perfect. I’m not an MIT graduate, I’m not an astronaut, and I never played at Roland Garros, but you get the point. You can always come up with two or three things about yourself, even if it’s that spelling bee championship win.

Here’s another example:

About Me

5’6” engineer. Scaled the Eiffel Tower. Once discovered a rare breed of water turtle. I am the 1996 Westside elementary school fifth grade spelling bee champion. Not a great conveyor of personality using extremely limited characters. Probably should have had a friend write this. Haha.

You’ll notice I’ve included height in each of those profiles. While not necessary, you should at least include a couple of photos that show your relative size compared to other people, because while women care about money and status, most also care about relative height. That is, they want someone taller than them. And not including height is subjecting you to the same problem of posting only the greatest photo of you ever taken, or only photos from five years ago – your date may take one look at you and want to immediately run for the hills.

I’m a fan of the above ‘About Me’ format because it tells people right up front that you’ve done some cool stuff, you have some accomplishments, and that you’re not an asshole about it. Again, all this advice is really tailored towards men, because when I read the two sentences women throw together on the swipe-apps, it was really just to filter out the total loonies. I swiped right based on attractiveness and the person being not totally crazy. Not because I’m entirely superficial, but because like everyone else in the world I’d rather have a conversation with someone in person before judging their character. (Don’t get me wrong, I’m mostly superficial, just not entirely superficial.)

Yet, I would be remiss if I did not point out some common mistakes that females make in their About Me sections, because I’ve seen a lot of female profiles, and many of the same turn-offs appear with staggering frequency. It’s one thing to be boring, stupid, or dull, and it’s another thing to be boring, stupid, dull, and common. Here are some tips:

1) When you write ‘not here for random hookup,’ no one is listening. Writing that is not going to prevent dudes from trying to fuck you very early on in the process. If it makes you feel better about yourself to make that extremely clear up front, then fine – be my guest – but I’m just telling you that that comment makes absolutely no difference to the male reader. More on that later.

2) Do you have wanderlust? Do you love to travel? Have you listed out all the places you’ve ever been to? Congratulations, you’re #basic. Nothing wrong with that, but you should be aware that you have just made yourself extremely generic and that four out of every five people that pop up on the screen are going to write the exact same thing. So well done you.

3) Are you into ‘Faith, Family, and Friends’? You’re also basic, but this might be good to include if you’re a Bible thumper who’s tired of shopping on ChristianMingle. It’s a good thing to announce that your special relationship with your Lord and Savior is the most important thing in your life. Yet, I would contend that you should probably be on Match.com, ChristianMingle, or eHarmony. If you’re into weeks of boring written correspondence and celibacy, the swipe-apps are the opposite of what you’re looking for.

4) A poetic, weird, rambling diatribe about life, mysticism, living in the moment, and chasing your dreams or whatever is overdone and really annoying. Don’t do it.

5) Don’t be a psychopath. This is the female version of ‘Don’t be a creep.’ Just don’t do it – whatever that means.

Remember, if you’re drop-dead gorgeous, none of these rules apply to you. You can be a crazy single mom who puts Jesus first, isn’t ‘here for a hookup,’ has wanderlust and believes that “If you can’t handle me at my worst, you don’t deserve me at my best.” Essentially, if you look like Blake Lively in that stupid shark movie every single dude is going to swipe right before reading your About Me bullshit.

Matching and Beyond

You may be disillusioned with the importance I’ve placed on women’s attractiveness or a man’s profession/wealth. Unfortunately, this is the new dating landscape, where everyone is reduced to 150 characters or less, a couple of pictures, and how versed they are in Snapchat captions and Instagram filters. Don’t despair, I’m disillusioned too. I wish my potential partner didn’t care so much about my job and I wish I didn’t care so much about her looks and her tits. But when Lucy and I broke up and I yearned to find someone new, that was the landscape I had to navigate. And so will you.

There’s a lot of steps between successfully matching with someone on a swipe-app and a penis eventually going into a vagina (which is what everyone is here for, right?), but it all starts with the profile (and really, by ‘profile’ I mean ‘picture’). It wasn’t just that I was a different person when I met Lucy, it was that I portrayed an entirely different person online. The best version of myself was the only way I was ever going to get laid again, so with a little help from Gay Friend James I created a new persona. What I didn’t realize until I was done with the swipe-apps was that I started to become the persona I created. I started to become an asshole.

I met Lucy that Halloween night in 2010 and I didn’t know what to do next. I was nervous, excited, optimistic, and eager. When I matched with girls online years later, I had to learn it all over again, except my hardened heart didn’t leave any room for those real emotions. My interactions with Lucy were like a jittery, bumbling Michael Cera character, while my interactions online were like a ’roided out Zac Efron frat boy. What is the best version of myself? Which version do I want to be? Before I knew the answer to either of those questions, I had to navigate What To Do Next. It’s a sobering thought to realize that nerves, panic, and hesitation are the hallmarks of love, while confidence, assurance, and disaffected indifference were the requirements for lust. I only wish women found the former more attractive.

Chapter Two



Part One: The First Date

A first date with someone in real life is basically like matching with someone online, because if someone swipes right you know they like you, and if someone is willing to go on a first date you also know they like you. And if you’re like me, in both instances the only thing left for you to do is to totally blow it. Fortunately, between jumping in Lucy’s cab Ted Bundy-style and refusing to eat her popcorn (is that a euphemism?), at some point that Halloween night I did manage to get her number. Waiting the obligatory two to three days before asking her out took every single ounce of willpower I had, because she was all I could think about. In class, my mind would wander to what it might be like to hold her, or fantasies of how we might spend time walking hand-in-hand along an empty beach… until my transfixed gaze would suddenly be interrupted by my Civil Procedure professor’s voice, cold-calling me to attention. At night I’d lay in bed and dream about what it would be like to share it with her, and I’d stare at my phone intermittently throughout the day, hoping she’d text, urging myself to resist the desire to send her a message, knowing I had to avoid appearing over-eager. I casually downplayed each mention of her name, because that’s what men do. Like when Jordan asked,

“What happened to that girl you left the party with?”

And I responded, “Oh, I don’t know. I got her number so we’ll see.” I tried to be Mr Indifference while I was panicking inside.

What I wanted to say was, I got her number!!! And I pray to God she’ll want to go out with me again!!! [_ What do you think Jordan??? Is she interested in me??? _]

When I finally did text her she seemed interested, and even though it was considered old school back in 2010, I even called her a couple of times. I can’t remember a single word of the text or those conversations because I was so nervous, but they must have gone all right because she agreed to go out with me again and we made plans for the next weekend.

I picked her up in my rusted snot-green Honda Accord and we went to a local pizza joint in Culver City. Within two seconds of her getting in my car, I could tell this might be something more than just a drunk make-out session at a law school party. She didn’t thumb her nose at my old and battered clunker of a car. She also agreed to go for pizza, which was a relief because I couldn’t afford a $200-a-plate dinner at the swankiest downtown restaurant that I wanted to take her to, and I appreciated that she didn’t expect or demand it.

We arrived at the order-at-the-counter pizza place and somehow I had the courage to make small talk. I can only attribute my ability to communicate with her to not really believing I had a chance in the first place. You see, there’s a certain level of confidence that every man must portray for a successful first date, and depending on the person, that portrayal comes from many different places. Let me give you two examples. The first from my friend Zach; the second from B-list celebrity Jason Sudeikis.

My Friend Zach

I know Zach from college, where I rode the bench on our basketball team and watched him lead us in practically every statistical category. I walked onto the basketball team because I thought it’d help me with the ladies, but it really just resulted in me watching a bunch of other dudes get a lot of attention at parties and subsequently fuck the hottest chicks in school. It also further engrained my small penis complex. Zach was the master of getting laid and was screwing so many women that his friends started floating the idea of an intervention. His promiscuity was especially baffling because for pretty much our entire college career, he was in a long-distance relationship with a woman who can only be described as The Perfect Catch. She was the kind of girl that rolled out of bed with no makeup on looking like she was in a Victoria’s Secret lingerie shoot. She was the hottest girl I’d seen in real life up until that moment – sandy blond hair with totally unblemished olive skin, a tiny cute nose, an incredibly curvaceous body, including perfectly shaped large C-cup tits, and to top it off she was smart, had the unique talent of actually having a phenomenal singing voice (and not just believing she did), and a great personality. She didn’t take herself too seriously; she was kind, gentle, and fun to be around. She also didn’t lord her attractiveness over everyone in that bitchy way that beautiful girls so often do, like every door must be held open and every drink must be bought. Why Zach did not treat her like the princess she was I will never know, and none of his friends could understand it either. He was constantly cheating on her with anything he could get his hands on.

Zach had the bad-ass swagger of someone who’d done significant jail time, and lived life like he was going to die tomorrow. One night we were out partying at the beach bars in San Diego when Jessica Alba showed up with two of her friends. They looked like they had been doing massive amounts of blow or were perhaps just riding high on Ms Alba’s recent stardom (this was before she became a totally irrelevant actor and enormously successful businessperson), but either way they were going big. The overflowing confidence of Ms Alba and company was seductive and alluring. She danced around that bar like there were cameras on her – doing spins, gyrating, moving however the music took her – completely immersed in herself and the mission of Having A Good Time. She was totally uncaring about anything outside the two-foot radius of cool that she emanated. To her, everyone else at the bar was irrelevant. The five guys in our group stood on the periphery of the dance floor, nervously captivated, amazed, and jealous at how confident and self-assured Jessica Alba and her friends were. Except Zach. Zach, who was at the time a seemingly average college student who didn’t have much going for him other than he was tall, athletic, and dating The Perfect Catch, walked right over to her and introduced himself. We couldn’t exactly make out how the exchange went down, but after Ms Alba said whatever she said, Zach spun on his heels and returned to us. When he arrived back at our group he said nothing, shrugged it off with a look that said ‘Her loss,’ and acted like nothing had happened. Just to have the balls to ask out someone that famous was impressive, and even though he got rejected, the look on his face made it seem like she was missing out.

True to form, 30 minutes later he was chatting with a smoking-hot blonde that made Jessica Alba look like Rosie O’Donnell, and at the end of the night he took her back to his apartment and fucked the shit out of her. That was Zach. It didn’t matter that he didn’t even register as the tiniest blip on Jessica Alba’s radar in the midst of what may or may not have been a cocaine-fueled bender, and it didn’t matter that he was unable to get her interest – it mattered that he believed he had a chance. Confidence is sexy, and Zach had it in spades.

While Zach was playing Russian roulette with his long-term relationship, there was some method to his madness for two reasons. First, he got laid by more gorgeous women than anyone I’ve ever met in my life. Second, if he was ever caught cheating or if suspicion threatened whatever relationship he might be in, he always had a fallback (or two). He never experienced loneliness or desperation about not being able to get laid, because there was always someone on the backburner. We all know a Zach. A guy with the je ne sais quoi confidence of someone that simply does not give one single fuck, and who will settle for nothing less than the prettiest girl in the room – which is the exact reason why the prettiest girl in the room wants to go home with him. I found it disheartening how many men I knew growing up who were just like Zach, who fed off the confidence of getting laid often by a lot of different beautiful women. Yet confidence begets more confidence, and bedding a seemingly limitless amount of women seemed to fuel having a never-ending supply of them. Women were drawn to him. It was like they could smell the sex on him, and they wanted a piece of it. I always thought getting the girl meant being a nice, sweet gentleman. Zach proved me wrong.

Jason Sudeikis

When B-list actor Jason Sudeikis first met his smoking-hot, soon-to-be fiancée, the somewhat famous actress Olivia Wilde, he was watching her dance by herself at a party. He walked up to her and said, “Whatever you’re looking for, you don’t need it,” and then immediately walked away. This cryptic, weirdo sentence could be interpreted in 10,000 different ways. Ms Wilde thought it was a reference to drugs, implying that he thought that she didn’t need drugs to have a good time. Turns out that’s not what he meant, but how the hell was she supposed to know? If someone said that to me, I’d roll my eyes and worry they might murder me in my sleep. But it was a genius move, because even if Mr Sudeikis really wanted Ms Wilde to go out with him, saying something obscure like that sends a message of indifference – like he doesn’t give a shit what she decides. Which makes her want him more. This was the first encounter Sudeikis and Wilde ever had, and it set the tone for their entire relationship. I’m sure there was some normalcy to their interactions later that evening, because he eventually got her number, and I highly doubt he accomplished that feat by saying weirdo shit to her over and over again.

The second time they hung out, Sudeikis didn’t show up with chocolates, roses, and a giant teddy bear, or do any of the things that people are traditionally supposed to do to successfully woo a mate. Instead, he kept her guessing and never gave her any indication that he was actually into her. He invited her to a sound check before one of his Saturday Night Live shows. (Which I guess is just as good if not way better than a giant teddy bear and chocolates, so maybe this is a shitty example, because no one reading this is going to have the opportunity to take their date to their Saturday Night Live sound check, but what they did on the date isn’t important – it’s what he said.) At one point during the sound check/show, she leaned over to him and told him it was the best date she’d ever been on. Instead of smiling like in a romantic comedy, he turned to her and said,

“Oh. This isn’t a date.”

She looked up at him and laughed, but he didn’t crack a smile. He was dead serious. When Ms Wilde recounted this story during an interview with Howard Stern, you could hear the excitement and confusion in her voice. She was nervous. The power dynamic was flipped, and she never knew where she stood with him. She couldn’t understand why she wasn’t being pursued, and his indifference never gave her that satisfaction. Now, they’re utterly smitten and deliriously inseparable and about to embark on something even more ill-advised than a love affair – they’re getting married, but apparently only when ‘weed is legal in every state of America.’ Now that’s romance.

I don’t know if Jason Sudeikis is actually super confident, if he was just portraying a superhuman level of confidence, or if he’s just a barking weirdo who smokes too much weed, but sometimes appearing confident just means landing somewhere between conversationally engaging and totally indifferent.

Back to the Date…

During that first date with Lucy, I did not have a half-dozen women on the backburner and I’m not a celebrity. Fortunately, there’s a third way that you can portray a high level of confidence – and that’s through despair and hopelessness.

I was more concerned with prematurely jizzing in my pants if she gave me a flirtatious smile than with portraying anything resembling confidence, as I was just trying to keep myself composed enough to not be laughed at. In anticipation of the date, I was my typical panicky, overly analytical, neurotic self. I had ten million thoughts racing through my head, and the perilous doomsday possibilities bounced around like pebbles in a laundromat dryer: What if I get something in my teeth? What if I order the wrong thing? What if she offers to pay? Do I let her? What if I’m boring? What if I order the wrong thing? What if I wear the wrong thing? What if my things are not nice enough? Should I buy nicer things? Was this date a terrible idea? Should I just call her and cancel…?

But then it hit me: I remembered I’d be a homeless law school dropout in a couple of months anyway, so who cares if my date with Lucy didn’t go well? I arrived at despair and hopelessness because I knew the impending doom of another failed attempt at love was inevitable. I wasn’t confident, but I came across as indifferent, and indifference is confidences’ often-mistaken-for first cousin. I paid for our pizzas and sat in the booth at the end of the restaurant. I relaxed and acted like I had nothing to lose, probably because I didn’t have anything to lose.

Under the cheap fluorescent lights of the Culver City pizza place, Lucy was even prettier now that she was sitting across from me. She wore a white tank top with a black and white shawl, and jeans. She was casual, but classy. She showed cleavage, but not so much it was distracting (well, it was a little distracting, but I liked that she didn’t totally rely on it). She wore almost no makeup and her face was still beautiful – the perfect Golden Ratio. She was the quiet, demur girl from Halloween, but as we made small talk I became more and more interested. We covered the basics. She went to college at Emory in Atlanta, and loved that city. She studied comparative literature and was top of her class. She loved to travel and she worked in Japan before coming to law school. She was from Long Island, and most of her family still lived on the East Coast. Her dad worked for Showtime Networks, and her mom didn’t work at all. She told me about her sisters. She loved dogs. She loved to read. She hated law school. The more she talked, the more entranced I was. A lot of people are quiet because they have nothing much to say, but not Lucy. She was smart, insightful, surprisingly funny, and didn’t take herself too seriously. She had an opinion on everything and anything, but not in a boorish way. The small talk we made wasn’t boring because there was an electric energy that fizzed and crackled between us. We could have been talking about the best varieties of peat moss to grow in your backyard and I would have still been spellbound.

There are certain girls that have been gawked at from the first time they sprouted breasts and they channel that power into being snotty, entitled, and rude, because in the end they’ll get whatever they want. These girls grow into high-maintenance, stuck-up bitches, and when their looks fade and the bitter resentment of the inevitable passage of time sets in, they become succubus life-killers, who realize that their best career choice is to pursue a lucrative divorce settlement by marrying a rich, shallow, lonely old man – preferably a doctor, movie producer, or tech mogul. These sorts of women have tragically underdeveloped personalities. They’re rarely smart, funny, interesting, or engaging, because they’ve never had to be. The coup de grâce of attractive females are the ones that don’t know it, and Lucy was one such creature. She worked for everything she’d earned in her life, and she had no idea what a beautiful, accomplished person she was.

We finished our pizza and I drove her back to her on-campus apartment. I parked out front and after a short pause and the exchanging of goodbyes, we kissed. There was another long, awkward silence where we both just sort of sat there in my snot-green Honda Accord looking at the dashboard. Then, in case I hadn’t already solidified my reputation as a potential serial killer, before I could stop myself I invited myself inside. I immediately regretted it, and became acutely self-aware at what a creepy move it was, but I was intoxicated with her and I didn’t want the night to end. She agreed, with the contingency that we wouldn’t be having any sex. Fine by me, as I was happy enough just to be in her company.

We had a couple glasses of wine and chatted some more. I gathered up the courage to kiss her again and as in all situations requiring forced sexual repression, each time the passion enflamed, I stopped just short of feeling like I was going to blow in my pants. Finally, we stripped down to our underwear, she loaned me a toothbrush, and we went through our respective bedtime routines for the first time together. Nothing could have been more intimate, and she must have thought I was insane. Here I was, a late-twenties man wanting to sleep at her house without being pushy about sex. I had created the paradox of being both a creep (by asking to stay over at her house) and a gentleman (by not even insinuating that sex was something I was interested in).

Just before I drifted off to sleep, my neuroses kicked in with a vengeance. There was something gnawing at my brain. If Lucy was okay with a neurotic weirdo like myself spending the night after two dates, how many random Zachs had she invited inside so they could pound the shit out of her with their giant horse-cocks? If I had been pushier about sex, would she have decided that she did in fact want to get laid? Was my cowardice ruining my chances with her? Was I predictably turning into the Nice Guy? I eventually I drifted off into a delightfully peaceful sleep and tried to ignore the fact that Lucy was probably eyeing me skeptically in the near-darkness, wondering to herself if I was going to wake in the middle of the night, chop her into little pieces, and then masturbate over her butchered corpse.

When I woke up the next morning I looked up at her popcorn ceiling, and smiled to myself, knowing life couldn’t get any better. The morning light started to naturally wake her and she stirred awake and said hello. I figured my imposition had run its course and I told her I would finally give her a break from me. When I got up and walked out of her place, I tucked my boner into my pants, choking it off at the waistline, and didn’t care that my balls were throbbing and that no amount of jerking off could ease the pain. I didn’t care that I didn’t get laid the night before and I didn’t know if I was in love, but I was happier than I’d ever been.

How to First Date

A good first date has the power to create momentum that can sustain a relationship for weeks. If lust is the urge of immediate attraction, infatuation is sustained lust, mixed in with a little friendship. The first date is the catalyst for all of this.

There’s not too much to say about a first date in real life, because it’s so much simpler than the swipe-app landscape. Whether you meet through a friend-of-a-friend, at work, church, or in a bar, there’s an immediate naturalness to those early exchanges when you meet someone in person. You know right away if it’s going to go well or bomb, and if it’s not natural there’s not going to be a second date, and it will be just awkward encounter between two strangers. With Lucy, I had the initial exchange out of the way and I had the third-party validation of a mutual friend – Hillary. That scenario makes things so much simpler than meeting someone in person, for the first time, after exchanging a few text messages on line and sharing basic biographical/geographical data.

Looming over any first date is of course the first kiss. Not having physically engaged with one another, you don’t know if kissing your date is going to be like tonguing a Great Dane, if their buck teeth are totally unavoidable and you’re going to bang your ivories together every time you go in for the kill, or if the kissing chemistry is indecipherably bad and no one knows what’s going wrong. Without getting that first kiss out of the way, sexual tension runs high, and there is at least some level of nervousness both neophytes share in wondering what it’s like to have each other’s tongues dancing around in each other’s mouths. Even if I’m a sloppy drunk mess when I kiss someone, if we decide to see each other again, breaking that physical boundary for the first time does wonders to decrease the level of awkwardness floating in the air. Kissing is the closest physical approximation humans have to determining whether they’d be good dance partners in life, and now that I’m a grizzled kissing veteran, in some ways I miss that nervous feeling right before a first kiss. The fact that Lucy and I already kissed took a lot of pressure off.

I’m convinced that my first date with Lucy went well because I channeled that hopelessness into indifference, but it’s an important reminder for any man who tends to get overexcited about first dates that, when in doubt, you need to care less. This advice falls into the category of Stupid Games You Have to Play to Get Someone to Like You, and it’s a close cousin to the Zach/Jason Sudeikis story: Years after that first date with Lucy, I went on a date with a woman who confided in me that what women really want is someone who makes them a little bit nervous – they want someone who is 80 percent nice, and 20 percent asshole. What she meant was, women want someone who is at least up to their standards, someone a little out of their league, and who will also keep them on their toes. My ‘nice guy’ persona represented safety and security, and therefore translated into boredom. Women want to experience the thrill of the chase, and being over-eager ruins this excitement for them. If women constantly think they might lose their man, it feels like an adventure. The same woman who dispensed this 80 percent nice/20 percent asshole advice then found out I was sleeping with other women. When she caught me texting some girl, she told me that she liked me because I was a ‘safe bet,’ and that she never thought I’d do something like that. She wanted me to make her feel nervous, but she also liked me because I was a safe bet. Well, which is it? This pretty much sums up women: Totally irrational in the most confounding, maddening, frustrating, ridiculous way. Apparently the 20 percent asshole portion should not be a part of you that wants to sleep with other women.

Getting initial physical intimacy out of the way, caring less, and being confident – each first date presents its own set of unique challenges. Dating and relationships are all about power, and prior to Lucy I always cared too much. I would overexpose myself and be way too transparent about how infatuated I was with my partner. I gave my potential future date all the power, and then resentment would build as I struggled to claw it back. Just like women want to feel nervous, men want to feel confident, and there’s a fine line between someone who makes you feel confident because they are constantly doting over you, and someone who dotes over you so much they have no sense of self and appear clingy. Men want to be assured that the person they’re with loves them more than anyone, but they don’t want a nut job.

The Right Timing

No factor is more important to a real-life dating situation than timing. Age comes in a close second. You might meet the love of your life right after they get out of a relationship or, even worse, right after they get into one. Or maybe you’re introduced through mutual friends during a phase when you’re going through a deep dark depression where you’re listening to a lot of Sigur Rós. Who knows, but timing can make or break every introduction in your life because both people have to be ready to meet someone for things to work. If you don’t have timing, you don’t have anything.

Age (sort of a sub-set of timing) is similarly important. Dating in your twenties is much easier than thirties and beyond because, in contrast to thirties and beyond, there are fewer expectations about money or status. People are less concerned about whether or not you’ll be able to pay a mortgage or afford college tuition for future children. In your twenties, everyone is just figuring it out, whereas once people hit 30, it’s all about what you do, what you drive, and how expensive the drinks are at your favorite happy hour spot. Status matters more, and there’s an expectation that by your thirties you’re going to have it figured out. If you’re a man and you take your date to a place where drinks are in the $5 to $10 range, you just drastically decreased your chances of getting laid. You’re also much more likely to be an asshole if you have money to spend, because everything you do will reek of entitlement, but you’re also more likely to get laid by the shallow women who chase after money, because if you take her to a $14 a drink place, the sex-vixen sitting across from you will have visions of drinking her $14 appletini while sitting poolside at your second home on the French Riviera.

I suppose I met Lucy at exactly the right time. I got away with being the overbearing Nice Guy because she was too stressed out and busy to deal with the 20 percent asshole that most women want. I’m sure if I met her a few years later she would have seen me for the poor loser I was, but at the time she didn’t. That first date gave me the momentum I needed. The only problem was the semester was ending, and ‘USC law student’ is a lot smoother introduction at cocktail parties than ‘homeless degenerate drifter.’

Part Two: On Matching, Messaging, and Meeting Up

The Internet dating world lags behind real life. When you meet someone in real life, you look at their face, they look at your face, and you guys might even open your mouths and start talking. That’s pretty much it. You’re done with introductions. Not so online. When you meet someone online, first you have to match, then you have to start messaging, then you have to get comfortable with the idea of actually exchanging phone numbers, then you have to get comfortable with the idea of actually texting that person, then, before the texting gets too crazy, you have to get comfortable with the idea of meeting them, then you finally meet up for a drink or coffee or some other very non-committal activity, and finally, once that process is complete, both parties can enter into the extremely awkward and fraught situation of speaking to one another for the first time in person. The Internet lags behind real life because there’s more steps in the process. It’s more complicated and much scarier.

If you’re a man, the immediacy of matching on the swipe-apps is way more efficient than your chances at a bar, which requires pin-balling around the room until some stuck-up bitch in a fancy dress is willing to drastically lower her standards to give you the time of day. Sadly, the right-swipe is not quite as good as your friend setting you up with someone, but at least it doesn’t require spending $20 a month for a Match.com account so you can send winky emojis and stupid pick-up lines back and forth to someone you’ll probably never meet.

If you’re a woman, dating on the swipe-apps means you’ll probably have to deal with an onslaught of inappropriately forward comments and dick pics from creeps, weirdos, and violent sexual predators. Just like Internet trolls posting in comment sections, some guys think that common decency doesn’t apply if you don’t have to face the person you’re speaking to. Thus, you might be terrorized with the inner thoughts of the most sexual frustrated degenerate males of society, which I’m told can be unsettling. To make matters worse, an outsized portion of attention goes to the most beautiful women, because men are delusional enough to think that being 40 pounds overweight and working at Chick-fil-A gives them a chance at dating Scarlett Johansson. And because rejection is impersonal, it’s easy for a man to right swipe or send a message to a woman way, way out of his league, because five minutes after hitting send, he’ll probably forget he even did that. This is why men engage in such ill-advised strategies such as Direct Messaging these super-attractive women on Facebook or Instagram without first matching on a swipe-app. Sorry fellas, but if she didn’t swipe right she’s not all of a sudden going to be wooed by your poetic virtual love letter that says something like ‘Nice boobs’ or ‘I want you to sit on my face.’ If you’re a woman who’s not blessed with the genetics to justify an entire Instagram feed of bikini shots, sadly Internet dating is an uphill battle.

Rejection and Commitment

Let’s say your Gay Friend James constructs a magic online profile for you, and you start matching with people. Dating is a numbers game, but dating on the Internet is especially a numbers game. No other time in history has it been easier to find someone who’s willing to go on a date with you, because wading through the numbers just got as simple as waving your index finger across a screen while you’re taking a shit, drunk at a bar, or lying wide-awake at midnight because you can’t sleep. The swipe-apps make this entire process super-efficient. They also make handling rejection easier and commitment way harder.

Rejection is easier on the ego because if someone doesn’t match with you, you’ll probably never remember it. They are a face on a screen, not a real person, and the pain of being told ‘no,’ whether through text or to your face, simply never happens. It’s the most anonymous form of rejection. If you do match with someone and they subsequently don’t communicate or suddenly go dark, there could be 50 million reasons why that happens. They could have deleted the app, there might be a glitch in the computer program, or they might have met someone. Regardless, staring at their profile or your string of unanswered messages to them will not help the situation. Always keep in mind there are other fish in the sea, and the swipe-apps just put the ocean at your fingertips.

Finding commitment is much harder because when you finally start ‘dating’ one of your matches, you’ll wonder if maybe you should have chosen the dozen other people you matched with on the app. After all, if you matched with them, there’s at least a possibility that you’re more compatible, right? Fear of Missing Out is especially prevalent in the social media age because we can be instantaneously jealous of our friend’s vacation in Bali or the free-spirited hippies doing mushrooms at Burning Man. FOMO can make you feel like everyone else is having all the fun while your life is passing you by. It’s also hard to make the initial commitment to go on a few dates, because if there are so many other options on your swipe-app, you don’t want to settle, and you don’t want to miss out. On the swipe-apps, judgment is passed swiftly, often based on an unflattering photo or a flippant comment in their bio – a quick un-match and you’re done with them forever. You don’t have to call them on a Bakelite rotary-dial telephone and give some speech about how you’re not ready for a relationship or worry about how it will affect affiliations with mutual friends. Commitment is much harder using the swipe-apps, and the people that move on with thoughtless expediency might end up missing out.


In the Fall of 2014, after Lucy had sucked the last drop of blood from my neck and drained me of all hope of getting her back, I would have gone down on Rosanne Barr while wearing a wig if she would have gone out with me. I would fuck anyone. The swipe-apps are the perfect vehicle for this kind of indiscriminate depravity, because in order to maximize the app’s benefit, you absolutely must lower your standards.

Most people using the swipe-apps have just graduated college, where everyone is beautiful, tanned, and super-fuckable. But don’t be fooled if you come across some super-fuckable hot woman and think you have a chance with her, because they are either on the app as a joke, as a game, or because they just got dumped by their boyfriend Neck Tattoo and they need to be reminded how pretty they are by matching with every single guy they swipe right on. These girls don’t need the swipe-apps. If they want to find a date, they just need to wear a low-cut shirt in any bar anywhere.

If you graduated from college single and unattached, you may be shocked at how frustrating, random, scary, and daunting dating as a young professional can be. Here’s the cold, hard truth: It seems that way because it is frustrating, random, scary, and daunting. If you took a job that transported you to a random city, broke up with your college sweetheart in your mid-twenties, or if you had no luck in college but have new-found confidence as an adult who’s started to make money, you might actually be on the swipe-apps to meet people. That’s a good start.

The threshold question on the swipe-apps isn’t, ‘Could I marry this person?’ It’s, ‘If I were semi-coherent in a really, really dark room, would I take my clothes off in front of them?’ That’s what you need to be asking yourself. The whole adage ‘when it rains it pours’ only works if you can get it to start raining, and sometimes the only way to get it to start raining is to fuck a woman named Martha who got fired from her Lane Bryant modeling job for putting on too many pounds.

Swipe-App Strategy

Some swipe-app daters will indiscriminately right swipe, collecting matches like a 1990’s eighth grader collects Pogs, and once they’ve amassed a sizeable collection they will determine which matches they want to talk to. There are actually computer programs that do this automatically, because apparently nerds have determined that the best way to find someone is to literally take anyone. This super-inefficient and annoying strategy puts you in the same category as the recently broken-hearted Hot Girl looking for an ego-boost, and if you do this you’re not only wasting people’s time, you’re giving them false hope. But I understand the allure – seeing all the people who think you’re attractive gives you a confidence boost, and finding the most obscure or interesting profile is a fun game – like people watching in an airport. I find that it’s best to be liberal with your right-swipes, perhaps making a snap judgment on the profile photograph and a quick glance at the About Me section – you’re lowering your standards without being overly scrutinizing.

Once you match with someone, the quicker you can engage in interesting conversation the better. Dispense with all bullshit. Don’t ask them how their weekend was, or what their favorite color is, what they like to do for fun, or how their day was. Messaging on the swipe-apps is a job interview, and you need to set yourself apart. Imagine the questions married couples of twenty years ask each other, and do the opposite of that. In other words, be interesting. Remember Jason Sudeikis? Tell them that whatever it is they’re looking for, they don’t need it. There’s no harm in having your opener be, ‘Wanna get a drink some time?’ because chances are you’re a busy young professional (or not-so-young professional) that doesn’t have time to waste. If being aggressive scares some people off, you’re better off without them. Exchanging text messages back and forth about how many nieces and nephews you have is getting you no closer to the ultimate goal of meeting up and knocking boots.

No matter how much Bumble founder Whitney Wolfe might disagree, as a man you have to be the aggressor. Many single women remain single because of how hesitant they are to put themselves out there, how indecisive they are once they do, and how picky they are once they find a good catch. These women will turn stale and desiccated before they realize they should have taken a couple more risks in their dating life, and possibly life in general.

I once matched on Tinder with a gorgeous sandy blonde hottie in her mid-twenties. We messaged back and forth for a couple weeks until I asked her if she wanted to get a drink sometime. She responded with this:

Her: Not until we chat some more and I feel more comfortable. That’s what the app is for, silly! (Winky face).

Red flags included her 1) calling me ‘silly,’ 2) using a winky face at the end of that message, and 3) using logic that made no sense. While I understand that some level of chitchat has to occur before a woman feels comfortable, an inordinate amount of this nonsense is why the old model of online dating has been replaced with the newer, more efficient version.

I thought about explaining to her that meeting someone off the swipe-apps is no more dangerous than meeting someone in public, say, at a bar or a random interaction on the street. In fact, it’s probably a lot safer, because you can at least start with some biographical data about them and ask a few preliminary questions, such as ‘do you have an extensive criminal history?’ or ‘have you ever butchered a date and ejaculated on the corpse?’ But meeting someone in person is really the best way to get to know them, and whether they approach you at a bar, hit on you in the gym, or you meet at a Taylor Swift concert, they are just as likely to steal your car/money/identity later, so there’s no sense in an idle text message exchange going on for weeks and weeks only to meet in person to find out they’ve used old pictures or had a tragic accident that’s left them hideously deformed. Relationships take time and effort to grow and develop, and that’s really not what the swipe-apps are for. The swipe-apps are for swift, efficient hookups. Where the relationship goes from there is up to you and your date. You’re not going to be able to determine if you really like someone by looking at a picture of them petting a giraffe on a safari they went on five years ago, so meet them in person. Of course I would still suggest that all women meet their first dates in a public place with a lot of other people around, because if your date gives you a vibe that they might have heads in their freezer, you can bail out immediately, but there is little risk in meeting up for a quick cocktail at happy hour or a Sunday morning coffee.

A Couple of Case Studies (or How to Spot a Prude)

The following are two situations where I matched, met up with the person relatively quickly, things quickly didn’t work out, and we parted ways. While pretty much unsuccessful in every respect, they are indicative of why meeting up quickly prevents wasting everyone’s time, why bailing out is easy when you have no stronger connection to someone other than a profile picture on a dating app or a contact in your phone, and why dating on the swipe-apps is a numbers game.

Case Study #1: The Haunted Doll House and Floral Print Sports Bra – Haley

Haley and I matched on Tinder. She was 28, slender, elegant, worked as a marketer for a shoe company, and had a snobby face like she was British royalty. Her photos included the standard dating app pics: A bridesmaid at a wedding. At a work event. Getting drinks with friends. Then, in her last picture, she threw a curveball. She was planking on her side in what looked like a children’s bedroom, using her free hand to take a picture of her reflection in the full-length closet mirror. She wore a floral print sports bra that was like a hideous wallpaper from the 1980s, with dark blue, pink, and green colors weaved together in what seemed to resemble rhododendrons (or some other fugly plant). It looked like someone had cut the neck and shoulders from a long sleeve T-shirt, slicing off the arms and mid-section to expose her belly, but leaving the extremely high T-shirt-like collar and thick shoulder straps. She slapped a sloppy child’s painting on her chest. I screenshotted the photo to my friend Will for further analysis and evaluation.

Yet she still looked pretty good, so I gave it a try. We messaged briefly and exchanged numbers. I was living in Tampa, Florida, at the time, and she lived about 40 minutes away closer to Orlando, so we decided on meeting halfway for a hike, which in Florida means meandering through a swamp dodging alligators. I was still new to the dating game at this point, so I figured that any girl that’s willing to get a little dirty and go on a hike for a first date must be pretty down to earth. I didn’t take into account the fact that hiking is not exactly an aphrodisiac.

Haley and I engaged in the usual small talk about our jobs, our families, and our lives, and the conversation was going so well that we didn’t want it to end, so we decided to get a quick bite to eat before parting ways. On the ride to the local pit stop, I realized I was drenched in sweat and my mouth was bone-dry. I was sure my breath smelled horrible after inhaling tiny insects and breathing the musty Florida air. We ate wings and each had a beer in the restaurant, and after I paid the bill I walked her to her car. I may have been a rookie at love, even after I lost Lucy, but I know enough to recognize that it’s important to make a move early. There is nothing worse than being friend-zoned in your twenties, so I moved in. We locked lips – or rather faces – in what felt like a messy teeth cleaning routine by an overzealous dentist. It was the worst first kiss ever. She opened her mouth too wide, or maybe I did, and at one point I felt like she was licking my face.

Not to be deterred, and wanting to give both her, and myself, a second chance, I arranged a second date. She’d offered to come to me, and after dinner we went back to my place. We sat on my $200 sofa I bought from some drifter off the Internet in my tiny little beach shack of an apartment, drank wine, and watched TV. She cuddled up next to me and we started making out, and soon our hands were exploring every square inch of each other and the breathing became heavy. She was hot. I asked her if she wanted to go into my bedroom. She nodded yes, and we made the ten-foot walk from the living room to my bed.

When hooking up with someone for a first time, the moments right after the decision to transition to the bedroom are always interesting. Are we going to have sex? Do I even like this person? Is she thinking these things too? She laid on the bed and I crawled next to her. We picked up right where we left off, and while I wish I could say the kissing got better, it really didn’t. Her tight body and my desperation to get laid were enough, however, and the blood rushing from my head into my dick made me hard as a crowbar. But when I went to unbutton her pants, she stopped me. I asked what was wrong. She hesitated. A long, awkward silence. Eventually she hummed out a protracted sigh, and said, “This is really fun, I just…”

I nodded in understanding and got up from the bed. Then, we had a brief, fumbling conversation where she tried to explain how she wanted to move slow, but couldn’t come out and say it. In fact, she would go ten or 15 seconds without saying anything. I could see the mental battle she was waging against herself in her head. I told her how I understood, how we could move however fast or slow she wanted, and how it was perfectly fine if we didn’t do anything more than just make out a little. She told me how bad she wanted to, she’d start to explain how important it was for her not to rush things, and repeated the same things over and over. Finally, given that it was late on a weeknight, she decided it was best to head home. I agreed.

Not more than 20 minutes passed after she left before she called me, explaining that she wanted to have a conversation about the risks and benefits of waiting for sex until marriage. I wasn’t demanding that we bang like rabbits, but I also wasn’t interested in having a debate about premarital sex, especially after the second date. Even as I was enduring this lecture in abstinence, I held out hope that if I made it through a couple more dates, Haley might see the virtues in having sex with me before standing at the altar. The more honest the conversation became, the more impatient I got. Finally, I told her it wasn’t going to work and that it was nice meeting her, and hung up.

On my way home from work one day, I recounted the story to Will over the phone. Will went to a small religious college where a lot of his classmates waited until marriage to have sex, and plenty of those marriages ended in heartbreak when the happy newlyweds realized they weren’t compatible in the sack. Haley was wrong, we agreed, and we separately re-examined the Floral Print Sports Bra photo to posthumously reflect on what could have been if she were not such a prude. As we did, Will realized something in the background of the photo. In the reflection of the closet mirror, just over Haley’s top shoulder, was a giant drab grey dollhouse that looked like something out of a Guillermo del Toro movie. High steeples capped medieval-looking towers; gargoyles perched on battlements, and giant wrought-iron gates stood imposingly at the entrance. There was no mistaking it – this was a haunted doll house, and my time with Haley forever became known as the Floral Print Sports Bra/Haunted Doll House situation.

Sometimes the red flags are so obvious that it’s your own fault for not seeing them, but little time or energy was lost with Haley because we got right to it.

Case Study #2: The Ballet Dancer – Brianna

There’s nothing wrong with living at home well into your twenties, and there are all kinds of reasons for doing this. Whether it’s to save money, get through school, or to help out your family, I’m not hating on anyone going down that route. If I could have tolerated my parents I probably would have done it myself, but if you find yourself in that situation be prepared to have it heavily affect your dating life, and find creative ways to work around it.

Brianna was a tall strawberry-blonde with long, toned legs and a perky, firm C-cup rack. I met her on Hinge, which marks the first time anyone ever met up in person after matching on that app. Hinge sucks open ass. I’m sure they’ll be out of business by the time you’re reading this book, mainly because they are so far from reaching a critical mass of people that it takes about three swipes before you’re out of options. But Brianna and I matched on Hinge, and the mutual friend that created the Hinge connection was not even someone Brianna or I were close to, which is just another data point for Hinge being a really stupid app idea. I don’t know why I have this irrationally strong hatred for Hinge, but I really do.

When I met Brianna I’d moved back to California from Florida, and she was from Orange County. Orange County is a lot like it’s portrayed in the TV show The O.C. It’s a new money version of L.A. with mini-mansions, perfectly manicured golf-courses, and more plastic surgery per square mile than possibly anywhere in the world. A lot of Hollywood actors buy fancy gated homes in ‘The Valley’ after a stint in rehab, a career lull, or early retirement. I imagine phone calls from money managers to B-list celebrities, advising them to scale down to a ‘modest’ two- or three-million-dollar home because they’ll never work again after picking up that transvestite on Santa Monica Boulevard. Brianna had nothing to do with the entertainment industry and was not famous, but living in Orange County meant that she came from a lot of money, and this was confirmed when I met her. When you come from money, your parents can afford for you to do unique and interesting activities, such as ballet.

Brianna and I had our first date at a local seafood restaurant, and she told me all about how after she graduated high school she forewent college and moved to Seattle to join a ballet company. I envisioned her making big bucks as a principle dancer for some touring company that performed to packed houses across Europe every night – sort of a Misty Copeland-type situation. Dancers are extremely athletic, have phenomenal bodies, and being associated with the theater at least puts you in contact with intelligent, successful people, so I was way into her. Turns out, it was not exactly a Misty Copland-type situation after all because Brianna basically had to pay to be a part of the ballet company (meaning her parents paid), danced for four or five years, and then came home to pursue the lucrative career of elementary school teacher (in other words, waiting for her very rich parents to die so she could inherit their millions).

But Brianna had a cool, bubbly personality and we seemed to have a connection. On our second date we watched a movie. There was tension in the air, but it definitely wasn’t sexual. When the movie was over, she inexplicably fled with a hasty goodbye. I was concerned and embarrassed, but even though she disappeared like she was running from a rapist we were still in contact, so I just avoided talking about it. I figured she had to take a shit or something.

Two dates and we’d barely grazed shoulders; I wasn’t sure where this was going. Then, on date three she told me about her religious awakening. She explained that she started going to church after a long hiatus and because she went through a ‘rough time.’ To me, a ‘rough time’ for a girl from the O.C. meant months of drug-fueled orgies, parties, more drugs, more degrading sex, more drugs, and a shit-ton of fun. I imagined this is what Brianna meant, and every successive time we hung out after that I couldn’t help but think that I’d just missed a great opportunity to have crazy sex with an athletic former ballet dancer. I figured if anything was going to happen with Brianna it was going to be holding hands while walking through the park after Sunday church service. Yet, just like with Floral Print Sports Bra, I persevered.

A week later we were planning our next date over the phone. I was half-checked out because of how slowly things were moving, and then she invited me over to her parents’ house to either bake cookies and/or watch another movie. What. The. Fuck. She wasn’t joking. She said it as though there was no third choice that didn’t involve something two normal adults might do, like go for drinks, or see some live music, or maybe have wild lusty sex together at my apartment. Just as with Floral Print Sports Bra, I held out hope for the remote chance I could exorcise some of her wilder pre-religious-awakening demons, and we would be sport-fucking in my tiny cramped apartment in no time. But this was the last straw. We stayed in touch but never solidified plans because it became clear that the only circumstances we would be hanging out involved cuddling with her family dogs on her parents’ couch under strict adult supervision. Like someone with horrible breath, she was oblivious as to why I was drifting away, and she continued to text me for weeks asking if I wanted to hang out. No thanks. I wasn’t interested in spending the three months at her house baking cookies and watching the Princess Bride on repeat before she finally touched my aching penis.

The point of these two case studies is that it’s not easy to spot a prude because it’s a conversation you can never have without sounding like an asshole, and it’s something unknowable until you’re actually about to fuck. So with both Brianna and Haley, I didn’t know it until we gave it a chance, and once I did, I got the hell out of there. Certainly being religious is probably a red flag, but it’s not absolute – I know plenty of gorgeous devote Christian females that wanted me to fuck them like meth-addicted hookers. Trust me. Keep reading.

From Messaging to Texting to Screwing

The disconnectedness of two people interacting on the Internet allows everyone to be hypercritical and brutal without feeling bad about it. It’s the same principle as when you’re driving and someone cuts you off. You flip them the bird, scream at them, make death threats, and say the most horrible things you’d ever say to another human being. You do this because your windows are rolled up and you don’t actually have to look at them in the eye while screaming bloody murder about reigning hellfire down on their immediate family members. The impersonality of hurting someone’s feelings takes the same form on the swipe-apps. All it takes is one swipe left or one ‘unmatch’ before you can just coldly and coolly disappear. It works both ways, and just as you can get a bad vibe from someone because they mentioned their love of Monster Truck rallies (and you hate Monster Truck rallies) or realize you swiped right by mistake on someone who’s transgender (and transgender folks are not currently your thing, but who knows what the future holds right?), the other party can do the same to you. People are ruthless and impatient on the swipe-apps, so there’s little margin for error, because one wrong text, one errant emoji, or one too many winky-fucking-faces, and you can lose the person on the other end forever. This is why, during the early stages of communication, you have to be your best and most charismatic self. If you had a particularly bad day at work and feel more like putting on shapeless clothes and Netflixing Bridget Jones’ Diary instead of chatting with another human, it’s probably best to respond to your most recent text messages when you’re in a better frame of mind. Whether you’re messaging or texting, pretend like you’ve just done a few lines of cocaine and say whatever it is that comes to mind. You don’t know who’s on the other end – their sense of humor, their tolerance for sarcasm, or their tastes and interests. Anything too bland and you commoditize yourself by appearing like every other dude she’s matched with. Anything overtly opinionated and you risk completely turning them off. If the strategy of pretending you’ve taken a few hits of cocaine doesn’t work for you, perhaps you should actually take a few hits of cocaine. Sometimes moderate drug use can be what you need to jumpstart your dating life.

There are hundreds of books written on how to win people over and get them to like you, and even books on how to pick up women, and these are all total bullshit. Unless the book is wildly entertaining on its own merit, it’s not worth your time because the thesis is always the same: ‘Be nice to people, but also be interesting.’ We’ve already been over this. If you’re too nice, you’re boring. You need a little edge. But you also can’t be a total dick, because if you’re too much of a dick no one is going to like you. There’s no magic formula for pleasing everyone, and it’s not worth trying to decipher why an Administrative Assistant named Sally who’s 43 miles away isn’t texting you back right now. She might be busy, she might have deleted the app, she might be using it as a confidence booster, and she might actually be a 62-year-old gay man named Jim who may or may not appear on an episode of MTV’s Catfish at some later date. At the end of the day, it doesn’t matter so much what you say; it matters how you react when you’re ghosted or flat-out rejected. Whatever it is you’re looking for – casual sex, a relationship, a life partner, or a drinking buddy – I promise there is someone out there looking for the exact same thing. Keep in mind that finding someone looking for the same type of relationship you are is different than finding ‘the one.’ The saying ‘There’s someone out there for everyone’ implies that your perfect person is out there somewhere. They aren’t, because that phrase is just some Disney bullshit that has been implanted in your head, and there are too many people in the world for you to have One Perfect Person. It’s a much better and more realistic strategy to just find someone good enough. Good enough is out there. I promise.

I’m an egomaniac with an inferiority complex, so I don’t take rejection very well. If a girl didn’t want to go out with me, I would wonder for weeks what I did wrong, or said wrong, and I’d go over a million different ways the situation could have played out where it didn’t ultimately end up with her rejecting me. Handling rejection well is an important attribute to have in all of life, but it’s absolutely essential for success on the swipe-apps. The strategy for what to say is less important than your reaction to what happens if things don’t go well. The second you get hung up on how someone responds to something you said, that’s when you’re dead in the water.

When I matched with someone on the swipe-apps, I would attempt to exchange phone numbers as soon as possible. If that person is serious about meeting up, they’ll be fine with doing this. If not, they either don’t have a basic understanding of technology or they have had multiple telephone-based stalkers, because exchanging phone numbers is not that big a deal. It’s not that hard to add someone to your spam numbers and delete them from your contacts list if they bother or bore you. People give out their phone numbers at bars when they’re so wasted they can barely see straight, so it should be way less intimidating to give out a phone number after matching on a swipe-app. You’re exchanging phone numbers, not social security details, and just because someone has your number it doesn’t mean they know where you live. If someone I matched with was unwilling to exchange numbers early in the process, I would unmatch them, not only because it was going nowhere, but also for fear of embarrassing myself by sending 14 ‘Hey’ messages in a row.

You never want your messaging inbox to look like this:

9:06 PM: Hey

10:15 PM: Hey.

10:23 PM: Hey!

11:40 PM: HELLo?

11:54 PM: HEy……

1:08 AM: Whatre u doing?

1:45 AM: Wanna come over l8r?

One ‘Hello’ or ‘Hey’ is enough. If they haven’t gotten back to you after that, they probably aren’t going to, unless it’s to notify you of a restraining order headed your way.

Final Thoughts

In order to find success on the swipe-apps, it matters immensely where you live. If you live in the boondocks, you might as well stop reading right now and hop on the next train to New York, Sydney, London, Port-au-Prince or whatever your closest big city is, because your dating pool sucks. Tinder, Bumble, Hinge, and the other swipe-apps are not exactly vibrant match-making tools in a place like my hometown of Redding, CA. You’re going stumble across the same people over and over, including all the bad first dates, friends of friends, and former elementary school bullies. Also, you’re probably on the swipe-apps in the first place because you didn’t find anyone in the pool of people you went to high school with.

The people I grew up with did one of two things: They either moved to the city or stayed home, and the people who stayed home all seemed to have the same career trajectory: They did drugs in their late teens, had babies in their early twenties, and now look like they’re 15 years older than they really are. If you live in the country and you’re hesitant to marry the girl you’ve been infatuated with since high school because you recently found out she let half the football team fuck her next to the tennis courts after school one day, you should probably move to the city.

After you’ve created the perfect profile (or Gay Friend James has done it for you), moved to the city, matched with people, and started chatting them up, you’re going to meet all kinds of folk. Everyone’s motivations for being on the swipe-apps range from trying to get laid to looking for a life partner, and there are all kinds of people, from upstanding citizens to human scum, strippers named Cindy to the girl next door. Meeting people off the swipe-apps is relationship roulette, whereas my relationship with Lucy was driven by a core of mutual trust and understanding. Our relationship endured because even when I did dumb or embarrassing shit, things worked because we gave each other a shot. We persevered through the awkwardness and uncertainty, and although I wish I could put a romantic gloss on why I fell madly in love with her, sometimes it just takes work and patience. Almost no one on the swipe-apps in interested in working or being patient, and strangers are understandably skeptical of each other. Cynicism is not a recipe for romance.

Chapter Three



Part One: Getting to Know Her

Uncertainty and Paranoia

The second of anything is hard to remember, and I’ve done enough binge drinking in my life to cause significant and possibly permanent brain damage, so I have no idea what I did on my second date with Lucy. It was 2010, so we texted a lot, but Lucy was not one of those millennials who’s constantly tethered to their phone. In contrast, I’m an obsessive-compulsive neurotic who freaks out when I don’t immediately see those little dots on my screen that indicate I’m getting a response. In the days and weeks that followed that first date, I’d pace around Jordan and Drew’s apartment after sending Lucy a text, staring at the blank screen, checking obsessively to see if she wrote me back, and would despair when I’d see that she hadn’t. I’d check after class. I’d check in the library. I’d check riding the bus home. No response, and I’d panic.

To cope, I did what any reasonable person would do in that situation: I flirted badly with other girls, jerked off a lot, and drank heavily. This pattern of behavior fell right into place with my self-destructive end of semester strategy of bombing my finals and leaving a burning trail of trash at USC before dropping out. Meanwhile, Lucy wasn’t ignoring me or intentionally not responding; she was just a well-adjusted human being that didn’t have to treat every pending text conversation as an emergency. Eventually she’d respond, and my nerves would be momentarily calmed.

When we did communicate, I would unintentionally do everything described in the other acclaimed book on dating, How to Ruin a Relationship Before it Even Gets Started (this is not a real book, although I’m thinking of writing it). For instance, I started calling Lucy the ‘Prettiest Girl of All Time’ to her face for fuck’s sake (!), after the character in David Foster Wallace’s Infinite Jest. We’d been on two dates and made out a couple of times, and here I was all but professing my enduring, bottomless love. There’s a fine line between a sweet sentiment and Ted Bundy-level psychotic. There’s a fine line between romantic and creepy, and I might as well have escorted her to the freezer where I was keeping my favorite dismembered body parts. Thank God she finally told me to stop calling her that, and didn’t hold it against me that I started doing it in the first place.

Lucy had a group of friends in L.A. that moved from back east to do what everyone does in L.A.: Write screenplays, get personal assistant jobs, make unjustifiably large salaries at tech firms, and post glossy photos of fun activities on Instagram. They would rack up $100 bar tabs at Taco Tuesday, Sunday Funday, and other stupid themed shitholes that rhymed with days of the week, and I panicked whenever she’d hang out with her male friends. I’d imagine worse case scenarios: A sleazy dude hitting on her, wooing her over with some extra-douchey pick-up line, wearing a very stylish outfit from J.Crew and smiling at her with his very smug, highly punchable face. Being the demure, kind person that she is, she would give him the benefit of the doubt and would just smile back and shrug it off, but he would wear her down, and just like she gave me a chance, she’d give him a chance too, and she’d realize what a loser I was, and she would be gone forever. She would see the truth – that J.Crew douche-bag was a stable, successful person, unlike me, and even though he’d have a highly punchable face and a stupid fucking name like Carter Wellington III or Chester Davidson Norris, she’d choose him over me.

I resented Lucy’s friends because the glossy Instagram photos of cocktails at downtown rooftop bars, or Mimosas in Venice, or comedy improv shows, or concerts at the Greek looked so fun.

There’s nothing like the smug confidence of a gay person who’s just come out of the closet, and a lot of Lucy’s friends had just come out of the closet after moving to L.A., and it didn’t matter that she told me most of her male friends were gay and that I shouldn’t feel threatened, I still despaired when she was in their company. They were confident, assured, and having the time of their lives. Meanwhile I was unsure of myself, had no confidence, and was having a quarter-life crisis. I tried to channel my inner Zach/Jason Sudeikis to play it cool; Make her want me, I’d tell myself, don’t worry if Lucy’s gay friends introduce her to their straight male-model friend. But I’d see her around law school and be hesitant and awkward. What did she want? Where was this going? What do we talk about? Law school classes? Our last date? When we’re going out next? Do we kiss? No. That’s silly. Too aggressive. Does she want that? Oh shit, late for class. Nice… er… talking?! And that’s would be it. See you next time!

Every moment of my life was a catastrophe, and I took pleasure in the catastrophizing of it.

The Horizon Doesn’t Look so Good

The law school semester was ending, and before I moved in with Jordan and Drew, I sold most of my belongings and crammed everything else I owned into the trunk of my old snot-green Honda. I knew I had to drop out of law school because I hated everything about it – the insufferable, smug students who would take extreme offense to the slightest micro-aggression, the indifference I felt towards the coursework, and my dwindling prospects for future employment, as mediocre grade after mediocre grade filled up my transcript – but despite my certainty at choosing a different path, the thought of driving back home and delivering the bad news to my parents was still a bit daunting. Armed with bitter regret for having chosen this so obviously wrong path, I’d imagine excitedly how in two weeks I’d be wandering the beach in the middle of the day, throwing pebbles into the ocean, content with no longer having to complete meaningless reading assignments or feel the pressure of being cold-called on some obscure legal administrivia. I would figure out my next move and have a chance to contemplate my life. Freedom. The sun would be setting over the Pacific, the Santa Monica beach would be deserted, and it’d be just me and some old couple walking hand-in-hand far off in the distance. I’d smile to myself while looking at the foam breaking on the shore. I’d look out at the vast blue ocean and a whale would breach over a cresting white-capped wave. Magic. The future before me with its endless promise. Adventure.

Except when I really thought about what that would look like: No money, no job, no prospects, and all my crap stuffed in my fucked car sitting next to an expired meter and a parking ticket on the windshield. In my mind I didn’t quite have the calm assurance that the movie-version of me had. I’d be grumpy, hungry, and tired as I plodded along the lonely beach. I’d walk back to my car, find the parking ticket, and go back to the beach, pouting and sulking while eyeing the old married couple with jealousy and hatred. I’d spike pebbles into the sand, watching them crater and bury. My mental state was less like the eternally optimistic protagonist in a love story and more like Michael Douglas in Falling Down. Already in a fragile mental state, if I lost Lucy after dropping out I’d end up wandering around Los Angeles from place to place and person to person, growing increasingly irrational and unhinged. I’d somehow come across automatic weapons, and the story would end with police shooting me dead as I brandished a love letter in one hand and an AK-47 in the other with a frantic, doomsday panic all over my face, right after exclaiming with my last breath that all wanted to do was to talk to my girlfriend ONE LAST TIME!!!

One Last Night

At law school in America (or at least California), ‘bar review’ is a weekly social event where a local bar or club offers drink specials that are far from special (e.g. $1 off bottom shelf liquor from 9:30 – 10:00 PM), and where all the law students try to drink themselves to death. Around midnight, a bunch of pale, bookish nerds reeking of cheap liquor would start to get kicked out. It was always quite a scene. There was one last bar review at the end of our finals weeks before the break, and Lucy and I had made plans to meet up. We’d only hung out another couple of times since that first date at the pizza parlor, and we still hadn’t had sex. I was under the assumption that it was rude to have sex with a girl too early, and I was trying to be a gentleman and get to know her first before climbing into her pants. So paranoid I was that my lackluster sexual performance would do me in with Lucy that one night, while we were hooking up, I actually refused to have sex with her. She was half-naked on top of me, I was shirtless underneath her, cupping her gorgeous, bare tits and choking off my raging boner in my pants, and she asked,

“Do you want to have sex?”

I thought this was a trick question, in that she didn’t really want to have sex, but figured I was getting impatient so was willing to do it if I really wanted to. Trying to emphasize my gentlemanly nature, and assuring her that I appreciated her for the person she was and not just because I wanted a piece of ass, I said,

“No, that’s okay.”

“Are you sure?”

No. I was not sure, and what she probably meant was I am horny and would like a dick inside me, even if it’s your tiny little pathetic wiener, so can we please fuck already?

I assured her that I was willing to wait, and that we could just go to sleep. Meanwhile, I’m sure she was rolling her eyes in frustration, confusion, and perhaps even a little anxiety that I might announce soon that I was gay and therefore wasn’t interested in fucking her at all. I was trying to be a gentleman, and I just hadn’t learned my lesson yet that that is the exact opposite of what you’re supposed to do.

Around the time of that last bar review before the first semester of my second year of law school came to a close (are you following?), our respective groups of law school friends didn’t know each other that well yet, so even though I would have preferred to take her as my date to the bar review like we were high school students at prom, even I knew that was a little intense. We agreed to meet there.

I was nervous and excited to see her, and I figured this was my chance to finally have sex with her, so during the pre-game at a friend’s house, I drank like the world was ending. A party bus picked us up and drove us to a club in Hollywood with a trendy one-word name, and when we boarded I realized this might end very quickly and possibly very badly for me.

When I sat down, I looked over at a smoking-hot Latina I’d never seen before wearing an impossibly short skirt that showed off her tanned and toned legs. Whether it was Lucy’s non-responsiveness, my own insecurity, or the fact that there was not enough blood in my alcohol stream, I turned into a drunken zombie and started flirting with her. I slurred a couple of lines, touched her leg, and she smiled back. Maybe this was my perception rather than reality, but I thought this might be my new girlfriend. A bottle of God-knows-what alcohol was being passed around, and I took a swig like I had a death wish as everyone cheered, like they were cheering for a Jackass character to jump out a three-story window.

The bus parked. I stumbled out and approached the black-shirted bouncer at the front door. He looked me up and down and immediately waved me back to the bus. I mumbled something about not being that drunk and stumbled back to the bus like an Irish dockworker. By this point, I could barely muster enough brain power to realize that getting turned away would mean I wouldn’t get to see Lucy, but when I sat down I managed to type out a confounding series of texts to her that led to a short and baffling conversation:

10:52 PM

Me: Haven’t ja seen my grocery store?

Her: ? Are you here?

Me: I captcha be there soon

Her: Are you ok?

Me: Ur pretty.

The now nearly empty bus bounced over L.A.’s pot-holed streets and I struggled to stay properly seated. My mouth hung open and I spat on the back of the seat in front of me a couple of times in the way that people with alcohol poisoning sometimes do. I remember thinking that throwing up would probably make me feel better, and I had no reservations about doing it there and then on the party bus our law school had rented, but I just dry-heaved a couple of times. When I was done I looked across my aisle at the totally sober couple sitting across from me, who had the startled look of people who were about to be mugged at knifepoint.

When we arrived back at the pick-up point, I was still far from Jordan and Drew’s house, and if I could have been left alone, there is little doubt I would have been mugged, raped, left for dead, and then arrested. A fellow passenger, some Blessed Angel of Mercy who wasn’t totally wasted, realized that I was in no shape to do anything for myself, and helped me call Drew. Not surprisingly, Drew didn’t go out that night, because he never went out ever. He preferred to stay home, get rip-roaring high, and play video games. Unfortunately on this night, he smoked himself into a weed-induced vegetative state, so the option of him picking me up was not available.

While I shouted nonsensical rants to passerby about politicians, law school, and pop culture, my Blessed Angel of Mercy formulated a plan. As I watched this blurry human figure tap out texts, make phone calls, and attempt to organize a way to get me home, I started to sway. I swayed to the one side, over-corrected to the other, saw the pavement rush up at me startlingly fast, and the then next thing I knew I woke up in my bed.

Drew would recount the details the next morning:

I was driven home by two law school classmates who had to carry me up the stairs of our apartment. They laid me on the living room floor and left, having had enough of my drunken nonsense, and Drew watched as I moaned like a woman on her period and shouted for ten or 15 minutes. Then, deeming it was bedtime, I slowly disrobed with the motor-coordination of a tranquilized zoo creature, wrestling with each item of clothing like it was an epic struggle. Once fully naked, Drew explained that I crawled and then lay sprawled out in the living room until finally I had the strength and coordination to make it to the shower. (Drew would look up at me periodically from his video game and laugh uncontrollably. There was some question about who was more out of it that night.) On my way to the bathroom I ping-ponged off a couple of walls, furniture, and other jagged corners, before I successfully made it. The shower ran for five minutes, then Drew heard me get in. Five more minutes later he heard a loud bang, and then a very loud muttering of “Oh no.”

Here is where Drew’s recounting and my memory somewhat linked up: The next morning, as Drew recounted these details to me, I remembered standing on the bathroom mat sopping wet, with my back to the bathroom mirror, twisting my body around and observing something wrong with my butt. It looked like I had a red mark on it, and that was the last thing I remembered.

Like a detective suddenly realizing the missing piece to the crime, I looked down at the pair of basketball shorts I was wearing. There was give in the elastic, but the fabric of the shorts were caked to the flesh of my ass with something sticky. I peeled the fabric of the shorts off the fat of my ass, revealing a thick line of dried blood on my right butt cheek running from my hip waistline all the way down and across the fat of my buttock, almost to my asshole. A pale, translucent patch of skin flapped loosely over the giant laceration.

“Guys,” I said to Jordan and Drew. “This isn’t good.” I showed them.

They let out Holy Shits! and Damns! and all the other exclamations of shock and we all looked at each other in horror. We walked to the bathroom. Blood was everywhere. On the walls. In the tub. On the mirror. It was like a murder scene. The thick soap holder that affixed to the tile wall had been shattered, and what remained attached was a sharp razor blade-like point of the fractured porcelain. Mystery solved. I drunkenly slipped in the shower, shattered the porcelain soap dish holder, and gave myself an enormous cut on my ass.

We decided it was probably best I go to the hospital. I grabbed my phone and keys and checked my phone on the way out the door. Lucy! She texted to see what had happened last night. Her plane left in two hours. She wanted to know if I was still taking her to the airport. I called and apologized, apologized some more, and then told her I was coming over. She said okay. The hospital could wait.

When I got to Lucy’s place, I was too embarrassed to even vaguely allude to the previous nights’ events, especially the giant laceration on my ass. Any stories of knife fights, dog bites, or other semi-heroic acts that could have led to such a bizarre injury were simply not ringing true. I certainly didn’t want to explain that I drank like the Tasmanian Devil and accidentally overdid it, but I had to say something, so I told her I drank too much and slightly overdid it. She was so sweet. Understanding. Patient. Kind. Non-judgmental. Beautiful. We kissed. I took off her shirt. Then her shorts. Then her underwear. I was rock hard, and I slid inside her. I almost blew right then and there, so I stopped.

“I have to stop.”


“I’m sorry. I’m just really turned on.”

How pathetic.

But it worked, and I somehow didn’t ejaculate in the first 15 seconds. We continued on in the quiet, careful, hesitant way that two teenagers both losing their virginity might have sex, and when I thought I was close to coming I told her to get on top. She did, I slide inside her once more, her pussy so tight and so wet clamping down on my cock, and she started grinding away. My right butt cheek started to sting, and I remembered the laceration that was probably flaying open like a knife blade had been run through a gutted fish. She thrust up and down, front and back, while all I could think about was the Manson family painting I was probably creating on her bed sheets. She worked herself into a fervor while I massaged her perfect, supple tits, and somehow, despite all my inadequacy and despite my distraction from my bleeding butt cheek, she came. Soon after I came too, and when she came out of the fog of orgasm and saw the weird look on my face, she asked what was going on.

“I sort of… um… something happened to my butt last night…”

Fearing her alternate interpretations, I clarified: “Not that,” and explained exactly what had happened. We rolled to the side and looked at the damage. She leaped off. I apologized over and over about the blood that was soaking into her sheets, which she didn’t even flinch at. Instead, she was worried and said I needed to go to the hospital. I was embarrassed and refused, telling her it wasn’t that big of deal. She insisted. Again, only worried about me. Finally, I acceded and told her I’d go right after dropping her at the airport.

All I could think about during the 15-minute drive was how I didn’t want to lose her. I needed her in my life and I wanted to make her happy. If she could accept me for my odd living arrangements, for getting too drunk, and for the gaping wound on my ass because I got way too wasted and slipped in the shower, she would accept me for dropping out and figuring out what I wanted to do with my life. I wanted to spend the holiday with her, not my family. I dropped her curbside and we kissed goodbye. She got out, I wished her a safe flight, and said we’d talk. I watched her walk away and hoped we would.

I never went to the hospital, and to this day, when I get naked for the first time with someone new and they ask about that scar on my butt, I have no plausible explanation other than the truth.

DtR, Driving Home and Dropping Out

Tread lightly when Defining the Relationship (DtR), because you might be forcing the other party into a position that they don’t want to take, and you might be irreversibly altering the balance of power. If you DtR and she says ‘yes,’ she wants a relationship, it might be only because you forced her hand. If she says ‘no,’ she doesn’t want a relationship, you might as well end things right then and there, because you obviously do want a relationship or you wouldn’t be asking, and she’s just shut you down. If you don’t ask at all, there’s a chance the person you’re sleeping with just wants a friends-with-benefits situation, and you’ll never know if they’re out there fucking a douchey guy that is more successful and better looking than you.

The day after I dropped Lucy at the airport, I packed up my car containing everything I owned, said goodbye to Jordan and Drew, and drove through the dry, desolate stretch of Interstate 5 that bisects central California. My mind wandered to Lucy. She was so patient, so non-judgmental, and so understanding, but that came across as indifferent – indifference towards me and our relationship.

How was she not mad that I drank too much?

Why wasn’t she angrier that I was unable to see her until the morning she left?

Did she care about us?

Why wasn’t she as infatuated as I was?

Was she going to call me?

Did she even care if I came back to school?

Finally passing the foothills of Sutter Buttes and up through the golden wheat fields that signify I was close to home, I took exit 677 off Interstate 5 for Redding and cruised down Cypress Avenue past the rows and rows of tract homes. I pulled up to my parents’ driveway in front of their cookie-cutter house and gave myself a mental pep talk.

I entered with three large duffel bags containing my life’s possessions in my hands, stood in the foyer, and said hello. My parents were in the kitchen chatting and cooking dinner. They turned, looked at me, then the duffel bags, then back at me.

“What’s going on?” my dad asked.

“I’m dropping out of law school.” Guilt overcame me when I saw their faces fall.

“…or I’d at least like to talk about it,” I added.

My mom started crying and my dad picked up the phone and started dialing.

“Who are you calling?” I asked.

“A family therapist,” he replied.

I took my things to the spare room and despaired. Later, my dad came in.

“Your mom is very concerned about your sister.”

“This has nothing to do with her.”

“She thinks she’s going to marry that Frenchman.”

“That has nothing to do with me.”

His face soured and he left. Talking with my father was always like we were sending telegrams from a great distance, or like we were speaking through a translator. Short, tense bursts of expressionless thoughts, with all the emotions bubbling under the surface. The next few days went on and on like that – an onslaught of guilt, with me doing everything I could to avoid them. Dropping out would be ‘too much for mom’ he explained, and it would be a selfish thing to do. “Law school is too much for me and I have no interest in it,” I would argue, like the spoiled brat I am.

The backstory is that after she graduated college, my sister saved up money so she could self-fund a missionary trip to France. It sounded more like a vacation than a crusade for the Lord, but she’s my sister so I tried to be supportive. My parents were worried, and after she stayed for a couple of years and loved it, they were even more worried she was going to make a life there, not to mention the fact that a lifetime missionary is not a necessarily a promising career path. My parents, like most parents, are pragmatists who wanted a stable and happy life for their children. The fact that I was getting a law degree from USC was a panacea. Not anymore.

Sitting in the therapists’ office on Christmas Eve, I just wanted the whole thing to be over. I wanted to be back in sweatpants, stuffing my face with Christmas sugar cookies. Practically before the tweed vest-wearing, bespectacled therapist even opened his mouth, I was already exclaiming that it was ridiculous we were even there, and I assured my parents I’d go back to school. This is how my family accomplishes everything: Passive aggression; masking a personal problem with a familial one; and a large helping of unrestrained guilt. My parents had won. I agreed with everything everyone said and counted down the minutes until we got home. In retrospect, I probably should have ignored my parents’ concerns and dropped out anyway, but the prospect of returning to Lucy as a law school failure worried me. I wanted to be legitimate for her, I felt bad for my parents, and I realized I was halfway done with school, so I committed to going back and finishing.

The rest of the holiday was dull. I paced around the house waiting for Lucy to call and avoided interactions with my parents. When Lucy and I finally did speak, she seemed a million miles away. Dogs would be barking in the background. Her mom would shout something at her and suddenly she’d be on a distracted errand. She’d come back on the line. ‘Yes? Can I help you?’ I could almost hear her say, and would have to repeat myself.

Between the two family dogs, her sister’s four-year-old son, and the New York habit of shouting through walls when they needed to get someone’s attention, it sounded like Christmas at Lucy’s house. The cold New England weather, the decorations, the rich neighbors with the former head fund manager patriarch stopping by to visit, the chaos of last minute shopping, the hustle and bustle of everyone vacillating between festive and moody – these things seemed like Christmas. It was the opposite to brooding around a small two-bedroom home in a quiet farm town with your parents who are passive-aggressively running your life because you have no balls. My parent’s house was as dull as a museum and as quiet as a morgue. Plus, my sister was spending Christmas in Paris, which only made it worse. With her around, at least we could have fought about politics or religion or something. That was one lonely holiday that I marked as just another failure in the disastrous string of calamities that my life had become. I couldn’t even drop out of law school properly. Most of all, I missed Lucy.

Meet the Parents (and Other Less-than-Admirable Family Members)

Whatever paranoia, nervous anticipation, and concern I had about my relationship with Lucy was alleviated once I returned to school. Her assurance in person that she was happy I didn’t drop out and wanted to be with me did wonders for my confidence, and we fell into a familiar routine of law school classes, papers, parties on the weekends, cooking dinner together, and making love. Soon, the semester was over and we had to determine our summer plans. I worried she might flee east, and was relieved when we both stayed in L.A.

Despite going back to school, my disillusionment with law school hadn’t faded, so I half-assedly took a job writing the statement of facts sections for an appellate public defender, which is as boring and mind-numbing a task as it sounds. The only thing keeping my eyelids from drooping were the gruesome factual scenarios of the cases we took on – a garden variety gang murder here, a child molestation case there, and whether it was a 13-year-old shooting a fellow teenager because he was wearing the wrong shirt or a middle-aged man trying to stick his penis into a confused toddler, the job seemed perfectly suited for my personality: Bitter, cynical, disgusted disappointment with the world. While I poured over revolting trial transcripts of Los Angeles County’s most troubling cases, Lucy got paid to do research on Intellectual Property law for one of her professors. We’d study in the morning, break up the day with a lunchtime workout, and finish the afternoon of graft before going home and making love.

The getting-to-know you phase happens quickly when you fall into a routine, and in our hours together, I started to learn about Lucy’s family, like how her older sister Sarah had an out of wedlock child named Jax. Fine. No judgment there. But as Lucy explained it, Sarah gave birth to Jax without the father’s knowledge in her final year of college and had no intention of ever telling him he had a kid. I also saw nothing wrong with that, so long as Jax’s dad was incarcerated, a serial killer, or if Sarah was the victim of rape. No such case. He had a stable job as an accountant, no criminal record, and no other baggage to speak of. Lucy would tell me that Sarah did this because Jax’s dad was obsessive and controlling, in the same way women won’t date a man because he’s ‘a creep,’ even though that could mean anything. Being obsessive and controlling is a problem in a relationship, but it shouldn’t disqualify you from being a father to your kid. Sarah’s fling wasn’t even a one-night stand, which would still be a bad excuse for not telling someone they have a child, so what the fuck Lucy?

Lucy deferred, said it was complicated, and I could tell she didn’t want to talk about it. I quietly seethed, thinking we all have our problems, but how did the entire family turn a blind eye to how fucked up this situation was? Whatever cynicism I had about love and relationships only got worse. If you’re willing to let someone blow their load inside you on more than one occasion, you should be obligated to tell them when biology takes its course and nine months later a baby pops out. At least let the poor schmuck know.

The backdrop to all this info was that Sarah was getting married that summer, and like getting the scouting report for the opposing team, Lucy divulged more info on her family in anticipation of the wedding. Her parents lived in an old Long Island mansion, but her father Patrick commuted to New York City during the week where he worked as an executive at Showtime Networks. Lucy’s mother Millie stayed behind to walk the dogs, fret over home renovations, write to family and friends, and pen complaint letters to service providers she felt aggrieved by. During the week Patrick would stay with his mother in a brownstone apartment in Manhattan. A WASPy, blue-blood Long Island family through and through, Lucy’s great grandfather served in L.B.J.’s Presidential cabinet.

Then came the dull but inevitable suburban details, like how Patrick had an affair many years ago with their Long Island neighbor. As if my parent’s history wasn’t enough, it was disheartening to learn that not only did Patrick have an affair, he did it in the most nonsensical and obvious way possible. Despite living in Manhattan during the week, giving him infinite opportunity to secretly bang every secretary or cocktail waitress he came across, he chose to sleep with a neighbor a few blocks away from his bored, lonely, stay-at-home wife. I suppose this should be anticipated, given that people are fucking idiots, and they are at the height of their idiocracy when engaging in reckless behavior like having an affair, but it made even more sense when I first met Patrick that summer – he was a goon; a pampered, poorly adjusted East Coast prep school kid whose parent’s almost certainly dressed him in cashmere sweaters and Dockers from the time he could walk. I could picture a young Patrick, on the slopes of the French Alps with a private skiing instructor, whining that his feet hurt, and then sitting inside the lodge all day drinking hot chocolate and being pampered in the special, attentive way that only the super-rich are. He was the kind of child that turns into an emotionally stunted, immature adult. Hearing of Patrick’s infidelity, I looked inward, at Lucy and I. Was cheating a mistake I was destined to repeat? Was Lucy going to cheat on me? First my parents, then my father, and now Lucy’s father. It seemed like every marriage of more than a few years had been fractured by someone straying. I fretted, and my insecurities deepened.

Then I met Millie, and it was hard to blame Patrick for what he’d done. She was a matronly woman who’d let herself go, wearing the same floppy sweatpants and sweatshirts every day, her hair always looked like it hadn’t been washed in months. She was a busybody, filling her daily schedule with neurotically fussing over her two dogs, home repairs, and tedious gossip about other families at the beach club. When she discovered Patrick’s infidelity, like many middle-aged housewives who have let themselves get fat and unattractive and don’t want to be alone, she swallowed her pride, forgave him, and stayed.

The Love Triangle of the Newly Betrothed

Standing on a gravelly road outside a Long Island beach club with a bunch of bridesmaids, waiting to be picked up for the ceremony, Lucy pulled me aside.

“I forgot to tell you something. It’s kind of important,” she said, and then explained that Sarah was still in love with her future husband’s best friend. Sarah, about to marry the man she’d been with for two years and who’d become the surrogate father to Jax (a child kept secret to his real father), was still in love with that man’s best friend. I think it would be impolite to not point out what a toxic cunt this woman was. You see, after she was impregnated by The Mystery Accountant in her last year of college, she fled home to be pregnant/sulk for nine months. Shortly after the birth she moved to Hawaii to sow more wild oats (because apparently the oats had not been sowed enough by young motherhood with a dude she didn’t really like). The next four years she partied, maintained a meticulously perfect beach tan, and had flings with gorgeous accented foreigners. She was the cool, hot mom with a toddler in tow. While young single mothers across the globe struggle to make ends meet, Sarah lived off her parents and family friends and had the time of her life. She had a short, intense love affair with a rugged Australian surfer named Quinten, complete with impeccable tan and thick Australian accent. He was the quintessential heartthrob that every American woman in their twenties dreams about dating – foreign, with curly locks, always the scruffy five-o-clock stubble, and a fantastically fit body yet to be worn down by the grind of a desk job, or indeed any job. He was the foreign version of the tattooed, adventure-sports loving bad boy that women lust over; the ‘cool dude’ who treated his twenties like it’s the only decade he has left to live; the kind of guy whose future wife goes from passionately in love with her Australian hottie to cold regret when she realizes she banked the rest of her life on a handsome surfer with no career prospects. Slowly, the Coronas catch up to him, he develops a potbelly, and when it’s time to start a family there’s a purchase of a modest suburban home 600 miles from the beach, and it doesn’t take long before the mortgage payments can’t be met, his looks start to really fade, and the possibilities are no longer infinite. Then the fighting begins.

But at the time, it’s great – Sarah dodged that bullet by never committing in the first place. Instead, while Quinten and Sarah were having passionate, youthful sex in their beach shack in Hawaii with their gorgeous, tanned bodies nightly intertwined, Quinten’s best friend Denny laid in wait, knowing that nothing with Quinten was built to last. Denny knew that in life and in love, timing is everything, and he just needed to be there to catch Sarah on the way down, once she woke up and realized what the next 30 years with Quinten would look like. When she did, Denny wore her down with kindness, love, affection, and attention. He knew that with Sarah he was overachieving in the looks department, but as you already know, for most guys that’s all that matters. She relented. So there I was in Long Island, waiting for a car to take us to the venue to watch them get married, where Quinten would be watching from the gallery with the vacuous, empty look on his face that is stupidity but is sometimes mistaken for assurance.

The wedding was held at a very ritzy and exclusive beach house in the Hamptons. With Lucy engaged with bridal party activities, I floated around and answered the standard small talk questions from wedding-goers I’d just been introduced to. While I chatted about where I was from and what I wanted to do with my life after law school, I noticed a stylish grey-haired man with a large nose and a camera around his neck – the wedding photographer. He made his way around to a room in the back of the house, where Lucy was slipping out of her casual clothes and into her bridesmaids’ dress, with the rest of the bridal party. It would be days later before I saw the half-naked photos of Lucy. As my blood boiled I remembered watching the photographer meander around with the lonely hope that life still had some excitement left to offer, even if it was simply photographing young women in their underwear. I felt sorry for him, mainly because the look on his face seemed all too familiar: Quiet desperation.

Was this where I was headed?

At the reception we all mingled at the beach bar. The newly betrothed acted like complete strangers, probably because the bride was preoccupied. We stood around watching Sarah and Quinten talk to each other like nervous teenagers, and everyone thought the same thing: They’ve been talking for a long time. Too long. I waited for them to sneak off down to the beach for one last rendezvous, and it got especially weird when at the end of the night Denny walked up to Sarah while she was mid-conversation with Quinten and told her to come to bed. A whispered argument ensued, Sarah refused to leave, Denny pleaded with her, and Quinten stood silently by, clueless, as though he was a completely innocent party to this mess. Denny stormed off, and we all continued to cast sideways glances at Sarah, who was still talking to Quinten, wondering why she thought this was okay.

It was around two in the morning when I found myself sitting in Patrick and Millie’s living room watching Patrick pour everyone a nightcap. Around the living room couches sat Denny, Lucy, Patrick, Millie, and, inexplicably, Quinten. Here was Denny with no Sarah, and right next to Denny was Quinten. I was pretty drunk and tired by this point from putting on a good face with Lucy’s family, but I watched Patrick and Millie chatting happily, and Denny hamming it up with Quinten. I looked at Lucy like ‘what in the fuck is going on here? Where is your sister?’

Apparently she missed the message, because she just looked at me and smiled.

Getting to Know Her

I suppose I should stop saying ‘no judgment’ and then proceed to judge the shit out of everyone and everything. It’s like when people say, ‘With all due respect…’ or ‘no offense, but…’ and then say something irreversibly egregious. I realize I’m probably losing credibility. But you can’t choose your family, so despite the weirdness of Sarah’s wedding night, I thought the visit to Long Island was a success. Meeting the parents went all right. If anything, I was even more interested in Lucy, because she was the quiet, shy, intelligent, introspective, Black Sheep enigma in a family stuffed full of lunatics. Being thrust into the world of East Coast privilege, with the parties in the Hamptons, the hedge fund manager neighbors, and fancy beach clubs, was all right with me. It was a million miles from the back-country farm folk I grew up with in Northern California. They just seemed more miserable and with less money.

Getting close enough with someone so that you know intimate details about their family takes time, but by the end of the summer Lucy and I were best friends, and I was happy. When she shared things about Sarah, or Patrick, or anyone from her family, I wanted to feel comfortable in her confiding in me. Sometimes, that meant not telling her how I really felt. It was August of 2011 when I started my third year of law school and I thought there was almost nothing I couldn’t tell Lucy, and I hoped she felt the same.

Graduation loomed on the horizon, and I had no idea what I wanted to do with my life, but it turns out the career prospects for a mediocre law student with tepid passion for being a lawyer were not great, and it didn’t help that the legal job market wasn’t exactly thriving at that time. I was living in the moment because I had Lucy, and perhaps too much so.

Did my life revolve around her too much?

But she was my best friend, so isn’t that how it’s supposed to work?

Part Two: The Women of the Swipe-apps

Let’s start with a simple reminder for all the men out there that hotness and craziness are pretty much directly related, and this is something to keep at the forefront of your mind at all times. In this section, we’re going to get into specific kinds of daters, but I don’t want you taking your eye off the ball. There are excellent, google-able version of the hotness/craziness correlation all over the Internet, but suffice it to say, keeping this steadfast principle in mind throughout your dating life will help you tremendously.

There’s a lot of female online swipe-app daters out there, and I know because I’ve met just about every last one of them. Sadly, the snap judgments you might make based on an online profile are often staggeringly true. While I can feel the collective hate-glare from everyone accusing me of prejudice, I’m sorry I’m not sorry – it’s true. Stereotypes exist for a reason. Getting to know Lucy was about learning her idiosyncrasies, her likes and dislikes, and all her funny tendencies. On the swipe-apps, nobody has time for that tedious shit. The swipe-apps are about efficiency and speed, and if the fundamental core of what someone is about can be boiled down to a few pictures on a swipe-app profile and a short About Me section, it’s helpful to have some shorthand references. The more swiping you do, and the more first dates that you go on, the more you realize that everyone starts to look the same – people become caricatures of their online profiles. I know we’re all a unique and beautiful snowflake, but if someone is a self-described ‘free spirit’ who’s on a tropical island in a bathing suit, has a bunch of henna tattoos and wears bracelets, you’re getting a specific type of person; and if someone is a cardigan-wearing doctor whose profile pic has them arm-in-arm with their mother while wearing matching sweaters on the Champs Élysées, you’re getting a very different type of person. Immediately appreciating that difference is important, because otherwise a few weeks into the relationship you’ll be lying on your back wide-awake at midnight, praying for some sleep, while the free spirit blasts Cat Stevens and dances around the kitchen. Or you’ll be paragliding on a tropical vacation with a joint in your hand while the doctor reads the Economist under a beach umbrella with SPF 250 sunscreen applied all over her body. On the swipe-apps, it’s helpful to know up front whom you are dealing with. Here’s an overview of what’s out there.

Single Mothers

I can’t imagine how difficult it is to be a single mom (unless you’re Sarah, of course – in that case you just gallivant off to Hawaii and ask your parents for monthly checks). The Young Single Mother profile can be especially tragic, and will usually contain the same generic likes and dislikes as any other profile, and then include something like this, typically with misspellings, weird abbreviations, grammatical mistakes, and ill-conceived logic:

Mother of 2 girls – they r my world!, or:

Busy mother of 8 yr old boy. He is my everything!, or:

Happily divorced single parent of the cutest boy everrr! HE COMES FIRST!

Here is the About Me section from an actual real-life profile I just matched with as I was actually real-life writing this:

I am a single mom of a handsome little boy who is the center of my universe. My son is my number one and the most important part of my life. I’m a very laid back, go-with-the-flow kinda person and I am looking for someone who is the same.

Let’s break down that one down.

First of all, your child better be the single most important part of your life, because by definition children are helpless mewling cretins, and it is your responsibility as a parent to take care of them. If your child was anything but the center of your universe, you’d be a selfish idiot.

Second, if you say your little boy is ‘the center of your universe,’ you don’t need to directly follow it up with the fact that he’s ‘the most important part of your life.’ We got it the first time, thanks.

Finally, it’s admirable that you’re trying to make being a single mother ‘no big deal’ by throwing in how chill you are, but you’re still a single parent – you should have your shit together and you’d probably be better off as an uptight maniac who does everything with military precision. The ‘very laid back, go-with-the-flow’ side of you was the person you were when you had sex without using any birth control and then said “fuck it, I’ll just go ahead and have this baby.” That person is going to produce another person that’s just like you, and the vicious cycle is going to continue, so maybe you should think about changing your ways. No offense, just saying.

And no one cares if your son is ‘your world’ or ‘your everything’ or how much you love him. I would hope your son is your world, because that’s how parenting usually works. Also, when you say those things, it’s very transparent what a desperate cry for help it is. I’m sorry that your circumstances have resulted in you having a child with an absentee and/or fuckwit father. That is a difficult situation, and you are strong for enduring it (although possibly stupid for letting it happen in the first place), but let’s not get carried away with telling everyone how happy you are, because we know you’re lying. You’re not fooling anyone.

I don’t mean to be negative, because there are some huge advantages to dating a Single Mother. First of all, you know they’re down to fuck, because they have a child. That’s important, because we’re trying to get everyone laid here. Be safe though, because their track record suggests they’re not exactly the most responsible of daters. Second, single moms are pressed for time, so if they’re into you they’re probably not going to waste time getting right to it. Their responsibilities as a parent limit their interactions with the opposite sex, so you don’t have to be concerned about them reading you Bible verses by candlelight or watching the Princess Bride on repeat at her parent’s house. They won’t waste your time. Finally, be aware that they might be looking for a stand-in father, and unless you’re a total moron and that’s something you’re into, don’t get trapped by that.

No man looks at a single mother as a boon to a dating situation. There are many reasons for this:

1) A vagina with labial walls that flap outward like the pink wings of an angry bat is not attractive.

2) Sexual encounters interrupted by a little bastard knocking on the door and complaining about monsters under his/her bed.

3) Cancelled dates when a babysitter cannot be procured.

4) Biological dad, if he’s still in the picture.

5) A vaginal birth means a human head came out of there, which means she will never be the same, ever. This is especially important for guys like me, although possibly irrelevant if you’re hung like Ron Jeremy.

As with any red flag, the presence of a child in a woman’s life is immaterial if she’s a total smoke-show who’s hotter than the blazing pits of hell. Attractiveness trumps all (in the short term). Yet, the single mother is among the most extreme of compromises, and I will almost always run for the hills once I see that a tiny humanoid is involved.

Case Study #3: Leslie

When I swiped right on Leslie, the wound of losing Lucy was fresh and I was living in Tampa, Florida. She was three years younger than me with short blond hair, a sweet, innocent face, and beautiful green eyes. She looked like a bleached-blonde Scarlett Johansson and was a lot hotter than me, but I was a single lawyer and she had two kids from her very brief failed marriage, so her life circumstances had aligned with my looks. I had to take advantage. Things were just starting to heat up for me on the swipe-apps, and I was having a lot of conversations with a lot of different women, which is problematic for any first date situation, because you end up asking how their equestrian event was, only to realize they have a paralyzing fear of horses. I wasn’t sure what ground Leslie and I had already covered, so after messaging back and forth for what seemed like an eternity, I had a lot of pre-date research to go over to make sure I didn’t put my foot in my mouth.

Sometimes the biographical history of the women I dated was just as important to me as trying to get in their pants, and Leslie’s backstory of how she became a smoking-hot divorcée with two kids at the ripe old age of 25 was no exception. She met her husband at 16 while rebelliously bar-hopping in a mini-skirt with a fake ID. Her husband, nine years older and Special Forces in the military, was not deterred at all by the fact that she was an impressionable minor or that fucking her was illegal, so he wooed her over, which I’m guessing involved comparing notes on favorite Brittany Spears lyrics and complaining about how boring high school chemistry is. Maybe while listening to Third Eye Blind songs. I don’t know.

No surprise, their marriage didn’t work out.

After dinner we went back to my little Tampa beach shack and started watching TV. We made the awkward small talk that is often saturated with extreme sexual tension, and when I kissed her, things got intense quickly. My hands explored every inch of her body, caressing her incredibly perky C-cup tits, cradling her neck in my hands, kissing her softly and running my fingers through her hair. For a woman that had two kids, her body was incredible.

“Your body is incredible,” I told her.

I took off her shirt, then my shirt, then her bra, and we continued kissing for a couple more minutes. Then when we came up for air, I motioned towards my bedroom.

“You wanna go in there?” I asked.

She hesitated. “Yes. I want to. I just…”

Oh God.

Hesitation, for me, means it’s not happening. Pressuring women into sex or lobbying for it always makes me feel used car-salesman sleazy, and I want my partner to reach that conclusion on her own. This is especially true with single mothers. So while I want to tell you that I talked her into it, in the continuum between Protestant guilt and Neanderthal sex addict, in that moment the Protestant guilt side of me blew off the cobwebs and took over. My night with Leslie was also extremely early on in my Internet dating foray, before my moral compass was tossed overboard, so Leslie and I put our shirts back on and uncomfortably watched TV for another hour or so before she had to leave to pay the babysitter.

Feeling guilty for fucking a single mom is, of course, ridiculous, because single mothers want to get fucked as much as anyone (possibly more), and just because they have a kid does not mean I should discriminate against giving them what they want. Maybe I’m concerned I’ll actually like them, and that I might fall for them, and if that happens I’ll have to navigate a step-dad/biological dad/tiny humanoid situation, and all that is too much to deal with. Or maybe I can’t indiscriminately fuck someone I don’t really care about because I know they’re responsible for an innocent child, and it feels like watching a porn star get fucked after being introduced to her parents. Who knows, but instead of saying to her, “Come on, you know you want to,” or some other rapey thing, I said, “Okay. You’re right. It’s probably best we take it slow,” and lifted her up off my lap.

All single mothers should not be ruled out just because I’m a weirdo that gets in my head about it. Take it from my friend Will. He got involved with a woman named Nova who was mother to a six-year-old boy, and other than having a cool and unique name, she defied the tragedy of single motherhood. First, despite the fact that a little human once exited her vagina, her pussy was apparently miraculously nice. Second, things got physical quickly because whenever she had a free moment she was down to screw. No hesitation with Nova. Third, she was enthusiastic in the sack and interested in getting laid as much as possible. Most importantly, she wasn’t above sucking dick, which seems to be a rarity for women over 30. There’s nothing better than an enthusiastic fellatio artist. With Nova, biological dad was still in the picture, but she was smart enough to know that Will getting too involved would complicate things. But after a few months of boning, it became clear that Nova wanted something long term and Will didn’t, so things were not working out, but in the short term everyone got laid, Will and Nova had a great time together, and her little gremlin kid didn’t have to get all confused about who his father was.

Single Mothers are tricky, because a kid adds a lot of complexity to the situation, and like pretty much every other dating situation, adding complexity is invariably not a good thing. Every Single Mother will be different, and depending on what kind of person you are, your approach to them will be different. Unfortunately, there’s really only one category of dater that Single Mothers are especially attractive to, and that’s Single Fathers.

A Note on Having Children

One thing Leslie and Nova both had in common was that they did not bitch about the fact that they had kids. They also did not constantly preach about how difficult parenting was. Anyone that does either of those things should have their urethra cauterized. When you have a child, you give up your freedom to do exactly what you want, so if this is a surprise to new parents they get no sympathy from me. There’s a key point here that a lot of people do not seem to realize: Having children is a fucking choice! So if you’re complaining about how tired you are, or how you haven’t seen a movie in a long time, or that you have no social life, you probably should have thought about that before having kids. If you and your partner fuck and nine months later a baby came out, this should not be treated with the same level of shock as, say, winning the lottery or an asteroid destroying Washington, because that is literally what is supposed to happen. Having kids is not a surprise, because the little monster gremlin fuckers are everywhere – at the grocery store, at the park, schools, playgrounds, at shopping malls – you can see the deadened look in their parent’s faces. I’ll be at a coffee shop and some couple will walk in with their kid. The little demon will be crying and drooling, with 30 percent of the morning’s apple sauce meal spilled on its T-shirt, and the parents just stand there with vacant, haunted stares, thinking about how the rest of their day is going to be devoted to corralling this little shitting, vomiting, screaming parasite with the sleep patterns and patience of a meth addict.

Finally, a lot of people say ‘congratulations’ when someone is pregnant or about to have a baby. I do this too, but why? Why do we say this? That person who is pregnant did something that was extremely enjoyable (or a crushing disappointment, delete as applicable) and then just let biology do the rest. Voila! A baby popped out nine months later. They literally could have laid flat on their backs while the father of that frankespawn blew a load up them, then continued on with their unmemorable life, probably continuing to be the fat slob they were before the pregnancy, and now we’re congratulating them for that? Seems totally nonsensical if you ask me. Congratulations are the last thing we should be offering. We should be tendering our most sincere condolences while wearing a black armband and weeping genuine tears of sorrow.

Professions and Other Life Circumstances

Generally, the first thing people ask when they meet someone is what that person does for a living. That’s because knowing what people do for a job is a convenient shorthand for what it might be like to interact with them. For example:

Teacher = sweet and patient, but will complain they work too hard for too little money, because every teacher does this.

Construction worker = gun owner. Votes Republican. Probably homophobic.

Marriage and family therapist = disturbing family past led them to this profession, and they probably have more horrendous issues than the patients they see.

You get the idea. This can be a very effective tool in dating, because there are certain categories of people out there that appear over and over, and while implicit bias for people’s professions is totally unavoidable, it often saves time. Here are some common professions for females that I found on the swipe-apps, with special focus on large cities like New York and L.A.

College Graduate (Usually in Advertising, Sales, or Marketing at Some Tech Startup)

First off, I get that ‘College Graduate’ isn’t a profession, but if someone has just recently graduated, you can be pretty certain that they’re in advertising, sales, marketing, or they work at some tech firm like Google, Groupon, Facebook, or Yelp. They are pretty much all the same, and I’m not saying that person isn’t a unique and beautiful snowflake, because they may rise to be the CEO, but they have to start somewhere, and they usually start here – at the bottom. Anyone in this category was probably a communications major, likely female, and they have a pretty good chance of being attractive. The female College Graduate is the holy grail of swipe-app dating, and the prime age to catch the college graduate is about one to two years after they graduated, age range 24 to 26. At that age they are sufficiently removed from their close circle of college friends, and they feel the desperation of meeting new people in the real world. The comfortable social safety net of college is no longer something they can reach for, and especially if they’ve moved out of the area from where they went to school they quickly realize that meeting cool, intelligent, and attractive people to hang out with is incredibly difficult; especially one of the opposite sex.

The further you get away from college, the smaller and dirtier the dating pool gets. The College Graduate is feeling the hands of time turn inexorably on, so they’re a little bit desperate, but more importantly they are also still very hot. As I write this, I’m 32, and when you’re between 24 and 26, people who are in their thirties seem ancient. I’m sure I’ll still long for a College Graduate when I’m 50, because I think every man does – the difference is I’ll be an old pervert then rather than a younger one, so I’ll probably keep that opinion to myself. But if you’re a male College Graduate looking for a date and you fall in that age range, you need to immediately get on the swipe-apps right now, because it will never be this good for you ever again. Unless you plan on being worth $100 million, there is a short window of time in which you can fuck girls in their twenties.

Verdict: Go for it.


Obviously most prevalent in N.Y.C. and L.A., there are more actresses on the swipe-apps than any other profession. I spent the last year or so living just outside Los Angeles, and I swear every third person on Tinder was an actress.

There are two types when hunting these abundant creatures:

1) The ‘I’ve been told I’m pretty since the first moment I grew boobs’ actress.

2) The ‘I’m a quirky free spirit that’s into theater so I’m going to be an actress’ actress.

Whichever one you come across you’re going to be dealing with a troubled, difficult human. The former will think her shit don’t stink and the latter will be blasting The Beatles at midnight while you’re trying to sleep so you can wake up early and go to work to support her struggling career. She will argue that she needed those three years living in Thailand in order to find her ‘passion’ and ‘true calling’ while you were getting a graduate degree, but really she was just fucking tourists who visited the island and staying tanned 365 days a year. She found her ‘true calling’ all right, and that was to call herself an actress and ruin your life. Also, she’s probably bulimic and you really don’t want that shit.

Venturing out on the swipe-apps is really an act of desperation for anyone, but especially actresses, because most actresses on the swipe-apps are approaching 30, and an actress approaching 30 does not need to be reminded that she has no work history or marketable skills to fall back on. Internet dating is a sign of giving up for most people in their dating lives, but that’s especially true for actresses. It’s a silent admission that they might not ‘make it.’ They are starting to realize that their only chance of the life of glitz and glamour they’ve always dreamed about is to find an old, attractive-enough sugar daddy with high, possibly lethal cholesterol levels. The residuals from the one tampon commercial they did five years ago isn’t moving the ball forward, and they’ve turned to the swipe-apps for those few remaining recently divorced business tycoons or nerdy corporate lawyers who are just starting to realize they can get chicks because they have money.

If all you care about is how fuckable your current partner is, then the Actress might be in your wheelhouse. Just as there’s a lot of dudes overachieving with Single Mothers (or divorcées), there are plenty of Hugh Hefner wannabes willing to accept the fact that the only reason their sex partner is with them is because they want to ride around on a private jet and take trips to the Caribbean every six months. Many of these women are not even trying to be actresses; they are just trying to be exactly what they’re portraying on Instagram: Girls who like really nice, expensive things who are willing to exchange sex for never having to fly on a commercial airline their entire life (it’s private jets only for these succubi).

The upside to actresses is that they are almost certainly going to be at least better than average looking, but there’s a lot to be wary of. First, their photos are probably professionally done headshots that their parents paid for when they were 23 that are finally being put to good use as a swipe-app profile picture. Second, actresses are extremely well-versed in putting on makeup and making themselves look good, so even though their headshots won’t land them a leading role in the next David O. Russell film, it will vault them to the cream of the crop among attractive Tinderers, and they probably can choose from whomever they want.

Most actresses will not actually be willing to go on a date with anyone they meet on the Internet because they are searching for that rich, older business tycoon, or because they have outsized, unfounded confidence in themselves and are too picky. More than likely they just need validation after facing rejection all day every day in an industry that’s brutally competitive and full of gorgeous people. Nothing wrong with ambition that borders on delusion, because someone has to be on TV, but false confidence is nauseating in a person you’re trying to date. If you’re after an actress, she will almost certainly think she’s better than you, and she might be right, because she’s probably going to match with every single guy she swipes right on. Finally, the whole swipe-app thing might just be a fun game for her that she plays with her friends when she’s drunk. Chasing after actresses is a fool’s errand, and the upside – that you’ll find one who will probably just end up ruining your life – is minimal.

Verdict: Unless they’re actually talented, they’re your high school sweetheart, or they’re already famous, steer clear.

Hair Stylist/Makeup Artist

My sense of style is best described as ‘Accountant Dad,’ and these chicks tend to want someone ‘fashionable’ and ‘edgy,’ so despite wanting to date a hair stylist/makeup artist, I’ve not successfully been able to do so. This might seem like a totally bullshit profession (and it may be in many cases), but the Hair Stylist/Makeup Artist can also be a great catch because while seemingly bullshit, it can actually be pretty lucrative. Women everywhere obsess over hair and makeup, and if the Hair Stylist/Makeup Artist combines a little ambition with some hustle, they can rake in the dough. Not to mention they will probably work great hours, they will be very passionate about their job, and hopefully love what they do. If they’re really hot, they are one blog post or YouTube video away from printing money as an Internet celebrity.

They will most likely have great hair and/or makeup, and more generally, women that care about this stuff generally care about their personal appearance, which is nice. I plan on working hard to look as good as I can for my partner, so it’d be nice if someone put in the effort to have their good looks stretch far beyond their college years. Fake tits. Workout warriors. Lululemon yoga pants. Everything you could ever ask for in a trophy sex partner, these women are into it. And just because they’re a trophy sex partner does not also mean they can have great depth. Lie to yourself all you want, but attractiveness matters.

I also like the idea of dating one of these ladies specifically because I won’t have to think about fashion. Most men do not want to think about what stupid pair of pants goes with what shirt, so it’s nice to have someone make those choices for them. If that person is also their smoking-hot model girlfriend who they get to fuck later, even better.

Careful, because many can be a wolf in sheep’s clothing, and if they’re heavily tattooed with multiple body piercings, it might also indicate they’re a little bit nuts (I personally think some heavy tattoo art is kind of sexy, and I suppose that’s more of a ‘wolf in wolf’s clothing’ situation, but I digress). The other danger is that their profile might say they are a ‘makeup artist,’ but really they’re just sitting in their room listening to Death Metal while applying excessive amounts of dark eye shadow before self-harming.

Verdict: These are a mixed bag.

Anyone that Graduated from the Fashion Institute of Design & Merchandising

This person is a trust-fund baby who graduated from a made-up school that teaches you things you could just learn on your own. This person doesn’t want to work and is waiting to marry rich. Probably very attractive, because FIDM is super expensive, but will also ruin your life and take half of everything in divorce.

Verdict: You’ve been warned (unless you’re a gold-digger who doesn’t care about your own sanity).

Yogi/Yoga Instructor

As prevalent as actresses on the swipe-apps, the Yoga Instructor is the female version of the male personal trainer. These ladies are fit, usually very attractive, and always seem to be in a good mood. One out of every two women on the swipe-apps are ‘into’ yoga, but these ladies are taking their ‘practice’ to the next level by paying $4000 to take a Teacher Training class, wearing bangly jewelry and yoga pants everywhere, misinterpreting Sanskrit texts, and getting Henna tattoos. The Yogi ranks second only to the College Graduate on the swipe-app Power Rankings, but is still somewhat hit-and-miss. Knowing your enemy can be the difference between mounting a smoking-hot blonde positioned welcomingly in a downward dog or jerking off to instructional yoga videos, so pay attention.

First off, you might think, “If I wanted to meet a Yogi, why wouldn’t I just join a yoga class instead of getting on the swipe-apps?” Rookie mistake. You see, despite the fact that the female to male ratio in your average yoga class rivals the sociology department at a Christian University and features very toned bodies decked out in extremely tight fitting spandex, yoga class is actually a horrible way to meet a young, hot, free-spirited yogi. If you’re going to try to date a Yoga Instructor by actually attending yoga class, at the very least you’re going to have to play the long game, because the women who go to yoga class are not there to find a date. This is their workout, and they want to be left alone. For men with enough courage to approach a woman and talk to her, no location is out of bounds, but the yoga class should be, because it doesn’t matter if a man thinks a woman post-yoga workout is hot and sexy, if she doesn’t feel sexy she doesn’t want to be hit on.

You also walk a fine line when you’re a man that enrolls in yoga, because you immediately register as a giant enemy threat on the collective radar of that estrogen-soaked epicenter of Namaste that is your local yoga class. Either you’re there because you’re really into yoga or you’re there for the tight fitting yoga pants, and the collectively off-the-charts estrogen levels can smell your motivation immediately, so if you think you’re going to get some action by just showing up and learning a few poses, think again.

Verdict: Unless you’re really into yoga, then from Uttanasana to Savasana, good luck.

Free Spirit/Profile Picture of Burning Man/Some Made-up or Goofy Profession

Usually masquerading as a yoga instructor but in fact will be borderline homeless, these women will try to be coy or playful about the fact that they are currently doing absolutely nothing with their lives.

Profession titles include:




Free Spirit


Professional Bad Ass

Educational references include:

School of Hard Knocks

Hogwarts School of Witchcraft and Wizardry


Likes include:

Burning Man



Live Music

Father John Misty

James Vincent McMorrow


Unless you are also one of these people and you’ve found your soul’s reflection in another, you need to stay far, far away from this type. People who are wandering should keep wandering and figure their own lives out before adding someone else to the mix. If they are truly comfortable being unemployed or a professional traveler or whatever, they would not be on the swipe-apps. They should probably be able to find a date at the next music festival they attend, and if they can’t, they aren’t doing enough Molly. They need to get their priorities straight.

Verdict: No.


Seems great, right? How can you go wrong with such a distinguished, lucrative, highly regarded profession?

Let me tell you.

I’ve met two doctors from the swipe-apps, and both were completely insane. I don’t know if doctors are nuts because of the stress you have to go through to become a doctor, or if you have to be crazy to want to be a doctor in the first place, but I haven’t met a single, sane female doctor yet. As my friend Will pointed out to me once, you are not an attractive female doctor and still single in your mid-twenties unless you have some serious, serious issues. There will be a lot more discussion on the topic of doctors later in this book, but let me give you a little preview:

Annie, a third year resident at UCLA David Geffen School of Medicine, could not sleep without wearing noise cancelling headphones, I could see from the pictures in her apartment that she’d gained 30 pounds since college, and was so awkward that you could cut the tension in the room with a knife. She was the kind of person that you had to grab by the shoulders and shush to a calm in order to have a reasoned conversation with. She was so high strung and stressed out, just sitting and watching TV with her felt like a chore. I actually commend her for this, because it all derived from how seriously she cared about succeeding in her profession, and that seems to be exactly what I would want in my doctor.

But lying awake in the dead stillness of her room after fucking her missionary style for 15 minutes was too weird, and when I looked over at her lying like a mummy with her noise cancelling headphones on, I knew I had to get out of there. So I did. And never went back. Yet Annie was the picture of health compared to Alyssa.

Alyssa was a substance abusing, dysfunctional, and emotionally unstable train wreck. She was also sexual napalm. She wanted sex and she wanted it all the time and in all sorts of ways – my dick in her asshole, fingers in assholes, my dick in her mouth – she was insatiable. Alyssa was only 33, but she’d done so much Adderall to get by in medical school and residency that she looked like a 40-year-old crackhead that was a mere six weeks into recovery. We fought, argued, and fucked our way through a three-month relationship until I couldn’t take it anymore. The first whiff of an argument between us and Alyssa would start bawling her eyes out, making threats, and saying the nastiest things she could think of. Then she’d wake up the next day and go treat patients at the hospital.

Verdict: How are these people practicing medicine?


I went to law school. Lucy is a lawyer. Verdict: No.


Of course this is not an exhaustive list, and an elementary school teacher or a high school counselor or engineer or computer programmer I’m sure would be a pretty great catch. But for whatever reason, there’s a lot less of them than there are actors, models, makeup artists, lawyers and doctors. This chapter was all about who you might meet online, based on the people I met over the last couple of years, and the next couple of chapters are about what happens when you actually meet them.

When I turned to the swipe-apps, I fueled a self-destructive yearning to get over my break-up with Lucy with the one thing that’s broken up kingdoms, displaced dynasties, driven men crazy, and that permeates our contemporary lives. It’s the one thing that everyone wants, but not everyone figures out how to get: Sex.

And I got it.

Chapter Four

Part One: Sex

“Was it good for you?”

My sexual stamina is as consistent as a Florida rain. I could prematurely ejaculate after three shallow pumps, or put on a Casanova-like display of love-making that would make a jaded Jenna Jameson squeal. What causes the difference in these two performances and the spectrum between them is anyone’s guess, because I’ve found no correlated factors. Hopefully that’s obvious, because if I knew what caused me to be a shitty partner in bed, I wouldn’t be a shitty partner. Problem solved. But it’s not so easy, and premature ejaculation is especially damning in a relationship because you don’t get a second chance to make a first impression, and if your first impression is that she would have been better off with a bottle of wine and a Nicholas Sparks novel, you’re fucked. Or rather you’re not fucked. Not ever again (with her at least).

Also, there’s no guaranteed way to fix it, as my research has shown that the common urban legends are either wrong, or they don’t apply to me.

For instance:

1) If you’re drunk, you’ll last longer.

Not true. I’ve been hammered drunk and blown my load in two minutes, and I’ve been dead sober and lasted for a half-hour.

Another one:

2) If you’ve recently ejaculated, you’ll last longer.

Also not true. I could be abstinent for six months and be a total stud in the sack, or I might have had sex the same night and still blow my load so quickly it might as well have been my first time. If she’s lucky it might add two or three minutes to her clock, but really – who’s counting? I know I wasn’t.

My first time with Lucy, with my ass bleeding all over the sheets of her tiny twin bed on the night before she flew to New York, I wasn’t a horrible lay but I was far from great – closer to premature ejaculation than Casanova. In other words, my usual ‘below average’ self. But she finished happy, and just like she would throughout our relationship, she made me feel comfortable before, during, and after. She didn’t berate or embarrass me for my tiny dick, ask me to leave or pressure me into taking recreational Viagra because I came too soon; she just shrugged it off. With Lucy, sex wasn’t performance art.

She also orgasmed faster than anyone I’d ever met. Maybe she faked it that first night (maybe she faked them all…), but her generosity and quickness to climax still made me feel awesome. The quality of sex is often directly proportional to how much my partner enjoys it, and sex with Lucy was great because there were obvious signs when things were going well. She would moan loudly when I entered her, her face would turn red when she was really turned on, her tits would get really firm, she’d arch her back when she rode me, getting louder and louder as she got closer and closer to coming, and after we got really comfortable, when she did orgasm, she’d announce it. The deranged narcissist in me loved hearing her scream out when she was coming, and I wanted to hear her exhale a sigh of orgasmic relief after we fucked. Men need obvious cues, and the combination of cues from Lucy made her much more fun to screw than someone who acts like they’re boning out of sheer duty.

She also looked incredible naked. Her natural, gorgeous, full C-cup breasts were a gift from God, and nothing would turn me on more than when Lucy and I were having sex and she’d be on top, riding my dick, and I would reach up and massage her tits. She would throw her head back in ecstasy and moan loudly, bracing her hands on my legs or chest; I would get harder and harder as she rode back and forth, up and down, until she reached orgasm. She had a gentle face, with full lips that would curl into a curious smirk when she was getting ready to call bullshit on something dumb I had said. She had long, slender legs that seemed to go on forever. Her blonde, silky hair gave her the pristine image of a goddess, and just a glance in her direction would turn me on.

She was also the perfect size – five foot seven and a 125 pounds – so I could pick her up fairly easily. I would be fucking her missionary and she’d wrap her long, slender, forever legs around me, put her arms around my neck, and I’d scoop her up with my hands at the small of her back. I’d raise her up off the bed so we were both vertical and she was in my lap, supported by my rock-hard cock inside her and my hands embracing her. I would cradle her like that, thrusting in and out, rubbing her clit with the shaft of my cock, driving her wild.

The sex was incredible, but it was never just fucking with Lucy because I wanted to be everything for her. I wanted to be whatever she wanted – gentle, violent, passionate, aggressive, compassionate, patient – and once we got comfortable and knew the rhythms of each other’s bodies, I’d like to think I was. There’s no love like your first love, there’s no sex like sex with the first person you’re in love with.

Getting Comfortable

After failing to truthfully divulge my desire to abandon my law school studies, I returned to L.A. for the next semester of law school. Lucy and I started seeing a lot more of each other, falling into the familiar rhythm of two Type-A high achievers trying to get by. We went to class, worked out together, went to library together, and made love late into the evening. Because of my inexperience, during those intervals of love-making, I had no idea if I was doing anything right. Little did I know, Lucy was my perfect dance partner because she wasn’t all that experienced herself, so we learned to dance together, and she was there to see me go from a nervous, bumbling mess into fucking her like the world was ending. I’ll never forget the night that it clicked.

It was a spring night in April, and we were falling asleep next to one another in her Culver City apartment. It’d been a couple of days since we last were intimate, mainly because I was still perpetually afraid of being a disappointment in bed, and also because I always wanted to be at my best when we screwed. If I had the slightest stomachache or whiff of uncertainty about my performance, I would shut down. Just being with her was enough, and I didn’t want a bad performance in bed to be the reason I lost her. We were lying there under the sheets when she turned to face me and asked,

“Do you not want to have sex with me?”

I was genuinely shocked. “What? Of course I want to have sex with you.”

“Well, it’s been a couple of days…” she said.

That was the only cue I needed, and I rolled over and kissed her deeply. I touched her body everywhere as blood filled my cock. Soon I was frozen-pipe hard and we caressed each other in the heat of feverish passion. I got on top of her and kissed her over and over, cradling her head in my hands. I rubbed her clit gently over her underwear and she moaned, wrapped her fingers around me, and guided me towards her. She practically ripped off my shirt. I lifted her up and tugged her T-shirt over her head. We locked eyes and knew. Pants came off. I slide inside her missionary style and nibbled at her ear. She dug her nails into my back as I slowly thrust in and out. I grabbed her neck with both hands and brought my lips to hers while still inside her; her breath hot with lust; her tongue swollen and moist as I entered her over and over. I turned her on her side and fucked her sideways. I pulled her to the edge of the bed and fucked her missionary style with her legs together while she squealed with delight. I wrapped her around me, picked her up, stood, and suspended her in the air while I pile-drived her over and over until she screamed out in ecstasy. I spun around, sat on the edge of the bed, still inside her with her in my lap, my hands under her butt, and with my cock wedged deep I circled her hips around the base of my shaft. I wrapped my arms around her back, pulled her close, and brought her wet mouth to mine. She lightly said my name in a passionate exhale, and when I started thrusting again, she gasped louder and louder for breath until she announced that she was coming, her face an expression of so much pleasure it appeared almost painful. I set her gently back on the bed, turned her on her stomach, and slide deep inside her from behind. She moaned loudly. I slowly slid in and out of her, massaging her clit until I couldn’t take it anymore. I remember thinking there was no way sex could get better than that chilly Spring night. In questioning my virility, something carnal and wild opened up inside me, and I fucked her like a crazed animal. I screwed her with the intensity of a newly released prison inmate, and the passion of a soldier returning from war. That was the night a switched flipped inside me, and I realized what I could be and what we could be together. No one wants to have to ask for sex, especially a woman, and that was the last time she ever had to.

Pornography and Unwanted Teenage Celibacy

Once, towards the end of our relationship, Lucy and I tried to calculate how much sex we’d had: Once a day, and sometimes twice a day, for two years. At least a thousand. Early on, I felt like I could have had sex with her forever. But for every gorgeous woman out there, there’s some dude who’s tired of fucking her, and after the thousandth time I started to get curious, and I got curious because I was bored. To satisfy my curiosity, I turned back to the one place I learned about sex: The Internet.

Hitting puberty during the rise of the digital age, when Internet speeds started getting very fast, I was just another pimply-faced teenager who was a few keyboard strokes away from the most diverse and graphic library of sexual imagery man had ever seen. Being a sexually repressed teen full of hormonal rage, jerking off was like manna from heaven, and porn was the lever that made it rain manna in 0.3 fluid ounce loads. Ten-inch dicks pounding away at meticulously shaved vaginas, prosthetic over-sized double-D tits, perfectly styled hair flowing down in front of unblemished female faces, group sex where everyone is screwing like it’s the end of the world, sex with midgets, sex with Asians, tiny women getting double teamed, gangbangs, threesomes – it was like a menagerie of sin playing out before my (quite literally) virgin eyes. Porn was a world where people fulfilled their every hedonistic urge, and where the animalistic grunts of stylized actresses made it seem like they enjoyed sex just as much as men. It was, of course, a perverse and unrealistic reflection of how sex really is, but nevertheless I wanted to make women lose their minds in the same way the female porn stars did when some muscle-bound Neanderthal violated her.

Men who watch porn watch it with the mistaken belief that they might one day be able to have sex with a woman that wears heels to bed, bleaches her asshole, has the libido of a rabbit, and always looks like she’s fresh from a spa treatment. Like the homeless man’s version of the movie star, they are designed to incite lust, with basic features of beauty like a low body fat percentage or a pretty face, but with bleached hair, fake eyelashes, tanned and toned bodies, endless surgical enhancements, and exaltations of pleasure that are so theatrical they often seem almost comical. The things I saw on the Internet, whether as a teenager or the videos I came across to jerk off as a relief from boring sex with Lucy, expanded the possibilities and stoked my curiosity.

Sadly, as a teenager I was the guy that never got laid, so my burgeoning sexual curiosity, combined with my paralyzing fear of pretty girls, made me one sexually repressed weirdo. By the most liberal of estimates, at 20 years old I’d only been intimate with a half-dozen people. A couple thousand times sleeping with Lucy was awesome, but it became mundane. I wanted to do other stuff than just switch positions a bunch of times, orgasm together, cuddle, and fall asleep. I can’t say that blowing my load on her face was something I was dying to do, because blowing my load in any woman’s face seemed way too degrading. Even when a porn star gets blasted with man juice, not even she can hide how disgusting it is. But even if I wasn’t currently interested in delivering a money shot to the angelic face of some serene beauty, or sex with a midget, I wondered what it was like to do anal or to ram my dick down someone’s throat. A threesome sounded fun and adventurous. What about sex with a couple of Asians? Growing up, it seemed like most of my friends had already done that stuff, and I had to see what I had missed. If I didn’t satisfy my curiosity, cheating seemed inevitable. But I still cared for Lucy, and you don’t throat-fuck someone you truly care about – right?

My curiosity wasn’t just about the sex acts; it was about experiences. There are roughly 3.52 billion women in the world, and here I was having my first real sexual relationship with one of them. How was I supposed to be satisfied limiting myself to that experience? Shouldn’t life encompass more experience than just one out of 3.52 billion? I knew I had a gorgeous, classy, refined, intelligent woman who was willing and eager to have a lot of sex with me, but I wanted more. I wanted more sex, of more variety, and with someone new – someone hotter, with larger tits, a plumper ass, a runaway libido, and with someone who wore heels to bed and bleached her asshole. Am I as pathetic as I feel for wanting this? Or am I just a man?

The Perils of Indifference

Something else happened. Law school was coming to a close, the shine of our relationship had worn off, and I started to notice little hints of her checking out. We’d pass each other in the law school hallway and I’d register a look of mild annoyance on her face, she’d roll her eyes at something sweet I would say, she’d kiss me in a cursory, distracted fashion when I was trying to start something sensual, or she’d offer what looked like feigned enthusiasm when I asked to hang out.

My curiosity might have been a minor fracture, but my perception of Lucy’s indifference was more like a rift. If women can smell fear, men can smell indifference, and dragging things out when you are slowly losing interest in your partner is the worst, meanest thing you can do, because it steals the one thing you can’t get back: Time. This is true especially if you’re a woman, because there is nothing more damaging to a man’s ego than a woman who begrudgingly continues a relationship with him. When she balked at hanging out, or rolled her eyes in mild annoyance at something I said, or when she’d get embarrassed by me, I felt like she was dragging me over hot coals. If she felt that way, why didn’t she just end it?

I started to panic. My curiosity and her indifference brewed a sense of desperation in me, and I figured that if this was going to be the end of things maybe I could at least get some new sexual experiences out of it. Or better yet, maybe wild, exciting new sex acts would revive whatever was dying inside us both and things would work out.

Finally, I brought it up.

“Have you ever done anal?” No.

“Do you want to do anal? No. (Classy girl.)

“Are you happy with our sex life?” Yes. (Said with the conviction of a middle schooler reading aloud from Hemingway.)

“Is there anything you want to try?” No.

Well, goddamnit. That didn’t work.

Lucy might have been my perfect sexual partner because she came fast and had a perfect vagina, but her bluntness stalemated me and I panicked more. I never brought it up again. Instead, I started to pick apart Lucy’s flaws so I could hold them against her. (Classy guy.)

For instance, despite having gorgeous, long, slender, toned legs, Lucy’s ass looked like the ass of an 80-year-old toll-booth operator that wore baggy corduroy pants to work every day for the last 50 years. She was a late-twenties law student who was committed way more to academic research than she was to staying fit, and I couldn’t help but think things were only going to get worse. The signs of her turning into a frumpy old lady were already starting to show, and images of her walking around the house wearing baggy, unflattering sweatpants and fraying-at-the-collar triple XL sweatshirts haunted me. Unless she planned a drastic career change to Olympic sprinter or personal trainer, it didn’t take clairvoyance on my part to see my attraction to her was going to fade. It was already starting to.

I tried to focus on how lucky I was to have her in the first place, but after every roll of her eyes or indifferent brush past me that stung my heart, I’d refocus on those flaws and make a critical slight in my head. Like the fact that she had horrible posture. Years of hunching over a desk, lugging a heavy backpack around, and pouring over academic work had rounded her shoulders, creating a little paunch on her stomach, like a kangaroo carrying a joey. It wasn’t that she was fat, but she was just fat enough, and she carried it all in that little front pocket of her waistline. When I said something about how we should both start sitting up straighter, given all the reading and deskwork that we did, she took it as pure criticism and it only made things worse.

All the flaws I once so easily ignored, and even embraced, I started to use as ammunition for some unconfirmed and possibly completely fabricated problem. I didn’t think enough about how I was lucky to have Lucy in the first place, and I didn’t appreciate her normalcy. I also didn’t appreciate that the porn-star hot women that my wandering eye might be drawn to were all batshit crazy, with more daddy issues than a child abuse victim. I didn’t know that all the sane, pretty women in their mid-to-late twenties were either married, had boyfriends, or had the luxury of breaking up with a different guy every hour or two, so would never stoop so low as to date me. I didn’t know how miserable the hedonic treadmill of love was, and that just because DiCaprio, Clooney, and the dried old prune Hugh Hefner got to fuck beautiful women in their twenties for their entire adult lives, didn’t mean I would get to do the same. Instead, I slowly continued to sabotage everything good about our relationship, and all it took was a final few pushes that sent a future with Lucy tumbling over the cliff. The biggest push came from the life decisions we made.

A Time Apart

Law school was drawing to a close, and I thought that if Lucy saw me as a more serious person, instead of someone who planned on graduating and traveling around like a fuckwitted vagrant, it would change things. In a quest for legitimacy in her eyes I frantically applied for jobs. Unfortunately, ‘listless, mediocre law student who lacks motivation to practice law’ does not look great on the résumé. Then, one spring day in February of 2012 I drove to the Navy recruiting district office building in El Segundo for an interview with the Navy ‘JAG’ Corps. The Judge Advocate General Corps is the legal department for the United States military. Each branch – Army, Navy, Marines, Coast Guard – has their own ‘JAG Corps,’ and I chose Navy because the movie A Few Good Men starring Tom Cruise, Jack Nicholson, and Kevin Bacon had made the Navy lawyers seem the coolest. In reality it was just another job interview, because I would take whatever I could get, and I figured my long, floppy hair and casual personality would clash with the close-cropped, uptight military lawyers that the JAG Corps generally selects. But of course, by virtue of not caring, I performed exceptionally well. Just like a first date. Ten weeks later in early May, just weeks from graduation, I got notification that I was selected. I thought this might be the achievement glue to keep Lucy and I together, so I excitedly told her the news.

“Oh. That’s great. Congratulations,” she said, with as much enthusiasm as though I just told her my colonoscopy results. Whatever. Spiking pebbles in the sand during a lonely evening beach stroll started to seem grim, so even if I didn’t really care too much that I had a job, perhaps it was for the best.

In June I went through the paces of law school graduation, somehow limping through the three years and securing a job before walking across the graduation stage. That summer Lucy had an internship at the U.S. Attorney’s office in San Diego and I studied for the bar in L.A., where I was finishing out my lease with Jordan, Drew, and another law school friend I roomed with. I visited Lucy on weekends, and maybe the distance did us some good, because the summer breezed by. In the fall she moved to Washington, D.C. for an internship at the Department of Justice. I’d passed my medical screening with the Navy and my officer training didn’t start until November, so after I took the bar I moved into her little sublet apartment off B Street, right by the Capitol Mall. For the time being, although we were somewhat apart, things were working out. Then in November I left D.C. for Newport, Rhode Island, where I’d complete five weeks of ‘Introduction to the Military’ training. Lucy and I started talking less and less. With law school graduation now looming for her, she was having the same difficulty procuring post-grad employment that I did, so when we did talk, she was stressed. It was hard to watch her struggle to get a job, because unlike me, she was actually bright, with limitless potential – a high achiever, with great grades, who’d been published multiple times. I tried to be sympathetic, but my sincere encouragement came across as annoying criticism when I told her she needed to be more assertive in interviews and that someone must hire her given her impressive résumé.

When my training ended we spent the winter holiday apart, her with her family on Long Island and me entombed in the mortuary that is my parent’s home. I stopped to visit her in L.A. after the New Year, hoping my visit would rekindle what I felt we were slowly losing. I had to be back in Newport for more training in a week. During one of those crisp January days during my visit, we were standing in the sunshine of the USC Law School Commons amidst the cafeteria workers, lap-top carrying students and odd-ball professors, when she asked me to sit down. She said it in an oddly formal way that made me think, Oh no. This isn’t good.

“I got a clerkship!” she said. (The home run of legal job offers, this was her goal all along.)

“That’s awesome! Congratulations! Where?”

“In Guam…” She trailed off.

“What’s that?” As though she were referring to an exotic vegetable.

“An island.”


“In the Pacific Ocean. It’s by Hawaii,” she said. I pulled out my phone and google mapped it. Saying Guam is ‘by Hawaii’ stretches credulity, because Guam is ‘by’ absolutely nothing. It’s a tiny, remote island in the western Pacific Ocean, just 210 square miles in size.

“The Navy is there…” she offered.

“Yeah, but it’s not like I can get them to just send me there. I wouldn’t be able to get to Guam for at least another two years. At least. How long is the clerkship?”

“One year.”

I looked at my feet.

“I’m really excited.” You could hear in her voice that she was. “I think I’m going to take it.”

I stared at her blankly. Finally, she asked, “What do you think?”

I wish I had said, “The only reason why an American civilian would end up in Guam is if their cruise ship capsized on the way to Hawaii. There is literally no farther place on the globe that you could be moving to. How can I not take this as an insult?”

That’s what I should have said. Instead, what I said was,

“We’ll work it out. It’s really far away, but we can make it work.”

“Really?” she asked.

No, not really. Why the fuck are you asking me that? It’s not even Canada! Or Mexico! Or South America! Shit! It’s not Hawaii! Hawaii would have been better news!

“Yes. It’s all right,” I said. “I can tell you’re really excited about it, and you should do it. We’ll just have to make it work.”

The Navy was sending me to Florida, so maybe I had no right to be angry, but I didn’t intentionally move 8227 miles away, and she did. This is the game I played in my head, but she had such a hard time getting a job, and she seemed genuinely excited, and in my mind I pictured us scheduling regular vacations to see each other in Australia, or Morocco, or Belgium, or whatever fucking country was halfway between Guam and Florida. I suppose I didn’t realize how angry I was at the time, but I’d soon realize just how much of a kick in the nuts this was.

The First Transgression

Part of being a lawyer for the U.S. Navy means they send you wherever they need you to go, and the Navy needed me in Florida, so in March of 2013 I went. I started my job, communicated with Lucy when I could, and time and distance seemed to slowly suffocate the flames of what we once had.

In May I flew to Austin, Texas, for a college friend’s bachelor party. There, I found Jenna. She had a body like a sports car, gorgeous long brown hair, and a beaming smile with bright, vibrant eyes. She was a basic bitch, which is just a pejorative term jealous people use to describe spectacularly ordinary beauty whose beauty isn’t ordinary, it’s rare, and even they don’t have a totally unique style every man still wants to fuck them. She had a runner’s body, C-cup tits, and a flirtatious demeanor that screamed sensuality.

The drunken frat-boy crew of bachelor party attendees was stumbling home smashed one night, and suddenly I got a text. I didn’t remember exchanging numbers with her, but there she was: Jenna. We texted back and forth and met outside the hotel we were staying at. From the moment we met on that sidewalk all the way to the hotel room, we were all over each other. The second we saw each other we kissed – just the two of us, alone in the middle of the night on an abandoned Austin street. It was passionate from the get-go. We flirted, touched each other, and kissed all the way to the hotel. In the elevator she plunged her hand into my jeans and gripped my cock. Once in the room, we ripped each other’s’ clothes off, her moving back toward the bed and me shuffling forward. She grabbed my cock again and asked if I had a condom. I didn’t. I threw on some shorts and went next door to see if any of the other guys in our party were more prepared. I walked outside and knocked next door. No luck. Then, just before I went back in the room where naked, beautiful Jenna was waiting, I was suddenly alone. I thought of Lucy – still at school, working away in the library, finishing all the hard work she’d put in. I missed her smell and holding her and I wished she was with me. In that brief moment of reflection, everything came to a grinding halt. Guilt washed over me, I went back inside, told Jenna I couldn’t find a condom, and the moment was gone.

That was the first time I cheated on Lucy. That’s right, there were others. But was it really cheating? Were we really together? We’d vowed affection in a very serious way many times, and we were unquestionably exclusive lovers, but who knows where we stood. And anyway, if self-destruction was what I was after, I’d wasted the moment. No relief, no satisfaction, no release. Just remorse. Jenna gathered her clothes, got dressed, and left without a word.

Everything in life is about sex, and sex is about power, but even more so, relationships are about power. When Lucy told me she was moving to Guam, I realized I had no power, and this was my way to get it back. It’s a pathetic, embarrassing, juvenile way of carrying on, but it’s still a way. Maybe Jenna was vindication for all the pain Lucy had put me through, or maybe I’m just an asshole, but the decision to cheat comes long before the opportunity, and I suppose I’d already made up my mind. I’d made up my mind that January day in Los Angeles. I’d made up my mind, because it seemed like she’d passively made the choice for me. After Jenna left, lying in bed later that night alone and half-drunk, I told myself that she was the first and last time. I still wanted to be with Lucy.

Or maybe it wasn’t that January day in Los Angeles. Maybe it was simply my carnal desires that caused me to stray. I flew home and started fantasizing about what it would have been like to be inside Jenna that night, and I wanted a do-over. I wanted a rendezvous. I started flirting with any woman that would give me attention. Curiosity. I wanted that porn star with those heels. I wanted at least someone else out of the 3.52 billion options. I wanted a threesome. And I wanted it with an Asian. Or maybe I just wanted Lucy to love me back. Who knows?

Ten More Weeks

If there was any doubt about whether or not we were still together when I hooked up with Jenna, one month later, Lucy came to live with me in Florida. She needed somewhere to stay while studying for the California bar exam, and I hoped that ten weeks with me in Tampa would be a turning point. And while Ten Weeks in Tampa sounds like a really bad romantic comedy starring Hugh Grant, I still had high hopes – like it would be some form of couples’ therapy. Then again, it was just as likely that things would fall apart and at the end of ten weeks we’d say goodbye. Either way, there seemed to be no option in between.

The couples’ therapy idea was hindered by my own hang-ups, because all the anger and resentment about Lucy moving to Guam still coiled and flexed under the surface of our interactions, and I essentially turned into a jealous, resentful maniac. I was too prideful to be honest with her and too hurt to be vulnerable, so I figured this was the last ten weeks I would get to be with her and I started to look for ways to malign her in my head. One evening we were walking together on the beach at dusk, and almost as though I had an out-of-body experience – like I was watching myself commit a heinous crime – I became incredibly interested in her sexual history. I asked how many men she’d been with. I wanted to know intimate details of every encounter. I wanted to know if she’d had a one-night stand, if she’d ever had a friends-with-benefits situation, or if she’d been in a threesome. Much to my surprise, she begrudgingly told me nearly everything. She’d only been with a dozen or so men. She only had one one-night stand, with a male model, which she did as vindication for being cheated on in college. He came too soon (ha!) and it was an awkward, brief encounter. Lastly, she had a friends-with-benefits situation in college, but grew tired of going over to his house and getting fucked because, in her words, she “felt like a whore.”

That last tidbit was exactly the salacious detail I was after. The masochistic urge to hear titillating and painful specifics about Lucy’s past lovers gave me some sense of relief – like it was okay things weren’t going to work out, because she had a murky sexual past. Or at least I needed to think that, and because I’d become a deranged nut-job, I made it a regular practice to pry into the sordid details of her life. It was like I was digging around in the basement of a murder house – I didn’t want to find a collection of corpses, but the curiosity of a cheap thrill compelled me.

Days later, on another sunset beach stroll, Lucy told me how in college at Emory someone tried to drug her. She was at a house party at the Atlanta mansion of former NFL quarterback and convicted dog-fight ringleader Michael Vick, and a sexually frustrated friend of Mr Vick’s took umbrage with the fact that Lucy turned down an offer of cocaine, which was openly being passed from the 30-something-year-old dead-beat hanger-ons to the 20-year-old coeds they lured to the mansion party. When Lucy refused, this unnamed man dabbed some on his finger and tried to stick it in her mouth. She recoiled, and people excoriated him, but instead of reporting him to the police or immediately leaving Lucy and her friends forgave him. As she recounted this, I thought about how stupid and shallow she was for going to the party in the first place. I wanted to believe she was some whorish drunk who lacked judgment and common sense for not reporting him or leaving the party. But getting stuck at a party with a perverted loser who thought assaulting a college kid was okay was more like college-aged naivety, and not reporting it could more be attributed to her pleasant, non-confrontational disposition.

I was looking for ammo to use against Lucy, but all these stories just made me sad – for her being caught in uncomfortable or compromising situations, for me not being able to bash the head in of every man that ever hurt her, and for humanity in general that a man would treat such a sweet person so wrongly. Sure, it was helpful at times to imagine Lucy being plowed by some pimply faced, sweater-wearing, Emory douchebag while she laid prone on an unmade bed with cum-stained sheets, and there was some small hint of satisfaction in that I knew she ‘felt like a whore,’ but I didn’t like thinking about her feeling used, and the more details and bad facts I gathered, the worse I felt. Masochist doesn’t even begin to describe what I was doing.

In the meantime I wasn’t such a saint, and for the entire ten weeks I couldn’t get the fact that she was leaving for Guam off my mind. Some people can pull off a long distance relationship spanning 8227 miles, but I’m not one of them, and I couldn’t take the fact that she voluntarily put us in that situation. I would imagine what her life would be like on that island, and how jealous I would be of anyone who got to hang out with her. I’d imagine the worst, with new versions of her ‘college whore’ scenario, and all the insecure delusions I had when we first met crept back up to the surface. Any comfort I felt early on in the relationship was completely destroyed by the thought of her leaving. The physical intimacy would be completely absent, given we’d see each other two, maybe three times over the next nine months, so instead of enjoying that last ten weeks and focusing on being a better boyfriend, I spent my time consumed with psychotic sex fantasies that stoked the fires of intense jealousy.

There were fun times. On weekends we would go to the beach, go on hikes around the swampy Everglades, and go to bars or have parties with the other young lawyers I worked with. But she wanted to learn to surf, and I never took her. She spent entire days alone in my little beach shack of an apartment studying legal minutia that make horticulture sound exciting, and I should have made our time together more thrilling. Maybe if I’d done more I would have never lost her, but I was too busy building my portfolio of damaging evidence. I turned things toxic.

When summer ended Lucy had to fly back to California to take the bar exam. As I dropped her at the airport I feigned optimism and said we’d talk soon, but it didn’t feel like ‘see you later.’ It felt like ‘goodbye.’ In my heart it was over, but I couldn’t let go, and if I was an obsessive, controlling head case before she left for Guam, it only got worse. For the next year and a half and we jostled back and forth between every relationship status you can imagine: Being exclusive, an open relationship, seeing other people, being exclusive again, seeing other people again. It was all bullshit. When she would willingly agree to be in an open relationship, I would secretly stew that she was really so very amenable to that arrangement, even though I asked for it. When I demanded that we be exclusive again, my blood would boil at her perceived indifference. I expected her to be excited that I didn’t want to fuck other people, instead she just shrugged and said, ‘okay.’ The Skype conversations were less than satisfying, and I missed her touch. In the end, sex matters, and we were so far away from each other. Then again, as crazy as I’d become and as lonely as it made me that she was so far away, it wasn’t until it was all over that I realized why this happened: I was in love.

Part Two: A Sex Rampage of Epic Proportions, Brought to You by Modern Technology

More Venery

Bob Bingham, a former executive editor at the New Yorker, died in his late fifties from a brain tumor. When asked by a friend what he’d missed or would do differently if given the chance, he thought for a moment and said, “More venery.” Mr Bingham, by all accounts a distinguished gentleman, an intellectual, and a member of New York’s elite, serving as editor for one of the world’s most renowned publications, nevertheless remarked on his deathbed that he wished he’d engaged in just a little more dirty sex.

In the 2006 indie-sleeper hit movie Little Miss Sunshine, the filterless grandpa, played by the fantastic Alan Arkin, turns to his 16-year-old grandson Dwayne and offers the following advice (Richard is Dwayne’s father):

Grandpa (to Dwayne): “…I don’t want you making the same mistakes I made when I was young. Dwayne, that’s your name, right? Dwayne? Listen to me, this is the voice of experience talking. Are you listening? Fuck a lotta women, Dwayne.”

Richard: “Dad!”

Grandpa (to Dwayne): “I got no reason to lie to you kid, fuck a lotta women. Not just one, a lot…”

At the end of those ten weeks with Lucy I drove away from the airport and felt a profound sadness unlike anything I’d ever felt in my life. The cure, I thought, was to follow Grandpa’s advice and fuck a lot of women. Lucy didn’t satisfy my every desire, and she’d left me anyway, so maybe fingers in buttholes, ramming my dick down a delicate feminine mouth, eating out so much box I became an expert on female anatomy – maybe that was the answer. I was open to anything, and with as many people as possible. I’d missed out on sex, so now was my chance to fix that problem. That’s what I did, and I did it in self-destructive fashion with no regard for anyone but myself, and I did it using swipe-apps.

But not at first.

After Lucy left for Guam, it didn’t take long before I fell into a weekend routine of going out to the local Tampa bars, getting blackout drunk, stumbling home to my little shack of an apartment, video chatting with her, professing my love for her, flinging wild accusations about the men she was sleeping with, dog cussing the shit out of her, professing my love again, more dog cussing, back to wild accusations… until I passed out in front of my laptop. She would patiently listen on the other end, and being 15 hours ahead she was usually just starting her day, and I can’t imagine what these brunch-hour phone calls were like for her. I assume that having a drunk, raving maniac who is also your boyfriend scream at you over a video link with the rhetorical logic of a schizophrenic is not exactly pleasant, and I’m sure I wasn’t helping my case for things working out between us. Getting blackout drunk was a desperate cry for someone else’s love, and crawling back to her when I struck out was a manifestation of how I truly felt. I missed her, and we were both too scared to sever our ties.

We hadn’t defined our shitty relationship, and I began to indiscriminately chase every bit of skirt in every meat-market bar in the Tampa area, and after a couple months of pin-balling around clubs and bars, spilling half my $10 cocktail while jostling through a crowd just so I could find out the girl I was eyeing from across the room had a boyfriend, I gave up. I can’t talk to women sober, so God knows why I thought I’d be any better drunk.

A year went by, and my relationship with Lucy crumbled (see Chapter five). After she came to her senses and told me in no uncertain terms to leave her alone, I became determined to fill the void she’d left, and I turned to the swipe-apps. It was fall of 2014, and Tinder had become the most popular dating service for millennials and beyond on the planet. I downloaded the app and the first couple of months were rough. After matching with only the hideously deformed or extremely overweight, I drew on the counsel of my Gay Friend James, he worked his magic on my profile, and around Christmas time I matched with Cindy.

The One-night Stand – Cindy

Tinder was called the ‘hookup’ app, so if I couldn’t figure out how to get laid with an app whose sole purpose was to get people to hook up, I might as well take a vow of celibacy, shave my head, buy a red robe, and move to Tibet to study Mahayana buddhism. It was just a few days before my first Christmas without Lucy – my first Christmas alone – and Cindy was home for the holidays from Tallahassee, where she was getting her M.B.A. at Florida State. She had red hair (collars and cuffs as it transpired), weighed about 110 pounds soaking wet, had a sweet, mischievous face, and a body like a 16-year-old-boy. Attracted to 16-year-old boys I am not, but desperate times call for desperate measures. Plus, Cindy was very feminine and charmingly pretty in her own way, and she appeared to have a lady-boner for me. I flirted with her over the app’s messenger function for a bit and then, because I was drastically lowering my standards anyway and felt I had little to lose, I asked if she’d like to come over. She said yes. I ran to the store to pick up alcohol, did a quick social media check to make sure her pictures weren’t fake and she wasn’t a serial killer, and an hour later she was sitting on my couch sipping on Bourbon and talking to me about blue grass bands she liked. Indiscriminate sex with a virtual stranger wasn’t something I was interested in until I got my heartbroken, but after Lucy I threw discretion out the window. I was a 30-year-old man who’d never had a true one-night stand, and this could be my chance.

The key to any early encounter with a female you’re interested in is to break the touch barrier as soon as possible. That’s because if a lady doesn’t want to be touched, she will let you know directly by saying something that indicates she might not be interested, like, “don’t touch me,” or by recoiling at the sight of you approaching her (this is what usually happens with me). At that point you will know that you might as well go home and jerk off while crying. And I want to be clear here – I don’t mean you should initiate contact in a Donald-grab-them-by-the-pussy-Trump kind of way, but rather in a light touch of the arm or hand or a graze of the elbow. If you do it too soon, you’re a creep, but too late and it adds a level of awkwardness that you might not be able to recover from. Remember, a tit grab or an ass slap just means you’re disrespectful and a sex criminal who should be prosecuted for assault, so don’t do that.

When I cozied up to Cindy on my couch after chatting for 20 or 30 minutes and grazed her arm during a heated debate about a band she liked, she looked me in the eyes and smiled. Five minutes later, we were making out. I asked if she wanted to move to the bedroom. She said yes. Two minutes later we were naked and I was pounding away at her tight little pussy, her moaning loudly to fuck her harder. It was sex with the vigor of a theatrical performance, and maybe that’s how one-night stands are supposed to go, but it was exactly what my depraved, blackened heart needed. My faith in humanity had been chipped away at by the only woman I’d ever loved, and I’d fully internalized the Jason Sudeikis/Zach level of ‘fuck it’ attitude. That would have been the ideal night to recycle that now classic Tinder meme – the one that even your mom knows: ‘Do you have vet insurance? Because I’m going to smash your pussy tonight.’

Before Lucy I always thought a one-night stand or sex with a stranger was dirty and cheap, and that it was too uncomfortable to fuck someone unless you had a deep emotional connection with them. Sex with a stranger didn’t work for me in the past because I was awkward, not because the experience itself was awkward. My puritanical worldview of casual sex was firmly behind me now, and I planned to fill the void Lucy left in my life with the entire populous of single female Internet daters, starting with Cindy. In that moment in my bedroom, it seemed like there could be nothing more natural than listening to Cindy scream out that she was coming as I lifted her hips up and let her ride my cock as I held her butt in my lap. When I pulled out, ripped the condom off and blew my load all over her stomach and barely-there tits and flat stomach, all I could think about was… nothing. I thought nothing at all. It was as though my brain emptied out at the same time as my nuts pumped that translucent white mess all over Cindy’s skinny body while she smiled up at me – a devilish, seductive smile. Sometimes, to get your mojo back you have to fuck a fire-crotch with the body of a 16-year-old boy.

She cleaned up and I laid there for a moment with no idea about what to do or say next, not being versed in the protocol of a post-coital one-night stand. Then she got up, put her clothes on, said goodbye, and went home. Easy as that.

Friends-with-Benefits – Amanda

Just days after I was plowing my dick into Cindy, I matched with Amanda. We avoided the awkwardness of a first date by meeting in a bar one evening after we’d both consumed enough alcohol to kill a small horse. She was tall, blond, with thick legs and tragic mosquito-bite tits. A Swedish girl from Michigan, everything about her was Nordic. She had a cute button nose, small face, thin lips, and blonde hair. She was a third grade elementary school teacher with a spicy personality and a coy, cute demeanor. Despite being almost six feet, she was proportional enough to still look human and somehow both clumsy and elegant, instead of just clumsy (which is how most tall girls are). I didn’t fixate on the fact that my breasts were larger than hers, because my standards had already plummeted through the floor, and I was drinking heavily enough on my Tinder dates to drown any reservations. (Protip: On swipe-app first dates, alcohol generally helps.)

I had just flown back to Tampa from a quick two-day trip to see my parents for Christmas, and Amanda was dressed as a Christmas tree. Halloween had been months before, it wasn’t a costume party, and she looked ridiculous, but at that point I would have fucked a Christmas tree if the hole was at the right height – a Douglas fir, a Norwegian spruce, or even a dry scabby shrub, so long as it was sort of feminine shaped, there was a place to stick my cock, and I was drunk enough. Plus she looked like a Christmas tree that might be down to fuck, so we made out a little at the bar, danced, and flirted for a couple of hours, and suddenly we were back at my place. It’s tough to know exactly when people make the decision to hook up, but sometimes you just know, and within minutes of walking in the front door to my apartment I was lying flat on my back looking at my popcorn ceiling, holding her hair back while she fellated me. Having the stamina of a 12-year-old always seems to be a benefit when receiving oral sex, because 1) they probably think they’re doing an awesome job, and 2) nobody actually wants that thing and its salty snot-like emissions in their mouth unless they’re paid for it. God Bless ’em.

The remarkable thing about Amanda the Christmas Tree was not what we did, it was the startlingly frequency and casualness with which we did it. After that first night, it seemed like almost no time at all passed before we fell into a remarkably familiar routine: I would text her, she would come over, we’d watch a little TV, and then we’d go in my room where we’d do a few variations on the same theme, all involving her blowing me and avoiding the inevitable mess on her face and in her hair. We did this for the next three months, with no pressure or expectations, no discussion of relationship status or the implications of our actions, and never any awkward conversations beyond the immediate job at hand, so to speak. We never went on a date, never got truly serious, and we pretty much had a mutual understanding of what the score was at all times. She drew the line at intercourse for some unknown reason (perhaps she was a post-op tranny with a lot of inflamed sutures), which was fine by me because I was receiving on-demand head.

What was she getting out of any of this? Other than a mouthful of cum every couple of weeks, I have no idea.

Did she want a relationship? She never forced that issue, and we certainly weren’t exclusive.

Did she just want a hookup? Yes. Obviously. But we weren’t having actual sex, so…

Was she just practicing her fellatio technique? Perhaps the most plausible, because she was certainly getting plenty of practice.

All told, she must have sucked my cock 40 times over the next few months, which I thought was pretty special. The only thing Amanda seemed interested in was my tiny little pecker in her mouth and my jizz all over her face. I’d never had such a purely transactional arrangement. The relationship ended just as you probably guessed – it dwindled off. The late night cock-sucking practice sessions became fewer, we talked less and less, and we drifted apart like unmoored rafts in the wide ocean, soon out of sight. I missed our periodic hookups, I missed her goofiness, and I missed the enthusiastic blowjobs. Then again, I didn’t miss them too much, because there was plenty more to come.

The Tattooed Hipster – Sky

First it was Cindy and Amanda, then a gypsy ho whose name I can’t remember, a Florida University law student named Catherine (or Kristine? Or Kirsten?), there was Nolan the yoga instructor, a breastaurant employee named Alexandra, a Tampa Bay Bucs cheerleader named Marisa, and then there was Sky.

I’m a pretty straight-laced dork, and that’s probably why there has always been something alluring to me about the hipster universe. Hipsters try so hard to be different that they all end up looking the same, but they also all have that same I-don’t-give-a-fuck confidence that I admire in people like Zach and Jason Sudeikis, it just comes from a different place. With hipsters, you’re never sure if they’re going to steal from you, bake you some gluten-free bread, or engage you in a protracted (albeit totally misinformed) political discussion. So when I went hunting for a hipster, I wanted a woman with skinny jeans, tattoos, and a grungy style who liked to hang out in dive bars and whose friends worked blue collar jobs. I wanted a woman who thought she was a notch above the rest of the world because she shopped at thrift stores and who was pretty, not because she was porn star hot or classically beautiful, like a model or an actress, but because she so thoroughly embraced her counter-culture lifestyle that her beauty could best be described as ‘wild.’ That’s what I was looking for.

Sky was exactly that. She had a full sleeve tattoo on one arm and a giant tattoo of Vishnu, or some other Eastern religious character that she probably knew nothing about, running just below her right boob and down to her hip. Her teeth were just slightly spaced apart, giving her smile an exotic uniqueness. Her hair was dyed with blonde streaks, she wore too much makeup, and on one of our first dates she wore a raggedy white faux fur coat that looked like the matted hide of a wet polar bear. She had enormous double-D tits, phenomenal legs, and an elegant dancer’s body. I was catching her on her way down, and even though she was still smoking-hot, you could tell she was clutching onto her once insanely good looks, with her boobs sagging just a little bit more than when she was 20, and the naturally accumulated fat of age just starting to round her waistline.

The potential for incredible sex with Sky was evident immediately. The first time we hooked up we were sober enough to know exactly what we were doing, but just drunk enough to not hesitate in doing exactly what we wanted. We went to dinner and then made it back to her place downtown. I walked up the old creaky wooden stairs of her two-bedroom apartment and sat on her old thrift-store couch with her disgusting rat-dog Luna. Sky poured us drinks and came and sat with me. After I kissed her, we stood up, and with our lips still locked and our bodies dancing together, we shuffled into her bedroom while ripping off each other’s clothes. I laid her on the bed and paused for a moment, looking down at her naked body. Her tits were tremendous. All natural and perfectly symmetrical, they hadn’t totally given way to the forces of gravity, and barely fell off to the side when she laid down. I got on top of her and we made out some more. Foreplay on foreplay after foreplay. I touched her gorgeous body all over. I wrapped my arms under her legs, lifted her hips up, and slid deep inside her. As I entered her slowly, her entire body shook and shuddered with orgasmic pleasure. She moaned in a helpless whine as I slowly started fucking her. Things continued to escalate. I fucked her sideways, I turned her on her stomach and did her doggy style, picked her up, did her missionary again, then turned her back on her stomach, driving my dick deep inside her. We fucked like stuck pigs that first night, and that pace of gymnastic sex never let up.

As we laid next to each other spent, she confided that it’d been a few months since she last had sex, but based on her orgasm, her seizure-like shudder when I first entered her, and her enthusiasm, you’d think it’d been years. It wasn’t just that Sky was great in bed (and she really was great), she also had the sassy charm you’d expect from a jaded hipster. Her friends were all covered in body art, they all lived in dilapidated buildings, they all previously worked or were still working in the service industry, and they all had two or three mangy rescue dogs whose vet bills they couldn’t afford. I loved it. I would show up to a group gathering with my ‘Standard White Guy’ uniform and my short, clean-cut haircut and ink-less body, doing my best to play it cool and fit in. I was a Navy JAG in a world of drug-using counter-culturists. While slightly intimidating, Sky’s crew was cool and accepted me – I didn’t get a bunch of tats and change my wardrobe, but for the short time I was sleeping with Sky those people were my friends.

I used to view promiscuity as only a negative, but unless you’re sleeping with the woman from the ‘orgy sex party with the football team’ scenario, or her vagina has been completely and irretrievably ruined by hundreds of cocks over the course of her young life, there’s nothing wrong if she knows where to go, where to touch herself, where to touch you, and how to get everyone off in the most mind-blowing way possible. That in a nutshell was Sky.

Before this post-Lucy sex rampage, promiscuity mattered so much to me that if I even thought a woman was a slut, I’d run for the hills. Can you blame me? It’s not fun for anyone involved if you pair a pencil prick with a slack pussy. I’m looking out for everyone here. It’s easy to tell when a woman has been ridden like the town bicycle, because either her vagina is stretched out so far it looks like a week-old roast beef sandwich or they know exactly what they’re doing – like bouncing on your dick in reverse cowgirl with the focus of a serious athlete. Sky had shades of both, in that her cunt was of the quality that you’d expect from a 30-year-old super-hot hipster who used to bartend downtown – she clearly got around. Yet fucking her was like a Disneyland adventure ride that I didn’t want to end, because she knew exactly what she was doing.

I will never forget one night we went back to my place after dinner and she started blasting Van Morrison at full volume. We were already a little drunk, and we danced around naked in my living room with beers in hand. We started kissing. Then touching. I massaged her clit and got harder and harder. I spun her around, bent her over my kitchen counter, and started fucking her from behind. Minutes later I had to pull out because I thought I was going to blow my load. I took a step back for a short break. Then, without any warning or instruction, she spun around, dropped to her knees, and put my entire cock in her mouth. Holy shit could Sky suck a mean dick. There is nothing better than an enthusiastic blowjob, and Amanda the Christmas Tree could have used some pointers from Sky. My eyes rolled into the back of my head, and I let this beautiful fellatio demonstration continue for a couple of minutes before I started to blow. In what seemed like the only appropriate thing to do, I pulled out of her mouth and stroked myself to full climax. She tilted her head back slightly and pursed her lips, glancing up alluringly to receive what I was about to give her. The white, viscous fluid splashed out onto her face and hair. With cum splattered across her nose, eyelids, and lips, she added a couple more deep-throated sucks on my cock, and my whole body shuddered. For a moment, my soul felt empty, and before she got up to go to the bathroom I looked down at the mess on her face with a twinge of disgust and thought, “Well, there you go… is this what you wanted?”

But the moment quickly passed. Sky needed to clean up, and there were more women to fuck. There were more adventures to be had. I was just getting started.

That was a typical Tuesday night with Sky, and of all the post-Lucy nymphs she was the most fun. A combination of interesting, scary, and erratic, she was also sweet, friendly, and not totally insane. She had a worldly view, great self-awareness, and she certainly knew her way around a cock. She was resourceful. Like many hipsters, she overcame her mediocre education by leveraging her somewhat manipulative personality into a solid job in medical technology sales. She was unpredictable (see the above story). She was sassy and had a strong personality, which always kept things interesting, even if it meant we got into some pretty heated disagreements because ‘sassy’ and ‘strong personality’ really meant that sometimes she could be a real fucking bitch.

Brandy Brunette

I was riding high on the confidence of fucking a tall gorgeous hipster who wore faux fur dinner jackets, so one night while I was out with my friend Scott and a feisty little brunette walked up and said hello, I knew it was on. Brandy had brunette hair and was a short, sweet, 26-year-old bubbly ball of innocence and joy with a fantastic ass. Always dressed like she’d just stepped out of a Saks Fifth Avenue catalog, Brandy had the well-manicured face of someone who had the money to make sure she always looked her best. We went out on a couple of dates and kept things very PG, because even though I like to let it be known right away that I’m a sexual maniac, I could tell she wanted to take things slow.

My Gay Friend James’ birthday was coming up, so I invited her along. She said yes but asked if she could invite a friend who’d recently gone through a breakup, and I said sure, but explained that James would most likely not be interested, being that he prefers men. It was a date. Scott, his girlfriend Jennifer, James, and I waited at a fancy downtown restaurant for Brandy and her mystery friend. When they showed up, my jaw hit the floor, and I realized that Brandy Brunette had violated the number one rule in swipe-app dating: She brought a much hotter friend. Also named Brandy, Brandy Blonde was drop dead gorgeous, with large, firm C-cup tits, and a curvaceous body that she tuned up daily at the local Pilates class. She was a sweet, sassy Southern girl – a ten – the most perfect blend of refined woman and pure fuckability. If I didn’t change tactics, imagining Brandy Blonde’s body was going to haunt me forever.

After dinner I talked with Scott and Jennifer about my new plan: Brandy Brunette was out – I was going to make a play on Brandy Blonde. Jennifer, who was always the good sport, could see the desperation in my eyes, and after reminding me that I was definitely going to hell, she reluctantly agreed to run interference. After a few more drinks and a round of shots, Jennifer pulled Brandy Blonde aside, and explained that I was really interested in her and not Brandy Brunette. We were never sure if she was legitimately exasperated or just being overly theatrical, but she almost fainted. This was not the first time this happened, she said, and she couldn’t do it to poor Brandy Brunette again.

Well, that didn’t work.

Plan aborted. I found Brandy Brunette, whisked her off into a corner, and we started making out. An hour or so later I was in the reclined front seat of my car while Brandy Brunette bounced up and down on my cock. Somehow recovered from this tragic scenario, Brandy Brunette moaned in delight and gyrated her hips back and forth on my dick. She had the nicest snatch since Lucy, and regardless of how drunk I might have been, I thought this might be something that could last. Then again, we’d been on two dates, so I didn’t have the clearest picture of what her personality was like.

The next morning, we negotiated the guilt she was feeling about fucking me in the front seat of my car. You see, I was only the fifth man she’d ever been with, and she was hoping to save herself for marriage. Brandy Brunette was the kind of born again Christian I could deal with – she’d been ‘born again’ five different times, each occasion vowing that she would not have sex with her next boyfriend until she had a ring on her finger. Explains a lot about your perfect pussy, you’ve only had sex with five people, I thought, as she explained how important her relationship with Christ was to her. But apparently once the seal was broken with the man she was with, it wasn’t the amount of sex that troubled her, it was the number of guys she was with. Music to my ears. We boned like sweaty teenagers over the next few months, screwing every chance we got. God did I love sleeping with her. She was the tiniest little spinner with the nicest vagina and a smoking-hot body. She wore yoga pants prodigiously, always smelled nice in the tempting, feminine way that girls who know what they’re doing always smell nice, and she absolutely loved to fuck, religious confusion not withstanding.

As far as ingredients needed to create sexual napalm, a magical vagina is a key component but it’s not everything. Something about fucking a small women is a huge turn on, and Brandy Brunette was five-foot-three and maybe a 110 pounds, which meant I could go from a reverse cowgirl, to doggy, to missionary, and back to cowgirl in the blink of an eye, flipping her over, spinning her sideways, propping her up on my dick, and pile driving her tiny little pussy while she squealed in delight. And squeal in delight she did. She loved it. If there was one female genitalia that was perfectly designed for my tiny Oscar Mayer weiner pencil dick, it was Brandy Brunette’s. I would get hard just thinking about her tight, pristine vagina that stayed perfect due to good genetics and resisting the urge to let any random dude plow her at will.

Not everyone is so lucky to be blessed with the good genetics of a perfect pussy, but there are a lot of different strategies for women to improve things downstairs – even if you’ve gone through the horrific process of childbirth. Take if from my friend Will.

Post-coital with a Vegas prostitute who had a boyfriend and had given birth to her child vaginally (Will is a very curious person), she explained that despite getting fucked for a living, she was able to maintain a very nice vagina above and beyond because of one reason: She worked at it. She exercised, she told him. Kegeling works, and she did it not just for herself and her clients, but for her boyfriend as well. If there’s a Vegas prostitute out there who gave vaginal birth but who still has a nice pussy, it seems like there’s not a lot of good excuses for having jerky lips that look in need of extensive labiaplasty. If there was a way to make my dick bigger I would do it, so unless you’re dating a male porn star or a professional basketball player, it’s probably worth it to put in a little exercise. Your man will thank you.


There was Sky and Brandy, and there was the Florida State Senator’s wife, the police officer’s daughter, the yogurt shop employee, and the airline stewardess. The swipe-apps were working. I wish I could tell you that Lucy was a distant memory, and that all these women were enough of a distraction to keep my mind off missing her. They weren’t, and I longed for something more. I’d been in Florida a little over two years, and I was getting more pussy than I’d ever gotten in my entire life, but I started to tire of the vapid routine:


Flirt via message

Exchange numbers


Set up a date

Meet for drinks

Kiss them goodnight

Arrange second date

Make out

Have sex


My scorched-earth strategy of dating everyone and anyone as I counted down my time in Florida reflected my life circumstances – I knew I was leaving and probably never coming back, but I also yearned for something real. Banal sport-fucking is a lonely hobby despite the hookup part of it, and I started to think that maybe I wanted a girlfriend. This whole sex rampage experiment was starting to feel less like a conquest and more like a descent into madness – a corruption of everything good I once had in my life, and riddled with painful reminders of all the things I’d done wrong in my relationship with Lucy. I thought moving to California would be a fresh start.

Not quite.

In June of 2015, the Navy sent me back across the United States to the West Coast to Oceanside, California, a small city north of San Diego and southeast of Orange County. I had so much momentum and for the first time in my life I was getting a lot of sexual attention from women, so I felt like I had to take advantage. Plus, there was an entirely new pool of West Coast women available. There was Megan the doctor, Cherish the vice-president of a local bank, Hannah the MMA fighter, Lily the au pair, and Filomena the law student. (That’s right – I fucked an MMA fighter. Shit was getting weird at this point.) The best part about the women in California was that they all seemed to lose their goddamned minds in the sack. My paralyzing sexual inadequacy was long forgotten, and while I want to believe they enjoyed it because I’d become a good lover, I knew that couldn’t be it. Maybe they were all faking it? Certainly seemed like the most plausible explanation to me. Whatever. I didn’t care about their reasons, because I was having a string of great sex with a seemingly endless number of beautiful women. There’s nothing worse than being a sex addict and a terrible lay, and prior to this glorious stretch of fornicating I always seemed to be both. Before I started Not Giving a Fuck, my after-sex routine included apologizing, counting the seconds between awkward silences, and hiding my head in shame. Pretty much in that order. If I should be so lucky to have one time in my life when women wanted to fuck me, and if this was indeed that time, so be it.

Then I was on the phone with Will one day, and he called me out. He said I was a sex addict, and the screen shots from the swipe-apps, the string of kiss-and-tell stories, and a 20-question sex survey he downloaded off the Internet seemed to confirm it. Maybe he was right, and I started to think about the last few months. All the different women and all the deviant sex acts I thought I wanted just seemed too damn complicated. I was tired, and I was determined to change. I wanted to find someone I could spend a Sunday night with watching Netflix, who I could buy a dog with, and who I truly cared about. I also couldn’t watch another girl, a few weeks into screwing each other, bawl her eyes out after I explained to her I wasn’t interested in a relationship. I had the momentum of knowing how to score with chicks, but the momentum of misanthropy driven by getting my heart broken had all but worn off. I had hope, and I thought I found what I was looking for when I matched with Alyssa.

At least I thought so.


Her profile only had one picture, and it was the hottest profile picture I’d ever seen. Golden, shoulder-length hair. Green eyes. Innocent, kind smile. A beautiful Southern belle of a girl. She was a 33-year-old medical resident from Houston, Texas. Beauty and brains. Could I make her my girlfriend? As if I could be so lucky, I thought. But there was only one photo so I worried she might be fake, and she looked more like 25 than 33, but I thought, maybe she just takes good care of herself? We matched during one of my visits to San Diego to see college friends, and the first night we planned to hang out she cancelled dinner and asked if I wanted to come over instead. Seemed like a bold move for a woman to make on a first date, but I at least knew one of us wasn’t a serial killer. And her explanation made perfect sense: She was a busy doctor who had to be up in the morning for rounds at the hospital. So I thought what the hell and agreed.

A dog is always a good ice-breaker, and Alyssa met me on a street corner outside her apartment carrying her cute little purse mutt named Stella, who was friendly and energetic. We played with the dog, she invited me inside, offered me a drink, and we chatted for a bit. She was funny, smart, sassy, and bitchy in a playful way. She talked a lot about the practice of medicine to the point where it seemed obsessive, but I suppose being a doctor requires a degree of obsession. She was training to be a urologist, but ultimately wanted to specialize to be a kidney transplant surgeon. Talking with her about medicine was fascinating, and even though it often seemed to be the only thing she talked about I liked that she was ambitious.

We had a couple more drinks to diffuse the tension and she put on a movie, instructing me to lay down next to her. As we spooned on her couch, I started to get really turned on. Her body was incredible for a 33-year-old, with long, slender arms and large, perfectly shaped tits. Laying behind her, I brushed her hair behind her ear and started to rub my hands all over her body, gently lifting her shirt and stroking her bare skin just about her hip. As I did this, she started grinding her butt against my cock, scooting in closer to me. Pretty soon I was predictably rock hard, and she moaned pleasurably when I kissed her neck. I got on top of her and we kissed. Things escalated and clothes started coming off. I wasn’t sure if we were just going to sexually frustrate ourselves or if she would like some kind of release after what was turning into a lot of foreplay, so I asked if she wanted to go upstairs. She said yes.

Naked, I could see she had voluptuous Kate Upton-like tits. She was five seven without an ounce of fat on her body, and she had the figure of a runway model. I found a condom, put it on, and slid inside her. At her request, I fucked her hard, missionary style, and then she told me to fuck her harder. Yikes, I thought. Here we go! I did her doggy style until finally she asked to get on top. She did, and grinded away, moaning pleasurably until she announced loudly, “I’m coming! I’m coming! Oh! Fuck-fuck-fuck-fuck-fuuuuuuuuuck!” After I came shortly after, she rolled off me and reached for Stella, who I hadn’t realized was sitting on the bed and shockingly close to us. I was surprised that this little half-terrier, half-Chihuahua dog was practically in on the action, and Alyssa was paying her outsized attention considering I was just lying there. Sort of weird, I thought. But then again, I just had sex with a hot doctor within 40 minutes of meeting her, so the whole situation was a little weird. I wasn’t about to complain. We made some small talk after the sex and got ready for bed. She had work in the morning, but wanted me to stay, which was unusual, so I did. We fucked again early the next day, and I figured I’d found my new girlfriend. This has potential.

As I left the next morning I had the passing thought, Should I be concerned? We barely got past introductions before I was pumping away at her. Nah, it’s 2015, I told myself. We’re adults. Alyssa the hot doctor seemed to be everything I was looking for, so what was the catch? As we hung out over the next few weeks, I figured out exactly what the catch was – she was batshit fucking crazy, and first impression aside, there were all kinds of problems that I worked very hard to ignore. First of all, her vagina was so blown out I felt like I was thrusting my weiner into a warm apple pie, not an orifice designed for intercourse with male genitalia, even one as small as mine. This wasn’t Brandy Brunette’s tiny little beaver clamping down on my tiny tool. Even Sky’s abused pussy seemed like a 20-year-old virgin’s next to Alyssa’s smashed-up box. I convinced myself that sex with a blown pussy is still sex, so I figured I could get past it, but she was also not good kisser, or at least we weren’t a good team, because our chemistry was all over the place. Then she admitted her profile picture was five years old, and in the light of day I realized that time had done her no favors. Without expertly caked on makeup, she looked ravaged, like a methamphetamine addict who slept an average of three hours a night. Her hair was stringy and thin. Her eyes were sunken. Her skin was pockmarked and scarred. She looked haggard, but she did have good tits. Then she told me something that explained why she might look like a meth addict – she’d been abusing Adderall since her second year of medical school. She’d take it late at night to write papers and then drink heavily to help her sleep. She’d take it any time of day, and well over the recommended dose.

Alyssa wasn’t just a bad kisser with a derelict snatch who was eight years older than her profile picture, she was also a prescription drug abuser, and it started to become clear that she was the kind of person who had been doing whatever she wanted, whenever she wanted, with whoever she wanted her entire life. But I still couldn’t let go. She was so good on paper, and I was so desperate for someone smart and interesting. I couldn’t let her go just yet. The next weekend we hung out again, and before we left for dinner I read one of her medical journal articles. I was half-trying to impress her and half-trying to see if she really was as accomplished as she claimed. At dinner she made a snarky jab at me, and I made some stupid, childish comment about a misplaced comma, and regretted it immediately. She called me out, I felt bad, was put on my heels, and she did everything to make me feel like I was wrong. She said it was no big deal, but spent the rest of dinner looking at pictures on her phone of her younger self. As she looked through the pictures, she ordered drink after drink, and it didn’t take long before she was pretty wasted. I’d had enough of her staring at her phone and ignoring me, so I got the check and walked out into the brisk San Diego night air. I had invited friends to meet up at the bar across the street, so I figured we’d get a couple drinks there before going home, and I would never see her again.

Then, out of nowhere, she fell out of the restaurant and started crying. I asked what was wrong, and she dumped an emotional garbage truck of baggage on me. She told me about how her mother committed suicide when she was 20, how her father is a vicious alcoholic, how she doesn’t have anyone in her life, how she’s scared to grow old and alone, how she was worried I was going to ‘fuck things up’ between us, and how people always abandoned her. She started to get hysterical, and brought up my snide comment about the misplaced comma in her article over and over again. While she choked back tears and I averted eye contact with passersby, I stared at this crumpled, gorgeous mess before me and wanted to run. She needed serious, professional help, and her story was so tragic, but I should have turned on my heels, ordered an Uber, and got the fuck out of there. Instead, I consoled her and told her it was okay. She seemed so pathetic and small, despite her harsh and intimidating veneer, and after a few minutes later of convincing her over and over that I would not ‘fuck it up,’ she dried her eyes, and we went to the next bar. I was just glad she’d stopped crying.

By the time Brett and his girlfriend Liz showed up to the outdoor bar we were at, Alyssa was completely fucking wasted. Then, as I was chatting with Brett and Liz, she started pleading very openly and loudly for me to fuck her in the ass. She bit my ear, sat on my lap, put her arm around me, licked my face, and whispered about how she wanted a threesome, how she wanted me to fuck her in the ass, and about how she wanted me to be aggressive with her and cover her in my tepid alcohol-infused baby juice. To deal with the histrionics of the night, I was pretty drunk myself at this point so I didn’t fully comprehend how insane this all was. We paid our bill, made our excuses, and 20 minutes later we were two people fucking with something to prove. Like the foggy haze of an orgy, I was ordering her around in various positions while she screamed out for more: Missionary, sideways, my dick in her mouth, my dick in her ass, my dick in her pussy, my dick in her armpit – I fucked her every which way you can imagine, and then some other ways for good measure.

“Give me that fucking cock,” she instructed like a deranged hooker. “Fuck me in the ass! Ugh! Ugh! Fuck! Me! Yes!” She was a broken husk of a woman with daddy issues and no gag reflex, and I was delighted to be a part of her sexual debasement. I can’t imagine how the neighbors felt about all this.

Just when I thought things couldn’t get any weirder, as I was flipping her from doggy style back to missionary, she turned around and punched me in the face. As in, with my dick still deep inside her, right in the middle of sex, she punched me in the face. I stopped thrusting and looked at her with legitimate concern. “Are you okay? Did I hurt you?” I said. She looked back at me with glassy, vacant eyes. “Keep fucking me,” she ordered, as if cold clocking me in the middle of sex was a perfectly normal thing to do. I rolled her on her stomach, stuck my dick in her asshole, and pounded away until I pulled out and blew my load on her spine. When I recounted the evenings’ sex-capades to her the next morning, she shrugged, smiled a coy, innocent smile, and told me that sometimes she does crazy stuff when she’s drunk. NO SHIT!

What was I to do? What I should have done was pack up my crap and get the hell out of there. Again – this was a chance to be free, to escape the madness. But I was daydreaming about all the weird deviant shit we were going to start doing in bed latter on that day or next week or whenever, and I figured this would be my one last hurrah before I really got serious and looked for someone to be with properly. I’d finally found a psychotic nymphomaniac who might be into all the perverse shit I dreamed about, and it was probably now or never. I’d just fucked her in the ass, she punched me in the face, and I wanted to try it again. It was going to be an experiment – a crazy, interesting experiment like the way reality shows about dating are an experiment: You want to see what’s going to happen next.

Alyssa tapped into every self-destructive tendency I’ve ever had, and she would later explain to me why she liked anal so much: It’s exciting because you’re not supposed to do it. And even though she was right, that statement pretty much summed up Alyssa’s life. Deviant sexual acts not traditionally reserved for polite society provide the same kind of rush as shoplifting, and Alyssa wanted each moment of her life to give her that rush. Sadly, I think she was realizing how unsustainable that life was, and how you end up with labial walls flapping outward like a sloppy deli-style pastrami sandwich and the complexion of someone who’s been up for three weeks straight. Once I ‘accidentally’ unleashed a rope of cum directly into her haunted-but-grateful eye, and rather than flinching in shock and horror and berating me she actually said “Thank you” and then went quietly blind for the rest of the night. She woke up the next morning with an eye that looked like an inflamed ball of fire, which apparently is not a good look among the staff in a hospital.

I was hoping to find a smart, beautiful, classy doctor, instead, I’d found a sex-crazed, alcoholic, drug-addicted maniac. The sex got crazier and crazier, and so did she. I never knew how many men she was sleeping with, or what venereal disease I might be subjecting myself to. Once, right after sex, she told me she forgot to take her birth control, she’d frequently tell me she was late on her period, and even took a couple of pregnancy tests. Yes, I would fuck her without a condom, because in the beginning she told me we were exclusive, that she was on birth control, and that she’d never have a baby as it would jeopardize her career. After enough bullshit, I learned my lesson and started wearing condoms. Pretty soon I was sticking my finger in her asshole, then we were using toys, then fucking in weird locations, then doing all these things at the same time.

Four months into our relationship we were texting one night, and she was telling me how she wanted me to cum on her face and then suck me dry. She told me how I could do whatever I wanted to her and she would do it, and that she wanted a threesome with a tiny girl with big boobs, and how she wanted to watch a girl suck my cock. She asked me what the weirdest, sickest, strangest thing I wanted to do was, and then told me she wanted to do it with me. I wanted to tell her that what I really wanted was a nice, pretty girl with an unbattered vagina that wasn’t all gross and splayed out, that I didn’t want to bring in other people, that I didn’t want someone who’d been fucked by a hundred dudes, that I wanted someone emotionally well-balanced who had a wide-variety of interests, and who was okay with a nice quiet night of normal sex, and then maybe watching a movie with a mug of warm cocoa. I wanted to tell her that I wanted a sweet wife and a happy family, a house in the countryside, and a partner that didn’t always require that I fuck her in a grandiose and theatrical style. Instead, when she asked me to describe what I would do if we had a threesome, I told her I’d fuck her hard while the other girl played with her clit. I had basically reverted back to having the emotional maturity of a teenager, and she lapped it up. You gotta love the self-harmers, if only briefly.

Alyssa was crazy combative, volatile, manipulative, but also so wild in bed that she was like a drug. While hanging out with her, it crossed my mind more than once, in a frightening and shocking way, that she was responsible for caring for and treating patients in a hospital. I thought about reporting her numerous times, but she was widely heralded as a widely heralded at being brilliant at what she did, had been published multiple times, and had a good reputation among her peers. What was I going to tell the medical board that she wasn’t fit to be a doctor because she was a psycho addicted to Adderall and obsessed with getting fucked in the ass?

Finally, and somewhat suddenly, I decided I wanted out. I wanted to flee for my life. I wanted to delete her number and never talk again, and I wanted her to leave me alone. I saw all the red flags and I ignored each and every one, because a wild sexual encounter is like a good hit of cocaine. Maybe Alyssa wasn’t the only drug addict, because I was hooked on her and she was the best hit I’d ever found.

Chapter Five

Part One: Love

The Little Things

Falling in love is mysterious because it’s something that happens without you realizing it. You meet someone, memories and experiences pile up, and all of a sudden you’re doing things lovers do that used to make you want to vomit, like texting each other heart emojis or calling each other stupid fucking pet names. The cliché that ‘words can’t describe’ what love feels like is one of those clichés that might be overused, but only because it’s so true. Because I met Lucy in my late twenties and I’d never been in love before, I missed the normal trajectory of adolescent hijinks where you experience the intense, deep, raging hormonal attraction of a First Love. And because of that, I didn’t have a trial run at doing things like saying ‘I love you’ and meaning it, or going through the whole process of getting comfortable with someone. After I fell in love with Lucy, it was like nothing existed before her, and because I hadn’t experienced that feeling, I was all the more vulnerable to silly vouches of affection. When I fell in love, I fell hard.

The First ‘I Love You’ and the Last

There are milestones in relationships that are difficult to navigate: When to Define the Relationship, How to Celebrate Birthdays, What to Get Your Significant Other for Valentine’s Day, and perhaps most importantly, When to Say ‘I Love You.’ From reality TV shows, to gossip columns, to self-help books, to high school hallways, everyone has an opinion on when to say those three loaded words. Some will drop the L-bomb at the one-month mark, preferring to expose their vulnerability early and hope for the best. Pre-teens will drop it casually, before they know exactly what they’re saying, like after a particularly nice kiss or an exciting new sexual encounter – pretty much after any rush of blood to the head. Adults, especially the hard-hearted and cynical, might wait until it makes fiscal or social sense to start operating in each other’s intimate worlds, which could be months, years, or never. Timing is different for everyone, I suppose, but I always felt that saying ‘I love you’ should mean something.

The first time I told Lucy I loved her, the words came tumbling out of my mouth, and the exact moment is as clear to me as the first day we met. It was the summer of 2011. We were at the gym around noon, taking a break from our summertime jobs working in the library, her as a research assistant and me doing appellate criminal defense work. For our midday workout routine, she usually ran on the treadmill and I lifted weights, and I always finished slightly before her. That day was no different. I was sitting on a plyometric box in the small outdoor courtyard of the Student Recreation Center at USC, watching people stretch, jump rope, lunge, and throw medicine balls back and forth, when she walked outside to meet me.

“Hey,” she said.

I looked up. She was standing in the sunshine, the light sweat glowing on her skin, illuminating her golden blonde hair and lighting her face. She wore a sweat-stained white A-shirt, black spandex shorts, battered old running shoes, and low-cut socks. I loved that she never worried about how she looked when she worked out. She was no-frills gorgeous, captivating without needing window dressings. I remember thinking that if someone looked that incredible wearing a sweat-stained A-shirt after working out in the hot summer sun, she must be the most beautiful person in the entire world. Then I realized she was, and all at once I realized how much better my life was with her.

“Why do you have that weird look on your face?” she asked.

I just kept looking at her, the wheels turning in my head.

“Let’s go,” she said, rolling her eyes and tapping my head playfully as if I was mad.

“Hey,” I said.

Before she turned, I put my hand on her hip to get her attention. And then the words just came out:

“I love you.”

Her jaw dropped and she paused for a long moment. Then she said, “Oh, honey. I love you too, but this is kind of odd timing.” And it was, but at that moment I absolutely knew for sure that I was speaking God’s own truth and I needed her to hear it. I know I should have waited for a more intimate setting, perhaps when she was wearing an evening gown at a nice dinner or a fancy concert; maybe on Valentine’s Day, or her birthday, at Christmas while exchanging gifts, but while I looked at her standing there in the sun, it was like the entire world faded away and she was all that mattered to me. The feeling washed over me, and as good as it felt to say those words to her, it was even better to hear them back – like a validation that I was worth it. Maybe I’d save the big production for a wedding proposal, I thought.

Saying ‘I love you’ raises the stakes considerably, and after I said it and meant it, I realized why people pronounce their love at the altar – the romantic love you feel for your partner instantly becomes more intense. From that moment forward all the wonderful feelings I had about her became magnified. Maybe I botched the timing, but there’s no formula for love and it was my first try and for the rest of that day I felt infinite.

Getting to Know Her and Falling in Love

That first summer was the summer of weddings. Two weeks after that first ‘I love you,’ Lucy and I drove up to Redding to celebrate my sister’s impending wedding with a family get-together. She had decided to marry the Frenchman after all, and Lucy and I hiked around the golden wheat fields near Shasta Lake, visited local swimming holes, ambled along creeks that cut through the dry valley landscape, and had noiseless sex in my parent’s guest bedroom late at night. With my family, she was her demur, shy self, but people saw in her what I saw in her – the obvious and startling beauty, but also the sweet, gentle disposition and sharp intellect. Three weeks after that we traveled to Long Island for Sarah’s wedding, featuring the Hawaiian-born love triangle of Sarah, Denny, and Quinten, and the uncomfortable night cap in her parent’s living room. Back in L.A. toward the end of the summer we made the short drive south to Orange County where my college friend Craig was getting hitched.

Maybe at a different stage of our relationship all these weddings would have translated into pressure, but my relationship with Lucy was just fresh enough that sharing those special moments only strengthened our bond. Plus, even though it was so early on and the relationship was still so very fresh, the idea of marrying her had crossed my mind more than once. That summer’s wedding circuit may have presented a false sense of reality, because life is not a series of endless parties. It was like being on a reality TV show where contestants are flown to the top of an epic mountain in some tropical locale where a four-course meal and a hot tub awaits. But it was a wonderful start, and by the end of the summer she was my best friend. We were a team, and we could take on anything together.

Before the 2011–2012 school year started, we did a trip up the coast to Carmel-by-the-Sea, Monterey, and San Francisco. Lucy loved to travel, so I took her everywhere I could afford. For Thanksgiving we went to Santa Barbara. I took her whale watching and we rode bikes along the boardwalk. When the semester ended we visited her family for Christmas on Long Island. We walked her dogs around the east neck of the shore, through the wealthy neighborhoods of the East Coast elite, pretending we were first time buyers, marveling at the old-money renovated palaces and quaint little Victorian homes, laughing at the boring, silly old people that lived in them, and knowing that we’d never be boring or old. For spring break we went to the Grand Canyon. We stayed in a hotel right on the rim of the chasm, hiked during the day, enjoyed nice dinners, slept in, made love, and took pictures of the wildlife.

In October of 2012 when Hurricane Sandy ripped through the Eastern seaboard, we hunkered down in her little apartment off B Street in Washington D.C., watching the storm outside. The streets were empty and flooded, and we watched the catastrophic weather with excitement and muted terror, feeling safe with each other. We laid in bed all day and saw the streetlights sway in the violent wind, the gutters overflowing with Biblical rain. Her old, dilapidated apartment building could barely handle the storm, and water poured in through cracks framing the large window that looked down on the street. I caulked the cracks shut as the water soaked the carpet and we laughed together at the chaos, marveling at the violent rain that ebbed and flowed in its intensity. It felt like we were the last two people on Earth, and it would have been fine by me if we were.

Warning Signs

You can only know if you truly loved someone with time and reflection, and even though I know I was in love, the reflection is painful, because hindsight brings clarity to the problems I ignored. Before she came to live with me in the summer of 2013, Lucy took a spring break trip with her friend Mena. It was their third year of law school and their itinerary included Thailand, Dubai, and the United Arab Emirates. I knew I’d be transitioning between training in Newport and my first duty station in Tampa, so I told her to go and have fun. She never even feigned the hope she could stop in Tampa to visit or that she might like to see me, and I didn’t get the full recap of the trip until she graduated law school and moved out to Tampa to study for the bar. We were sitting on my bed in the middle of the afternoon scrolling through the photo album of the trip on her MacBook.

She suddenly stopped scrolling and there was an awkward pause, before she continued and tried to casually explain how some guys in Dubai invited her and Mena on their boat. She looked back to the computer and kept scrolling.


There she was in a skimpy pink bikini top and tiny teal bottoms, her beautiful tits overflowing while she sat in the driver’s seat of a large yacht. She was smiling, holding a drink, red faced with glossy eyes.


There she was on the bow of the yacht with her head thrown back, basking in the sun.


There she was down in the water, splashing around with a group of swimmers, waving and smiling for the camera.


There she was on the bow again, in her barely-there string-bikini, with her head thrown back in a laugh, drinking, with a flirtatious smirk on her face.


And there she was sunbathing on the bow of the boat, laying on her flat stomach while a fat, hairy, dark-haired bastard laid perpendicular to her, resting his head on the small of her back but lifting his stupid fucking face just enough to smile for the camera. They looked like a really happy couple enjoying their vacation together.

I got sick to my stomach. It was all so cliché, and something vile bubbled up inside me. My girlfriend: The 25-year-old American abroad in a skimpy swimsuit with her buoyant tits, wooed over by the allure of a fancy yacht, the clear blue waters of the bay, and the moon-scraping glass buildings in the background, flirting with and cuddling up to four fat, hairy fuckers that probably never worked a day in their lives. I hated her for those pictures, I hated the men on the boat, I hated their luxury, I hated the excess, I hated the trip they went on, and I hated Mena.

Don’t be jealous, I told myself.

Don’t get angry, I encouraged myself.

She didn’t have sex with them, I begged myself.

It didn’t help that Lucy had previously described Mena as someone who was ‘not that into her boyfriend,’ and yet while I wanted to scream at her, jealousy and insecurity are not attractive character traits, so I was appeasing and tried to act like it was no big deal. She could tell it was a big deal though, and in a passive-aggressive way we let the moment pass. But who was I to judge? Two months earlier I was in Austin, Texas, with a beautiful naked woman asking me if I had a condom. All she’d done was go on a boat with some rich dudes. I knew I was in the wrong and felt guilty, and yet I felt like her behavior retrospectively justified my near-transgression.

I had visions of Lucy engaged in group sex with those three fat, hairy Arab bastards in a penthouse suite overlooking the desert wasteland of the UAE. I pictured one of them pounding away at Lucy while Mena was double-penetrated by the other two, and it wasn’t just mistrust I felt – it was a burning, toxic jealousy. I didn’t have a fancy yacht or nice things. I took Lucy on modest vacations, bought her ordinary gifts, and couldn’t afford that much. I wanted to buy her whatever she wanted, to travel with her, to wow her with luxury and excess, to give her everything and anything her heart desired.

Then jealousy was replaced by blind rage and delusional fantasy. Lucy was so smart, so morally upright, and seemed to be above such banal luxuries as giant yachts and glitzy accessories. But if she could be persuaded to loosen her morals by a shiny watch and a big boat, I imagined anyone could. I fantasized about luring young, hot European vacationers to my imaginary yacht. I fantasized about taking them back to my large penthouse for a wild orgy. I know if Lucy had really cheated, she wouldn’t have shown me the pictures at all, but they were seared into my brain. The nightmarish fantasies continued, and it was just another poisonous layer added to whatever distrust we both already harbored after our career paths drove us inexorably apart.

There were other warning signs that felt like a million tiny fissures, like how she seemed to always choose something or someone else over me. She would do this in small, justifiable ways that were frustratingly hard to question, like when I’d invite her to Florida while she was in Guam. She explain that she’d like to visit me, but that the whole purpose of moving to Guam was to travel and see the world.

Can’t argue with that, I thought.

Or how I spent a dozen holidays with her family in Long Island, and how she visited my family in Redding exactly once. But had I invited her enough? I didn’t really like spending time with my family after all.

Or how I wanted to Skype constantly while she was away, but she seemed indifferent, like our relationship was an afterthought to her. Was that all in my head?

She always said the right words, like how she was busy with work or that the timing was off or that she cared about me, that she loved me – but she didn’t have a very good way of showing it. Sometimes I wonder if these were actually warning signs, or if it was my fault and I just made them all up.

Relationship Status Bullshit

The constant shifting of relationship statuses while Lucy was in Guam and I was in Florida was exhausting. Either you want to be with someone or you don’t, and we were lying to ourselves.

Right away it didn’t work. When we started off in an open relationship and I’d meet other girls, I’d compare them to Lucy, and then I’d be disappointed when they weren’t everything that Lucy was. Or I’d go weeks without getting a date or finding matches, grow frustrated, swear off the swipe-apps, and then get lonely for Lucy, who I knew was half a world away. So I’d vow to meet someone in person, go out for a night of heavy drinking, spend hundreds on getting disgustingly wasted, drunkenly shout sentence fragments at unsuspecting groups of pretty girls, close down the bar, stumble home reeking of liquor, and then pass out fully clothed reeking of bitterness. No one is sadder than an intoxicated lonely man who starts the night with high hopes for meeting a pretty girl and ends it alone, and I was That Guy. I know I should have joined a Pilates class or taken up sailing, but instead I hoped for pity and/or dumb luck. Even when I was pounding Cindy’s pussy or getting my dick sucked by Amanda the Christmas Tree, I was emotionally hollow. With Lucy, I had love. Now I had nothing.

I started counting down the days until I could see her again. The first chance was at Christmas, when she would be flying home from Guam to Long Island. I flew up to spend the holiday with her, but it was barely a blip on the radar of that torturous year because it went by so fast. The physical distance had translated into an emotional distance, and it felt like the early stages of getting to know each other, not a couple in love who’d been dating for two years. I drummed up all the insecurities of when we first met, and it was just like that holiday I heard over the phone – the dogs barking, the hustle and bustle of a busy house, and the New York-ness of everything. We had precious little time alone.

When she dropped me off at the airport, I felt the tension of not knowing it was going to work and I could feel her slipping away.


I visited her in March of 2014, and the flight to Guam felt like a trip to the moon – almost 20 hours of travel. I stepped off the plane and walked through the deserted airport to the baggage claim. The beads of sweat on my skin were possibly the result of nerves, food poisoning, or just the suffocating humidity, but I was so excited to see her I just wiped my brow and smiled in anticipation. In the days and weeks leading up to this trip, she’d seemed excited by my visit and we still flirted and joked with each other while video chatting, so I thought that this could be a fresh start.

After collecting my bag, I stepped out curbside and there was Lucy pulling up in her shitty white two-door sedan that I’d seen in her online pictures. Guam is a tropical time warp, like being transported to Hawaii circa 1950, and the dilapidated airport and the drab, volcanic nature of the island depressed me. Then she parked her car and got out, and when I saw her, dressed in heels and with makeup on, my repressed resentment, unspoken animosity, and nervous doubts washed away. We embraced and everything felt right with the world. She curled up in my arms and I kissed her forehead.

“Hello,” I said.

“Hello,” she smiled up at me.

It felt like home, and I was happy.

That feeling lasted about two minutes. As she gave me the window tour of the godforsaken prisoner’s island she chose to inhabit for that year, she casually mentioned that she couldn’t get much time off while I was visiting.

Huh? What do you mean?

She said work was super busy. She had a trial coming up and needed to prepare bench memos. I’d taken two weeks off and flown for 20 hours. I suppose I could have told her to turn the car around, got back on another 20-hour flight home, ordered 15 of those tiny little bottles of vodka, flirted with the flight crew, and forced the pilots to land in Miami out of fear I was going to set my pants on fire, but I was on a tropical island and I was going to have a good time, goddamnit – with or without her.

I did, and while she didn’t take that many days off, for the next two weeks we hiked, went scuba diving, snorkeled, and cruised around the island together. We went to dinners and hung out on the beach. We did happy hour with her co-workers at the fancy hotels. We tried to stay cool, despite the punishing humidity. We pretended everything was normal and got along in the same familiar, congenial way we always did. We pretended everything was normal, even though it wasn’t.

No Coming Back

Right when I got back to Tampa, the Navy told me I’d be leaving the following year and started the discussion of where I’d be going next. Lucy always talked of wanting to be on the East Coast, close to her family, and I had no complaints so long as I was with her, so I told her I would work every angle to get to Washington, D.C., and started negotiating with my bosses to make it happen. She decided to take the New York bar exam, and things were looking good. She’d easily get a job in New York or D.C. – either way we’d be close and we’d make it work.

Just get through the year, I told myself.

Then things really went downhill. First, she voluntarily pushed her return home from early August to late September. As I was counting down the days until I got to see her again, she just added an unexpected 60 to the total. Then something else happened, which requires some explaining, and which will probably telegraph exactly where this is heading. While she was in Guam, I had been borrowing an old iPhone of hers. When I left Guam, I unwittingly left it behind. Rather than dealing with the hassle of having her send it, I bought a new phone and she took the old one back and shoved it in a drawer. Then, the phone she used in Guam broke so she turned on her old iPhone. At this point it was July, and there was light at the end of the tunnel – I thought we’d both be in Washington, D.C. or New York soon, and after a trial run of living together I had visions of taking things to the next level. Then this arrived in my inbox:

From: Lucy 7/14/14

To: Me


I was looking at my iPhone to see if the screen was good enough that I could use it next year as a cellphone. I saw a bunch of iMessages to numbers from all over the place. They were from last May (2013). To be clear: I would never read your messages or go through your stuff but once I accidentally saw one, I had to look through them all.

In case you don’t remember, you were talking to a bunch of girls who it sounds like you might of hooked up with or they were across the country or I don’t know what you were doing (slash have been doing all along?) but it was definitely flirty and there were pictures and it was pretty gross actually. If this was from now I probably wouldn’t want to know and I know I couldn’t get mad, but at that time I was about to move in with you in Florida and we were very much together, so this is a problem.

I honestly don’t know how I feel about this. It IS weird though because you really had me convinced that you were not interested in other people. I realize that I don’t know what this is all about, and maybe there is a benign explanation, but it is pretty shady. Although I’d like to hear an explanation, I don’t think we should get into it right now. The bar is in less than 2 weeks and I am overwhelmed, so I think that it might be best if we just don’t talk until after the bar. I’m not saying this to punish you or be passive aggressive. I just can’t deal with any kind of emotional breakdown or stress right now. The bar is too soon and I am just going to push this out of my head until then. But I don’t want to have to pretend to you that I never saw all this. Anyway, email me or message me if you want, but I’m trying not to have a really dramatic talk this close to the bar exam.


Two days later she sent this:

From: Lucy 7/16/2014

To: Me

OK now that I have had time to reflect on this and am no longer in shock, I’d like to retract my previous statement and let you know that I am furious and heart broken and feel like total shit.

Ouch. You can’t really come back from that.

July 16, 2014 was the worst day of my life, because that was the moment I truly lost her, and explanations and apologies just meant I had to relive my mistakes. At that time I was a prolific user of the swipe-apps but I only used them to boost my fragile ego. That first one-night stand with Cindy and the sex rampage that followed was still six months away, so the transgressions that she perceived were – in my mind – just innocuous flirting. She was right though – the timing was bad, and the flirting wasn’t so harmless, because she was hurt. And on that fateful day, when I read those emails of how upset she was, I wanted to crawl into a hole and die.

I apologized and agreed with her endlessly with fawning sincerity. I wanted her to know that I only flirted with those girls because I was hurt, and I only did it after she decided to move 8227 miles away to a remote island in the North Pacific Ocean. I know that’s no consolation, and I don’t think she ever believed me, but I had to tell her the truth. If love makes you crazy, the prospect of losing your love makes you panic, and I was panicked.

I asked that we talk in person (or at least over the phone), because if there was a magic formula to digging myself out of this hole, I was going to figure out what it was. She told me she needed time, so of course I did the opposite and suffocated her. I would email and text constantly. I would send flowers unprompted. I would sit at my desk in Tampa and look at flights to Guam, getting all the way to the payment screen, and then realize how badly flying to Guam on a whim could backfire, and what a stupid, desperate act it was.

Then things got worse. Lucy emailed me to tell me that she wasn’t moving to New York or D.C. – instead, she accepted another judicial clerkship, this time in San Francisco. Was she intentionally trying to ruin my life? Or had I ruined my own? I had negotiated orders to Washington, D.C. and would be there in the summer of 2015, and it seemed a cruel twist that she accepted a job in my home state, where, if given the choice, I would have much preferred to be. Was she just fucking with me? Was this just more punishment? Maybe it was simply karma. When she told me the news that really should have been goodbye, but I’d lost track of the person I was before I met Lucy (thank God), and I felt empty without her. I was desperate, so instead of wishing her the best and telling her I was sorry one last time, I offered to help her move.

And she accepted.

Losing Lucy Forever

My friend Seamus warned me. He told me it was time to give up. First Guam, and now San Francisco. She was deliberately choosing locations as far away from me as she could get. But she was still talking to me, I argued. “Well, you’re talking to her,” he said, “and she’s answering you. It’s not the same thing.” We’re working things out, I insistently told him. “How’s that going?” he asked.

Of course he was right, but I was beyond reasoning with.

In September of 2014 I flew to San Francisco. I was going to do anything to win her back, even if it meant standing outside her window holding a boombox above my head blasting In Your Eyes by Peter Gabriel. To make matters worse, she’d agreed to let me book two tickets – first, to move her into her new place in San Francisco, and then to visit her again for Thanksgiving. I was accepting any olive branch she was willing to extend, and I was going all in.

I lugged her suitcases all over the city. I moved her furniture. I bought her dinner. I bought her flowers. I apologized profusely, and clung to whatever tattered shred of companionship we had left. It was not reciprocated. I remember one day when we visited the Rose Garden in Golden Gate Park. I eyed her curiously from a distance as we drifted through the grassy maze of flowers, and I tried to figure out how we’d become such complete strangers. I watched her, wondering skeptically if I had any hope left, or how long it would take to earn her trust back, or, worse, if she’d finally say the only words to get me to stop trying: “It’s over.”

During intimate moments in the evening, she’d just look at me with a blank stare, like she had no idea who I was, and the moments alone in our small, one-bedroom Airbnb were uncomfortable in a familiar way. When we said goodbye, I walked out the door of her apartment with the hope that Thanksgiving would go better. I’ll be back in a few weeks, I thought. I boarded the metro and sat on the cold, hard plastic seat, staring at my shoes and thinking about all the things I’d done wrong. Then my phone rang.


“What are you doing?”

“I’m on the train.”

“I can’t do this anymore.”

“What do you mean?”

I was going to make her say the words. I’d just flown across the country, so if this was truly going to be the end, she was going to need to say the motherfucking words.

“I don’t want to be in this relationship anymore.”

Never had I heard more certainty in her voice.

“I think you should cancel your plane ticket for Thanksgiving,” she continued.

Fuck. You. Is what I wanted to say. Instead, I started crying.

“Okay,” I said, sobbing. “I understand, and I’m sorry. I’m sorry for everything.”

I sobbed into the phone and I told her I understood her decision and that I hoped she’d change her mind. I groveled, like the pathetic shadow of a person I’d become, and then hung up. When I looked up, I realized everyone on the crowded subway was staring me, a grown man choking back tears, with snot dripping down my face. I didn’t give a shit. I just lost the love of my life, and if I wanted to have a really good cry on the subway, I was going to.

Part Two: Is Love Possible on the Swipe-apps?

Here for the Right Reasons

My friend’s sister just got married to a man she met on Tinder, many of my close friends met their mates on the swipe-apps, and it seems like every other couple I’m introduced to is dating because they both swiped right. The swipe-apps have moved beyond being used for just hooking up, and regardless of how you meet your significant other – whether you ran them over with your car or you met them on Death Row – if things click and you become a couple, you’re not going to care. Love is love, no matter how you find it. But the swipe-apps have made online dating harder, because in the world of attention deficit disorder-inflicted millennials and the ease with which one can trade up to a ‘better’ partner, there’s less and less people interested in settling down. People don’t want someone who’s ‘good enough,’ they want someone who’s perfect.

Take my story:

When I turned to the swipe-apps, it was because I was on a self-destructive mission to find as much strange ass as I could my hand on, or in. I was looking for debauchery, not lifelong companionship. I had completely forgotten (or at least disregarded) the usual characteristics important in building a meaningful relationship, such as patience, understanding, and empathy. All those went out the window when I first downloaded Tinder, and they persisted when I used Hinge, Bumble, and all the others.

Remember Floral Print Sports Bra? She lasted three dates because she was not down to fuck. Brianna the Ballet Dancer lasted slightly longer, but that’s only because she had a charming personality and fantastic tits. They were both cool, good looking, smart, and fun girls to hang out with, but because I was going through a period in my life when I was a total piece of shit, I had no interest in finding love. Men are notoriously promiscuous, and the swipe-apps make it so very easy to be that way.

Once I cracked the code of attaining Zach/Jason Sudeikis-level confidence, the formula for getting pussy was shockingly easy:

1) Meet my date for a drink or dinner.

2) Engage in playful but mostly superficial conversation, and if things go well attempt to break the all-important touch barrier.

3) Walk date to car and kiss her.

4) Meet up for date number two.

5) Fuck like rabbits.

6) Repeat for as long I could before I was confronted about commitment or until I found someone better.

Eventually, the woman I was doing this with would ask the probing questions they should have asked in the very beginning, like,

“Are we dating?” or,

“How come we never hang out with your friends?” or,

“Why do you only come over here late at night and immediately try to take my clothes off?”

I’d tell the swivel-eyed interrogator I wasn’t sure I wanted to be in a relationship, which is code for, “I have no interest in a relationship whatsoever and want to fuck as many women as possible because I’ve lost my faith in humanity.” But saying ‘I’m not sure’ or ‘I need time’ is a lot gentler and avoids them setting you or your car or your apartment on fire.

For the women who’ve made it this far in the book without throwing it away, burning it, sending me death threats, or doing all of the above, I have some advice. If you’re looking for more than just a hard dick to ride, I don’t want you to fall victim to the perilous circumstance of having your time wasted by a douchebag like me. You need to quickly dispose of the guys who are clearly just trying to get in your pants, even though that could turn out to be all of them.

Here’s a few obvious tips that you might need to be reminded of:

1) Don’t have sex right away. This age-old tried-and-trusted formula works because if he’s serious and actually likes you he’ll happily wait a couple of weeks. If you’re hot enough, cool enough, or a combination of both, he’ll determine you’re worth it, and he’ll wait. If you’re not that hot and/or not that cool, you definitely want to wait, because he will quickly stop calling you back, and you’ll have the certainty of knowing his motivations. Perhaps the only exception to this rule is if you have a magical vagina that will make him fall in love with you, but be careful of overconfidence because every woman thinks their pussy is the greatest pussy on Earth. Hopefully this isn’t a surprise, but it’s important that you understand it’s not true – yours is not the greatest pussy on Earth. And, even if you do have a magical vagina, you may just be delaying the inevitable. Remember Brandy Brunette? Her vagina was the Rolls-Royce of vaginas, and the allure of fantastic sex just meant that I endured more conversations about her favorite Disney characters or how we should raise our kids than I would have otherwise tolerated. Eventually, I was going to split or find the tallest building in Tampa and jump off it. So by not vetting me, she allowed me to manipulate her and ultimately waste her time. (Don’t worry, I hate myself too.)

A man will stick his dick in a warm apple pie if he thinks it will get him off and no one’s watching, so by waiting to have sex you can avoid him thinking of you as a warm apple pie. Make him appreciate you as a person by making him wait (but not forever, or he’ll get bored).

2) Ask him if he’s cool with commitment. This one is tricky and fraught with peril, because you have to ask him without actually asking him, or else he’ll run for the hills. Be as gentle as a therapist trying to pry out a story of child sex abuse, because there’s no greater turnoff to a man than a woman who puts unwanted pressure on him. If he thinks for a second that you want to have his babies, he’ll get the hell out of there (unless of course he actually wants to have your babies, which means you’re a supermodel and/or a rocket scientist, which means you’re probably not actually reading this book but accidentally opened to this page while at a friend’s house, and if that’s the case you can fuck off because you were dealt the Royal Flush of genetic poker hands in the first place).

I realize that is maddening and absurd to say you need to ‘have the conversation without actually having it’ and in an obtuse way, but it’s a way better strategy than writing ‘N0t here 4 a ho0k up’ on your stupid fucking profile, since every man on the planet will either ignore that statement or swipe left. If anything, by writing that on your profile, you’ve tricked yourself into thinking your matches are into commitment. I had plenty of matches who wrote ‘N0t here 4 a ho0k up’ on their profile who by the third date were screaming in ecstasy as I drilled my cock into them.

Bottom line: Ask him if he’s into commitment, but do it in the vague, contradictory, confusing, magical way that women communicate.

3) Age matters. The older the man is, the more likely he is to commit. Every 22-year-old man thinks his life will be a never-ending parade of gorgeous women in their early twenties wanting him to blow his seed on and in them. Blame it on online pornography or egotism running riot or whatever. He thinks this because he just finished college, he’s working in some retail or service-industry job where he’s interacting with young attractive people all day, or because the media has brainwashed him into thinking everyone can be Leonardo DiCaprio or George Clooney crossed with Ron Jeremy. Right now, he’s probably having sex with gorgeous women on a regular basis, and he thinks this phase of his life will last forever. For men, delusion and stupidity are at its peak at the age of 22.

Like everything in life, there are exceptions to these rules, and not every ‘older’ man is looking for commitment. I was a 30-year-old man with the emotional maturity of a 15-year-old who never once considered commitment, and that’s why the above vetting process is so important, and age is just one of many factors. Of course there’s a lot of other considerations, but those three tips are a good place to start if you’re female and considering the swipe-apps.

A Self-inflicted Double Standard

The same need for men to vet women for their level commitment is not necessary. I have been on just about every swipe-app you can imagine, and I have yet to see a profile from a female that says something even remotely close to: ‘Not interested in anything long term. Down for something very carnal yet casual,’ whereas that is implicit in pretty much 90 percent of men’s profiles.

No woman who is really hot, really cool, or both, is available and looking for casual sex.

Here’s a Venn diagram of how the dating pool starts to seem after a while, at least from a man’s perspective:

Which is fine, because if you’re a woman looking for a serious relationship, you can forget about the casual sex – it’s in your best interest to.

Lastly, for men: Be advised that the ‘insane’ category might look passingly attractive to you. Caveat emptor, because the risks of getting involved with that lot include threats of pregnancy, being punched in the face while you’re balls deep in her, returning back to her place to find your clothes have been thrown in a dumpster, or her dog likes to watch you fuck and she’s cool with that. It doesn’t matter what age the woman is, even if she tells you that she’s only interested in something casual, she’s probably lying. If a woman fucks a man and doesn’t call him back it’s not because she doesn’t want commitment, it’s because she doesn’t like him that much.

Is This for Me?

By the time the Navy moved me from Florida to Oceanside, California, I was running on the fumes and vapors of self-destruction and over-confidence that I had in the tank, but I was slowly losing interest in nailing every single chick I swiped right on. At first, sex with strangers was the only thing that took my mind off the feeling that I was going to be alone forever, but the adrenaline rush wore off with each successive conquest, and after enough confused early mornings with hungover virtual strangers, their crying fits after I failed to commit, pregnancy scares from total psychos, and feelings of despair when I’d find myself alone late on a Friday night, I realized that none of my relationships meant anything more to me than just fucking. Shocker, I know. The only feelings that were recognizable to me were self-loathing and pity (both self-pity, and pity for whoever I had to watch bawl their eyes out when I told them I didn’t want commitment). I figured I was destined to die alone.

Once I realized with Lucy that you can’t make someone love you back and accepted that she was gone forever, the easier it was for me to commit emotionally to someone new, but the women of Florida never really had a chance. Sky, with her broken, smashed up pussy and her sassy attitude, was wild and unpredictable in a slightly frightening way, but it also made her exciting. Her experience in bed made her a fantastic fuck buddy, but I didn’t want my future wife to be a former service-industry employee hipster who’d been ridden hard and hung up wet. I knew too much about her that I didn’t like – the drugs she did and the men she fucked. So while it was nice to imagine my future wife being willing to drop to her knees in the middle our kitchen and suck me off merely because the mood struck her, and while it might have satisfied some deranged hedonistic/misogynistic urge to blow my wad all over her face, I also couldn’t help thinking she’d be kissing our kids with that mouth. She seemed too much for a prude square like me.

Brandy Brunette was closer to my speed. She’d only slept with five people, she had a picture-perfect pussy, and she was a sweet, kind, gentle person. But her personality was grating on the nerves, she was whiny, lacked ambition, and there was almost nothing interesting about her other than the aforementioned pussy. She was the opposite of Sky in every way, and there was no intrigue. Plus, she was a self-professed born again Christian who wanted to write inspirational books for young girls about the power of abstinence, yet there she was, riding my cock in the driver’s seat of my car on our third date. She was a slutty hypocrite. I wasn’t complaining at the time, and there’s absolutely nothing wrong with a woman that fucks on the first, second, or third (but no more than that) date, but as well as betrayal, there’s little else that bothers me more than hypocrisy. I like people who live their values. If Brandy and I married, we’d have been divorced within a year.

Cindy, Amanda, and Leslie: One had the body of a 16-year-old boy, one was too ‘meh’ and liked to dress up as a Christmas tree, and the last was a former child bride with so much baggage that decades of psychiatry would barely make a dent. I started to think maybe I was just being way too picky. I’d met dozens of girls in my year-long sex rampage, and none of them came close to girlfriend material, so I thought the swipe-apps might be the problem and I deleted them all. I didn’t exactly know how much my inability to find a monogamous relationship in Florida was attributable to my attitude and how much of it was the poor quality of females on the swipe-apps, but either way I was depressed. Despite scoring with so many women so frequently that I was becoming sleep-deprived, I felt more and more hopeless, and decided I wanted to meet someone organically – just like how I met Lucy.

That lasted about two months. Like a heroin addict with an unshakeable attraction to hypodermics, no matter how many times I told myself I was done with the swipe-apps for good, I always came back. I reverted to the scared child with the paralyzing lack of courage because that promising encounter with the cute coffee shop barista or the beauty in the grocery store checkout line would inevitably end with learning that they were one half of a happy couple. I’d find out they had a boyfriend or husband waiting at home, and they were just being nice, friendly. The swipe-apps eliminate that guesswork, because if you’re on the swipe-apps, you’re by definition looking for someone, or something.

My compromise was the decision to be open-minded but transparent. Fun, but not manipulative. Eager and willing, but always truthful. No more having to wipe away tears, gather my things, and then leave in disgrace. No more evasive statements about whether or not I was seeing other people. I wanted to find love on the swipe-apps, and I held out hope that it was possible.


Sometimes, the person you match with on the swipe-apps turns out to be everything you ever wanted in a partner, you’re just missing that wildly lustful attraction that should ideally fuel the fire of your relationship. That was Lily. She just wasn’t that physically attractive.

Lily’s photos were touristy – her at music festivals, drinking with friends, at an amusement park, and a pic of her in front of the Hollywood sign. When we met up for a drink at a fancy bar in Orange County, I realized she was in fact a tourist (kind of). As she explained in her cute Scottish accent, she had a work visa as an au pair, taking care of the daughter of a power couple who were both pharmaceutical executives. She was five foot six with sandy brown hair, beautiful green eyes, a flat oval face and a broad but thin-lipped smile that made her look like a bug. She was an attractive bug, but average in every way – boobs, legs, and a paunch of flab surrounding her belly that was evidence she’d never run more than a couple hundred yards in her entire life.

Like everyone on the swipe-apps, she was much prettier in her pictures, but she’d say funny things like ‘jumper’ instead of sweater, ‘bollocks’ instead of bullshit, and she threw in bitter witticisms into every day conversation befitting of someone from across the pond. At 25, she was a few years younger than I was, but she was smart, sweet, charming, and worldly. (Or maybe she just seemed smart because everyone in America is an idiot, but either way she was pretty funny and a great conversationalist.) We had an incredible time hanging out, but I wanted to feel that lustful urge to sleep with her every time she walked in a room, and while the sex was just fine, it always seemed much better after I’d had a couple drinks. Referring back to the Venn diagram: She was very cool and interested in casual sex, but not that hot. So to remedy this I drank. Heavily.

Fortunately, her au pair duties were ending soon, so when they did saying goodbye was much less complicated. We said goodbye, she went back to Haggistan, and we kept in touch. And if you think I’m shallow for not wanting to pursue things further, the next time you’re at your local watering hole, pick out the ugliest person who nevertheless has a great personality and go fuck them. I remember once I was on wingman duty while on vacation with friends, and a very blunt woman who was also funny, charming, and a great conversationalist, asked me, “What can I do to get you to like me?” The answer, if any woman is reading this and wondering, is simple: ‘Be more attractive. And don’t dress like a Christmas tree.’ I don’t like the rules any more than you do, but I also didn’t make them up so don’t fucking blame me. Lily may not have been the love of my life, but just enjoying her company made me feel slightly better.


Cherish was the opposite of Lily, because she was straight-up drop-dead gorgeous. A 25-year-old vice president of an Orange County bank, she was a dark haired beauty with big, expressive eyes, a smoking-hot body, and delicious little B-cup tits. Every time she walked into the room I lusted after her. The problem is she was insufferable.

We matched on Bumble, and she was that rare catch where she was even prettier in person. Her stripper name was incredibly misleading, because she was a classy, refined, yoga-pant wearing, stuck-up elitist bitch with a rotten personality who was also totally insane. She was a Jewish-American Princess snob who only cared about money, but she was successful, and the kind of gorgeous girl with steadfast determination to maintain her attractiveness and keep her body highly refined and maintained. It wasn’t like putting lipstick on a pig, because she was good looking already, but enough money can easily take a woman from a ‘6’ to a ‘8.5.’

I liked all of that, but she wouldn’t shut up about how she worked on The Hill after college, or who owned what house on which beach, or how much money she made, or how much others made, and how she wanted more. Talking to her was both boring and exhausting, and her status on the Orange County socio-economic ladder seemed to be the most important thing in her whole life. Luckily to offset this the sex was amazing, so just like Brandy Brunette it kept me around much longer than I would have otherwise stayed, but I would’ve rather have my toenails ripped out one by one than have another conversation about how much some fancy beach house was worth.

Cherish was proof that the moments between sex are infinitely more important than the sex itself, and our routine of me driving the 45 minute commute to Newport Beach a couple times each week so we could fuck like rabbits quickly wore out. Inevitably she confronted me one night and asked why we never hung out on weekends or did dull boyfriend-girlfriend things. I told her I wasn’t really looking for a relationship, she bawled her eyes out, told me to leave, and I never spoke to her again. Oh well.

There was Megan the (other) crazy doctor, Hannah the MMA fighter, Emily the bartender, and Mena the law student. Nobody stuck, and I started to think: Forget love, I just want someone I’m attracted to and could put up with without wanting to kill her or myself.

Compromising seemed like the worst thing to do, because that seemed to be the primary driver for divorce. I didn’t want to sacrifice some big, important category that I wanted in my partner just for the sake of not being alone. It seemed like I would find someone I was wildly attracted to but couldn’t bear to be around (Cherish) or someone who I loved hanging out with but had to get a little drunk to have sex with (Lily).


Then I met Courtney. Courtney was cool, easy going, friendly, warm, upbeat, into fitness, had a gorgeous body, giant fake double-D tits, was incredible in bed, and had a vagina in a good state of repair despite her extensive ‘experience.’ She gave great head, loved sweaty, nasty sex (and didn’t seem to mind having it with me), was great in bed, and was also kind and sweet. But again, something was missing, and I realized that the moments between working out or having sex were strained and difficult. Then I realized what was wrong – we were just not on the same page mentally. I didn’t need her to be a rocket scientist, but she was Dane Cook to my Demetri Martin. We couldn’t talk about politics, books, art, or even sports. We both liked working out and we enjoyed sex with each other, but that seemed to be where our interests started and ended. She was hot, nice, and perfectly agreeable in every way, but I just couldn’t fake it. There was nothing dynamic about her. Her personality was one-dimensional. I decided she couldn’t lie to her and I couldn’t lie to myself, so I called it off.

The panic over being too picky and judgmental set in again, and visions of being a grumpy old perverted bachelor attending junior college football games just so I could stare at the cheerleaders’ tits bounce up and down haunted me. If I couldn’t appreciate a sweet, funny, fitness fanatic with a porn-star body who was fantastic in the sack, how was I ever going to find anyone? Courtney was so great, but something just seemed… off.

Was God punishing me for my last two years of selfish hedonistic abandon? Was I really going to be alone forever? I know now it was the former, because that’s when I met the fantastic fuck-doll Alyssa, who turned out to be much more conniving, manipulative, and devious than just a casual lay. She bent my weak will until I started to believe she was something more than a nutty vessel meant to fulfill my every sexual desire. She manipulated, connived, and fucked her way into the depths of my mind until I was so hypnotized I thought I might be in love.

Saying the Words – Alyssa

While the name ‘Oceanside’ might imply a blissful paradise by the sea, it’s actually a crime-ridden hellhole in the middle of nowhere with absolutely nothing to do if you don’t dig piers. A good 45 minutes from anything worthwhile, Oceanside’s demographic consists of gang bangers, burnt-out drug-addicted surfers, military retirees, migrant farm workers, and people who dug piers. If you’re between the ages of 25 and 35 and looking to date, you might as well be living in Siberia. Oceanside is a social wasteland, and my options on the swipe-apps dried up pretty fucking quickly. But I was only an hour away from San Diego, where many of my college friends still lived, and there were so many options on the swipe-apps that during every visit my phone would start buzzing like a 1980s drug dealer’s pager.

That was how I found the gorgeous doctor from Houston who was fit only for a straitjacket. And why, might you ask, does she re-appear in a chapter titled ‘Love’? That’s because, a year after I’d broken up with Lucy, as embarrassing as it is to admit out loud, Alyssa was the next person I said those three magic words too. She might fall comfortably in the ‘insane’ category of the Venn diagram, but maybe I’m a little fucked in the head too. Despite having the emaciated face and stringy hair of a middle-aged meth addict, she could be sassy and sweet at times, she had a cute dog, and she seemed curious about the world. She may have embarrassed me in front of my friends, caused a scene on our second date, and punched me hard in the face during sex, but she was still a five foot nine, blond-haired, big-titted successful urologist who stood to make hundreds of thousands of dollars for the rest of her working life. She was so good on paper, and it was hard to leave. Plus, her mom committed suicide when Alyssa was only 20, her dad was a twisted alcoholic, and she had dependency issues and fear of abandonment. She was so sympathetic in so many ways, it seemed forgivable that she was a wacko. I’d developed a savior complex, and I wanted to save her from herself.

Which was not easy, since every other conversation I had with her included some damning admission or terrifying anecdote. The conversations would start with some small flippant statement by her, like the fact that she took Adderall ‘sometimes,’ and then morph into something increasingly disturbing, like how she actually swallowed them like candy by the handful, and how she first procured a sample from a medical school lecturer who wanted to sleep with her, and how she went on to frequently fuck him in exchange for his magic beans. Once she started her medical residency, she got a prescription for herself, but would take so far above and beyond the recommended dose that she resorted to buying it off-label as a street drug. She admitted taking as much as twice the prescribed dosage, and how she begged, borrowed, and stole it whenever she could to fund her habit. She’d take it late in the evening to work on papers, and always needed more than a couple beers at night so she could sleep. The peculiarities didn’t end with her substance abuse history. Her obsession with her little dog Stella was beyond healthy, and she required Stella be nearby when we had sex. After we’d both come, that little bird-brained dog would lick up the sweat and spilled cum from the sheets, and when I pointed out to Alyssa just how fucking weird that was, she just shrugged it off. She’d call the little furball closer and cuddle her tightly, while I would lie next to them and watch in disbelief, sometimes with a cynical smile on my face, imagining all the men who’d fucked her in that bed and bore witness to this bizarre post-coital ritual. The dog would look smugly back at me with my stringy cum caught up in its whiskers as its nutty owner fussed over it. Perhaps the dog had its own jealousy issues and didn’t like me being there, who knows.

A story about an ex metastasized into how he was abusive to her, how the police were involved at one point, and how he still texts her from time to time when he isn’t in jail for any number of hideous misdemeanors. Yet I stayed. How I went from that night on the sidewalk, to all these crazy stories, to telling this person I loved her, I don’t know, but I felt like she used to almost goad me into saying it. During sex she loved to talk dirty, and while gyrating back and forth on my dick, she’d ask,

“Do you love it?” Yes.

“Do you love that pussy?” Yes.

And then she’d slip in, “Do you love me?” What? Faster and faster with me deep inside her until she came. Then, two months after our first date, in the middle of a sport-fucking session as I was plunging my cock deep inside her in missionary style, and I looked deep into her eyes and the words just came tumbling out:

“I love you.”

Ugh, what a fucking retard. I immediately regretted it, but it’s a bell that can’t be un-rung, and the next two months felt like an eternity. She put me through a lifetime of grief, confusion, anxiety, stress, and titillation, and when I said those words to her while in the middle of sex, it felt like saying ‘I love you’ was just another bedroom curse word that made the sex more exciting. Even though I didn’t mean it, it did make the sex even better, but I wasn’t in love, I was just addicted to Alyssa and all her chaos.

More Crazy Shit

Alyssa was the kind of person who confused affection for love and attention for self-worth, and I was more than happy to provide her with both. After one spat, and during a break from each other, she immediately went out and had a romantic encounter with a not-quite-divorced senior surgeon who was married with three kids, violating the hospital residency program rules against junior residents hooking up with senior attendings. She didn’t give two hoots. We were the definition of co-dependency, and she’d text me at every hour of the day, needing to know I was there. She always needed to be held, and was as toxic and emotionally erratic as any person I’ve ever known. I ignored the stomach-churning anxiety she created, the jealousy she brewed, the fear she manifested, and I fell victim to the lust she inspired. Something going terribly wrong seemed inevitable, and the dangerous uncertainty of dealing with someone so volatile kept me wanting more. I was also scared about the consequences of leaving her – what she might do to me or herself. So I stayed.

She was obsessively superficial and perpetually broke, so I would pay for everything despite the fact that I was working on a government salary and that in less than two years she was going to be making $500,000 per year. Deep in debt and surviving on her meager resident salary, she wanted to live like she was already a millionaire. She couldn’t afford basic vehicle maintenance for her leased Mercedes C-class, she’d spend $60 a month to groom her dog, and her apartment was furnished with tens of thousands of dollars’ worth of furniture and deco, but still she tried to get me to pay for weekend getaways, her hair appointments, a manicure, even a new swimsuit. Dodging monetary bullets should have been the least of my concern. Instead, I would have been smart to be more apprehensive about medieval sexual diseases, unwanted pregnancy, and having to be permanently and inextricably bonded to someone who was this mentally unstable.

In the meantime, I endured a slew of emotional slights she inflicted on me. She called me a ‘two-pump chump’ and a ‘one-minute man.’ She pressured me into taking Viagra, and told me she would write the prescription. She purposely tried to make me feel small, and did a pretty good job at it. Then, just when I thought she couldn’t get any more vindictive and volatile, just as I was ready to leave her for good, she would shrivel up into the most pathetic, desperate person and bawl her eyes out to me, telling me she had nobody in her life, and that I couldn’t leave her. The heart-pounding emotional turmoil was always followed by desperate and frenetic fucking.

She continued to unintentionally malign herself with crazy stories of her past. She told me all about her most recent relationship with a military helicopter pilot named Doug who she’d shopped for engagement rings with, and how that ended when she abruptly moved out of the house they shared while he was on deployment because, as she put it, ‘he was mean.’ Who the hell knows what really happened? Alyssa was totally insane and capable of anything. She told me about an ex she met while working at Hooters in college, how he impregnated her, and how after the abortion they stayed together. There was a fireman who she let fuck her for months. Her sister, a moderately successful Internet-famous dietician, had very recently used a Sugar Daddy dating service (read: Escort service) and had a ten-year-old-daughter.

Some of this information gave me the same titillating rush as when I pestered Lucy about her love life, but with Alyssa the facts were damning, troubling admissions that she had more emotional baggage than could be accounted for. Lucy told me about innocuous college sex, and stories where she’d been cheated on, lied to, or made to feel a little less than wholesome. I felt so sorry for her Alyssa and the grim pictures she painted of her sexual wasteland, I didn’t realize I should be feeling sorry for myself, and how far I’d wandered from someone like Lucy.

One night during dinner the hospital called her, and when she got off the phone I said something about how it would be hard for her to find someone who understood how important her job was. I was trying to show understanding, that I could see why she needed to take those calls, and that I realized how important it was. Instead she saw red, accused me of implying that she was going to be alone forever, and created a scene. I paid the bill and we left, but she wouldn’t let it go. We walked home in a huff, not speaking to each other, but ten minutes later she was bent over the kitchen counter while I fucked her in the ass. We repeated this scene for months, each time her manipulating me back. Even Alyssa admitted and acknowledge how toxic we were together, but because she reveled in drama and dysfunction, she once remarked, “I like how we are.”

The end was inevitable (again); the only question was how and when it was going to crash and burn.

More missed birth control, more pregnancy scares, more fights, more drama, and more degrading sex – it went on and on and on. We had a fight one night at my place in Oceanside. After I shot my load inside her, she mentioned that she didn’t take her birth control. First she said she’d absolutely have an abortion, that she wouldn’t want it to affect her career. Then she said she wanted to have at least one child, and how maybe “it wouldn’t be so bad.”

What!? I thought. Nothing could be worse!

The discussion turned nasty, I told her I was done, and that it was best we not see each other anymore. Tears streamed down her face as she stomped around, picked up clothes, and flung them into a suitcase. She screamed. She cried. She apologized and said she wanted to make it work. She called me names, apologized again, and cursed at me while bawling her eyes out. With her car running and packed bags lying at her feet, she announced she was leaving forever. I said that’s fine, but she’d been drinking so I insisted she wait until the morning. After ten minutes of threats, slights, and bitter accusations that dug up the worst of the brief time we’d known each other, she agreed to stay. We went to bed and before we fell asleep, we had sex one more time. My life had turned into a bad reality TV show. I should really make a bad night-vision sex tape and smear it all over the Internet.

Two days passed and I was on my way home from work when she called. Having nothing to say and thinking things were finally over, I rejected it.

She called again.




Six more times she called before I finally picked up. She apologized, told me she was an alcoholic and addicted to Adderall, and asked me to help her. She admitted she was recently arrested for a DUI and she wanted my help to get sober. She apologized and told me she would change. I have the breaking strain of a wet Kit Kat and instantly caved, and once again was driving to San Diego each weekend in search of my fix. It was like a bad dream that I couldn’t wake up from, no matter how hard I tried.

Each time I attempted to break up with her she’d call relentlessly and send tragically desperate messages until I responded. She’d leave sobbing voicemails until I answered. When we’d finally speak and I’d convince her that we should really, properly, seriously stop seeing each other, she would always add, “…at least we can still be friends,” which to her meant we’d still fuck like dogs, I would still stay at her place on the weekends, and she would still ask me to pay for everything. I was smart enough to only let the words ‘I love you’ slip out once, but I was dumb enough to fall into this manipulative trap each and every time.

Getting Out Alive

One Friday evening two months later, we were at a swanky restaurant in South Park, San Diego. I took the day off work to come down the night before, and hung out in San Diego while she went to the hospital. She’d spent the day popping way too much Adderall in between surgeries and patient rounds, so despite having eaten barely anything, late into the evening she still wasn’t very hungry. It was almost ten by the time we were seated at the restaurant for some food, and the kitchen was closing. As we sat and chatted, I pointed out a tall, slender girl at the bar and mentioned to Alyssa that she might be a good candidate for a threesome, which in normal circumstances is a cruel, insensitive thing to do on a date, but Alyssa herself had suggested the notion many times before so it seemed perfectly normal. My mistake, because at first she pretended to not know who I was talking about, and then when I could see from her expression that she didn’t like my suggestion, I apologized, told her I was just kidding, and that she should just forget it.

Five minutes later I was tapping out a text on my phone when she angrily scolded me – she accused me of texting another girl and told me I shouldn’t be disrespectful, even if we were just in a ‘friends-with-benefits’ type arrangement. I showed her that I wasn’t talking to another girl, it was a couple of male lawyer friends on a group text. Chagrined, she just shrugged and said, “Oh.”

A few minutes later she was texting and I asked who it was, to which she nervously stuffed her phone in her bag and curtly said it was no one important. I asked to see her phone, and when she gave it to me it wasn’t more than a fraction of a second before she ripped it back out of my hand. It wasn’t the act that bothered me, I told her it was the hypocrisy. By her own standards (ha!) she was being disrespectful, and I’d had enough. I got the check while she was in the bathroom, told her to fuck off, and walked out the door, leaving her sitting at the restaurant alone and no doubt about to burst into tears. It was still early so I figured I’d meet up with other friends, get my things from her house in the morning, and never see her again (again). Less than five minutes into my Uber ride I got these texts:

Alyssa (11:00 PM): Are u okay?

Alyssa (11:01 PM): U made me feel insecure and bad about myself

U kept looking at that girl

Then was txting

I guess I wanted to feel important too

Alyssa (11:02 PM): I knew exactly which girl u were talking about bc u looked her up and down when she walked by.

She’s skinny

And I not..

It hurt my feelings

Alyssa (11:04 PM): I still have feelings for u

But that was so un called for.

Alyssa (11:23 PM): I’m putting all ur shit in the dumpster outside the 7 eleven

Alyssa (11:24 PM): That s the last time u are going to humilate me you barsterd.

Alyssa (11:49 PM): Ur shit is in the dumpster

W ur wallet and keys

Alyssa (11:50 PM): Go to hell u crazy fuck

How much of this was bluffing on her part and how much was true I wasn’t sure, but I figured if she’d really thrown my things in the dumpster I should go back. Sure enough, when I arrived back at her house just before midnight, in the dumpster behind her fancy Hillcrest rental apartment were all my clothes scattered among the banana peels, trash bags, fast food waste, and lottery tickets, with my empty suitcase dumped on top. She hadn’t just zipped up the suitcase and tossed it; she’d maniacally shook out the contents and hurled the empty suitcase in after them. I fished out my belongings, stuffed them back in the suitcase, and commenced a hostage negotiation for my backpack. It was still in her house.

Finally, after inexplicable and empty threats by her to call the police, I got the backpack and left to sleep in my car. The next morning the childishness continued:

Me (6:02 AM): You’re an idiot and a substance-abusing, unstable disastrous fuckup

Alyssa (6:03 AM): And your emotionally unstable

I can’t give her points for originality.

I asked myself again: What had become of my life?

I was better off alone, I realized, and finally I did what I should have done that first night when she dumped all her emotional baggage on me and had me fuck her in the ass soon after: I blocked her number. But before I could, she called me 13 successive times, before I finally, stupidly, answered.

She wanted to be friends she said. I told her not to contact me again, and said goodbye.

Finding Good Enough

Alyssa was insane, and having my shit thrown in a dumpster, getting punched in the face during sex, and being semi-cuckholded was probably getting off lightly. I’m glad I wasn’t killed or arrested or wrongfully tried and convicted for some manufactured offense. So while that story is painfully embarrassing to recount because of both my behavior and hers, I suppose I should count myself lucky. I’d like to hold out hope that I can find love, whether it’s through the swipe-apps or through a friend-of-a-friend setup. But part of me thinks that the sad, unromantic philosophy of love that says you ‘just need to find someone good enough and then settle’ is probably true. Maybe someone as cynical and jaded as myself has to look at it that way, otherwise I’ll never find someone. After Alyssa, it’s hard to believe that there’s anyone above the age of 25 who’s good-looking, somewhat solvent, not totally insane, and eligible.

Maybe I’m just a miserable bastard, and I’m the problem – not the dating pool. After all, I’m a man above the age of 30 who’s still single, and I’m looking for love online with a hot young thing five to ten years my junior. There might be a reason someone like Alyssa is looking for love online, but there’s a reason I am too. Finding love is different for everyone, and there’s nothing wrong with finding The One online if it happens to you, but after my experience with the swipe-apps I can’t say they inspire much confidence.

Chapter Six



Part One: Reconciliation

The End

Of course I was never in love with Alyssa, but I yearned so badly for what I’d lost with Lucy that I think I just wanted to believe I was, even though I knew it couldn’t be further from the truth. Lucy had left me sobbing on the subway on my way to the airport, and I wish I could tell you that I was able to move on like a normal, well-adjusted person. I wish I could tell you that, because I did the opposite. I became an obsessed, crazy maniac.

I arrived back in Florida and tried to think of anything but her. Thanksgiving came and went. I moped around the office, drank heavily, and tried to forget. We didn’t speak for three months. Finally, in December I couldn’t take it anymore. I was angry and I wanted answers, so I reached out. I might as well have cut letters out of magazines, glued them to printer paper, and mailed them in an unmarked envelope.

From: Me 12/9/14

7:32 PM EST

To: Lucy

I know this is kind of out of the blue since it’s been months since we had anything resembling a conversation, but it’s really hard for me to not know what is going on in your head.

I know you don’t want to be with me, but when you told me not to visit for Thanksgiving I wasn’t exactly sure if you didn’t want me contacting you at all or if you just didn’t want me to visit for Thanksgiving and to stop calling you on a consistent basis. I know you don’t want me to desperately continue to try to win you back. I get that. I also understand that you don’t want to be with me. That’s obvious. However, while maybe you think your intentions were clear when you said “I don’t want to keep doing this,” there’s a lot of different ways I could interpret that statement. It was a pretty emotional moment, and I have unanswered questions. I don’t know where you stand.

Do you want me in your life at all? Do you only want to take a break, and maybe we should re-evaluate things around April? Whatever you ask of me I will completely respect your decision, and I’ll do what you ask, but I’d like to know what you’re thinking. I don’t really feel like I got any closure.

Maybe it’s not healthy, but I’d like to be able to write you occasionally, or chat with you once a month and say hello, or text you now-and-then, or send you funny things, without suffocating you (as I know I do). In other words, even if you think that there’s no hope for us ever getting back together, at least for now it’s hard to fathom losing you completely, and I’d like to try to be your friend. I hope that this stuff is at least something you’ve thought about, and I hope you at least try to clear this up for me.

If you want to chat about this or if you just want to email me back, that’s fine. I really just had to get this off my chest because I’m still a little confused. I hope you have a great time in New York with your family. It’s funny, I’m actually not going to be too far away from you guys. I’m visiting my sister and her husband in Princeton, NJ, from the 25–28th. It should be good to hang out with them.

I hope you respond to this in some way when you get a chance. Take care.


Even though I knew the truth – that we were done – I refused to believe it, and my crazy, desperate plea for answers sparked a back-and-forth email exchange. I employed a scorched earth strategy of broken-hearted, panicked, desperate loser. Spoiler alert: It didn’t work. She placated me with faux-sympathy.


From: Lucy 12/11/14

8:43 PM EST

To: Me

I’m sorry I wasn’t more clear in my conversation with you. I realized that I think the reason everything is and was so confusing is because I tried to explain everything I think without even knowing what I think.

I would like to give you closure if that is what you need to move on because I really care about you and I want you to be happy. But I don’t think talking over the phone is going to be productive at all. It seems like it will just be very emotional and I’ll probably end up saying things that confuse you. So I think it’s best if we talk over email.

I have to be honest with you that I really can’t see us getting back together. That seems like the ultimate question you were asking. I don’t think it’s really productive to get into the details but I want you to know that our breaking up was not, at the end of the day, your fault or because you talked to those other girls.

I would love to be your friend because I care about you a lot and because you were my best friend, but I think that first we need to move on a little bit. I just don’t think that it’s a good idea to talk until more time has passed. At the same time if you really need to talk I will always be here for you.

I don’t really know what else to say. If you have specific questions I will try my best to answer them, but I’m afraid to say too much and either make you sad, or confuse you, or create some other problem.

I am so sorry for how much of a mess this became and for making you so sad. I realize that I am not blameless in this but I do hope that eventually we’ll be friends. I really hope you are well. If there is any way that I can make this less hard please tell me and I will try.


From: Me 12/11/14

8:44 PM EST

To: Lucy

I just want to know why. That’s all. I just want to know what I did wrong or why you don’t want to be with me so I don’t make the same mistakes in the future or so I understand where you’re coming from. That’s all I want.


From: Me 12/11/14

8:46 PM EST

To: Lucy

I know I just wrote you but I really want to address this to get it over with. It’s been over a year and a half of hurt for me.

I don’t think you understand that the details – why you don’t want to be with me and what exactly went wrong – are exactly what I’m asking you. That’s the only way I’m going to get any closure here.

From my perspective it feels like you made the decision that we shouldn’t be together when you chose to go to Guam. It’s like breaking up with me was always in your heart and you just weren’t totally sure/didn’t want to break the news to me. The last year and a half have been like a slow twisting of a knife in my side. I’m doing (and have been doing!) everything and anything I can to show you how sorry I am for things going so wrong and how much I want to try to make things work, and I can’t even get you to tell me how you feel or why you don’t think we should be together or what exactly happened. Tell me why, exactly, you don’t want to be with me or what happened to our relationship. If you do that, it would give me closure and allow me to move on. You say that you’re sorry for making me sad and that you want to do anything you can to give me closure, but then when the moment comes to discuss this, you offer vague explanations and don’t really say anything.

I think I’m being pretty clear here, so tell me if I’m not. I’m asking you, please, tell me what is going on in your head and why you feel the way you feel. I feel like to a certain degree you owe that to me. I gave you three years of everything I had.

Also, it’s frustrating when you tell me you need a couple of days to respond and then all you tell me is that you don’t think we can ever be together again. That’s not a huge surprise. The more you delay working this out, the more painful it is for me. I’m exhausted and want this all to be over, but I want to learn and grow from it and try to not make the same mistakes.

Every day that you wait to do this is like torture. Just tell me why so I can move on and we can both move on.


From: Lucy 12/14/14

9:54 PM EST

To: Me

Ok I will try to explain in another email.

Sent from my iPhone


From: Lucy 12/15/14

10:07 PM EST

To: Me

I know that you want an answer but sometimes there is no clear answer. Why did we break up? I can’t really tell you. It fell apart. I had doubts about our relationship before Guam, I felt like something was missing, I couldn’t imagine myself being married to you. Then I went to Guam and I feel like I saw a side of you that I did not like. I feel like you smother sometimes and then maybe I wonder if I’m just cold. You are so caring and supportive. Either way we are not on the same page emotionally. I love you but I am so so so so so tired of feeling like shit about this. I don’t remember the last time that I felt okay. We have tortured each other for too long and I just don’t think that there is any going back. I have felt so much pain and I just want it to stop. I think that the only way to get out of it is for us to not see each other anymore. I swear to god I really hope for the best for you because you are amazing and honestly I probably don’t deserve you. You need to get it through your head that I am not the person you want. That’s another thing is that I sometimes feel like you were so infatuated with me that you didn’t really see me. I realized that I have no idea what your darkest secret is. I don’t think you would feel comfortable telling me. I wouldn’t feel comfortable telling you. I think our communication failed. Actually I know it failed. Even though we thought it was good we just talked circles around each other and you lied and I lied about my doubts because I was lying to myself. Maybe it’s just the place that we were both in. Anyway, it got to a point where I feel like I can’t really talk to you anymore, or I could but it wasn’t getting through.

Also, I have never been in a relationship like this before and have always felt so clueless. Am I making a huge mistake here? Maybe, but I have to make it. So the short answer is I don’t have much to tell you. I’m sorry. I just had this strong feeling that I could not be in this relationship anymore and I feel like now even though I am sad all the time that this was the best thing.

I’m sorry this is so chaotic but you kind of asked for it. This is too hard for me to think about for long. I get so upset I feel sick. I hope that this answers your question.

One more thing: I feel like you are thinking too hard about your role in this. You didn’t do anything WRONG. Sometimes things just don’t work out. This could be all my fault. I do not know. All I know is I’m sorry.


From: Me 12/16/14

10:10 PM EST

To: Lucy

Thank you for at least trying to explain. I think the biggest regret of my life is that I could not figure out how to be the person you loved with all your heart. I couldn’t figure out how to get you to open up to me. I know that I won’t be able to get it out of my head that you’re the person I want to be with because you ARE the person I want to be with. I know I’m over-the-top sometimes with my emotions and I love you so much and I’m so infatuated with you that I tend to smother you. The regret I feel about not being the person that you could love is probably a large part of the reason why you don’t want to be with me and why things fell apart. I’m sorry I’m insecure but I can’t stop myself. I wish I was a different person. I wish I was the person that you could love back and open up to, because I know that I’ll never find anyone as good as you.

With that said, I also agree that it’s best to not do this anymore. At the end of the day, it’s just not meant to be. We shouldn’t be together and we should just move on. There is too much bad history between us, and I’m clearly not the person that you want to be with.

I think part of the reason why this hurts so much for me is that I let you in 100%. I laid my soul open to you and I never felt like you did the same. I could never figure out what was going on in your head and I could never figure out how to get you to really open up to me. I never knew what was wrong when it was wrong because I couldn’t read your mind and you wouldn’t really talk to me. Things got worse and worse when you went to Guam because I could feel the emotional distance, and it made me insecure. I knew that you weren’t invested 100% and that led me to believe you were looking to be with other people and/or were with other people. Because I couldn’t figure out how to get you to open up to me emotionally, I felt like you were lying about factual things too. Still to this day I wonder if you were with anyone else while we’ve been apart. That is what led me to talk to other girls and get very insecure about our relationship. I could feel something was wrong and felt helpless. I knew I was losing you but didn’t know what to do about it. When I went looking for someone else/when I started talking to other girls, I realized how much I loved you and how much I wanted to try to make it work. I wanted to be the person that you wanted to be with even if I wasn’t yet that person. I realize now that was probably the opposite of what I should have been doing. I should have backed off and gave you space to sort things out. I just thought that if I did that, you would want to move on and I’d lose you.

It makes me sad that you say you wouldn’t feel comfortable telling me your darkest secret, but I think that is a good metaphor for why things went wrong. I don’t really have a darkest secret, but if I did I would tell you in a heartbeat. I would feel comfortable telling you anything. I would trust you with my life. The fact that you wouldn’t feel comfortable telling me yours, even after being together for over 4 years, is pretty indicative of the fact that we shouldn’t be together. Again, I wish I could have figured out a way to crack that emotional shell of yours.

I’ll always love you and I’m sorry that I made you explain all these things to me. I needed it in order to move on.

I know you said you feel sick and I feel sick too. I haven’t slept all night and my head has been pounding. We don’t have to continue this any more if you don’t want to. I’ve said everything I wanted to say.

I hope that you find the person that makes you happy and that you can love that person with everything you have. I’m sure you will, because you’re really special. Whoever gets to be with you will be very lucky.


From: Lucy 12/20/14

To: Me

I hope this makes you feel better. Even reading this, which is very hard, I don’t think you understand how I feel. You don’t think I told you everything that I thought? I really tried. Don’t wish you were another person, sometimes it just doesn’t work. I swear to you I never was with other guys when we were together, if that makes any difference.

Anyway in the interest of keeping things short, I hope you know how much I care about you, but obviously it is too hard for me to think about you, so I would appreciate it if you would let it go and we would not talk for now.

Please take care.

Sent from my iPad


Two weeks after that exchange of emails with Lucy, I was hate-fucking Cindy in my lonely one-bed apartment and starting 2015 in the style I had become accustomed to. It’d be nice to tell you that I never looked back. It’d be nice if I was a confident, well-adjusted, emotionally stable person who handled the break up in a healthy, mature way. But I wasn’t that person, and the only place I looked was backwards with resentment and rage burning in my heart. Getting closure for me meant searching for all the ways it was my fault, and I wanted those answers from Lucy. I wanted flagellation at her hands. What about me was not enough? Was I not sweet enough, kind enough, generous enough, thoughtful enough? Was I too awkward? Too antisocial? Too misanthropic? Was it my neuroses? My negativity? My cynicism? Was it my lack of confidence? My self-loathing? Because I was a terrible lay? My tiny dick? My potbelly? My giant head?

Or was there really no reason?

At the end of the day I couldn’t force her to reciprocate my love, and that’s all that mattered. I lost her, and none of the crazy desperate shit I’d already done had gained me any ground whatsoever, so I figured nothing would. I knew she was gone but still couldn’t let go.

Six months later in June of 2015, in the middle of Sky and Brandy and the harem of women I met through the swipe-apps, I reached out to her again. It was one sentence that said, ‘I hope you’re enjoying your new job and I hope you’re doing well.’ She emailed back. She apologized and explained that she was cold and distant during the breakup because she didn’t want to give me false hope. She told me she’d taken a job with a big firm in Palo Alto, and for a moment as I read her email, the anger and resentment bubbled up again. She always told me she was going back to the East Coast, and I’d restructured my life around trying to make things work with her, and ultimately she took a job in Cali-fucking-fornia. But then I thought of Sky, Brandy, and the Florida State M.B.A. student I was screwing, and while they provided me little solace other than the promise of something else, they represented the possibility of life going on. Long overdue for rationality, I finally stopped pestering her and I haven’t talked to her since.

Forgetting Lucy and Creepy Internet Stalking

I read somewhere that only narcissists and sociopaths stay in touch with their exes, and whether or not that’s true, if you’re getting over a breakup the worst thing you can do is stay connected to your ex on social media, because the Internet has provided a creepy level of stalking potential for anyone that knows how to operate a computer. While it’s true that after our brief June 2015 email exchange I hadn’t spoken to her, that doesn’t mean I didn’t know where she was or what she was doing. Brandy Brunette once pointed out that cutting off all contact with your ex was the healthiest thing to do after a break up, and I agree. If you don’t, you’ll inevitably stumble across a group picture of them at some music festival where the Instagram filter is most flattering to everyone, and you’ll be compelled to look at your new competition and think, which of these guys is she fucking?

Or worse, they’ll actually be on a date, or at least what looks like a date, and either the ambiguity of whether or not it’s a date will kill you or they’ll be kissing in a bold way that announces to your face: I’VE MOVED ON AND YOU’RE A PATHETIC LOSER FOR STALKING ME ON SOCIAL MEDIA AND YOU SHOULD MOVE ON TOO.

And you will feel pathetic, because you’ll realize she’s right and you are pathetic.

I’ll admit that I googled Lucy every few weeks for months before realizing I was on track to be a 65-year-old single man sitting alone in my apartment, eating my TV dinner, still googling some girl I dated 30-odd years ago. Finally, I unfollowed her, blocked her, deleted her, and unfriended her. It was the only way to save me from myself.

I would still fantasize about her reaching out to ask how I was doing though, or to tell me she missed me, or to admit she made a huge mistake, or to beg me for a fresh start. In my fantasy I would tell her confidently that I’d moved on or I’d matter-of-factly inform her I was dating someone and it was serious. I’d tell her about how I’d become very successful, or won the lottery, or that I was traveling the world and I’d found eternal bliss as a free spirit. She never did, of course, and thank God I resisted the overwhelmingly strong urge to embarrass myself further. I still think of her on holidays and her birthday. I still miss the closeness and comfort of her, and the memory of how we grew together never fades either.

I’m sure that by the time this book is published Lucy will be married to some cardigan-wearing East Coast snob who makes half a million dollars in finance at some too-big-to-fail bank and collects vintage cars, but I ‘accidentally’ came across her picture the other week on Facebook. The Internet is forever – deleting, unfriending, and blocking only goes so far. There’s always a way to get in touch, and after four years together there’s a hundred different ties that still bound us. When she appeared in a friend’s post, I couldn’t resist scrolling through the pictures, and I couldn’t help but get the slightest twinge of satisfaction when I saw her frumpy dress frayed out at the waist a little more than I remembered – her cheeks were puffier, and her smile a little more faded. She looked like she’d gained 20 pounds and aged ten years.

Then again, I’m sure it was all just in my head.

How to Meet Someone in Real Life

I’ve described in this book how easy and serendipitous it was when I met Lucy, and how our story naturally evolved into love and then spiraled into madness. That’s the point – meeting someone in real life is not formulaic. It just happens. So when answering the question of how to meet someone in real life, despite all the dating advice books and self-help gurus claiming there’s some kind of silver bullet, there’s really only one way: Be lucky.

Be single when they are. Be looking for love when they are. Get introduced at the right time. In the right place. Be looking your best when you first meet. Be your most energetic, vivacious, and charming. Be willing to accept their flaws. Be hopeful they’ll accept yours. Time it right so they accept your shortcomings. Go on dates. Fight through uncertainties. Don’t get hung up on doubts and reservations. Understand that no one’s perfect. Be open to love. Factor in all that shit as well as the ten million other things that have to go right moving forward, but, most importantly, more than anything: Be lucky. That’s what you need to do.

Helpful? No, of course not. But at least I’m honest.

So now that you know how to meet someone in real life, let’s filter through some common dating ‘strategies’ and separate the bullshit from the few helpful pieces of advice out there.

Lock it Down Early

I always thought friends who got married in high school or college were idiots. There are almost 7.5 billion people in the world, and it seems crazy to commit to someone for the rest of your life just because you had a class with them or because you drunkenly made out at some frat party and went on a couple of mediocre dates. I can agonize for hours over decisions like what Netflix show to watch or what to eat for dinner, so it seems silly to choose a life partner on such an arbitrary basis as ‘they were in close physical proximity to me and had great tits and nice clothes.’ But maybe marrying your high school sweetheart is the way to go, and maybe all my friends that met their partners early in life got it right, because meeting someone serious outside your twenties seems virtually impossible. This is especially true if you work a job where you don’t interact with attractive members of the opposite sex (e.g. the U.S. Navy), if you’re not religious (you can’t meet in church if you don’t go to church), and if you’re preternaturally shy and/or anxious (isn’t this everyone?). This is also true if you live in a country town with a population of 200 and your dating options consist of Sally, captain of the two-person cheerleading squad, or Mary, the mathlete who may or may not be your second cousin. If your life circumstances fall into any of those categories, marrying the first person you can tolerate might be your best choice.

I’ve said before that it doesn’t matter how you find your special someone (grocery store, church, online, burglarizing their home), but maybe it also doesn’t matter when you find them. Maybe those friends in college did the right thing – they found someone they liked, they could see themselves together with that person, and they just went for it. After all, how is meeting someone later in life and choosing to be with them any less arbitrary than locking it down with the first person you bat your eyelashes at? In one case you have some life experience and in the other you don’t, but with something as complicated as love, life experience does not necessarily equate to a better outcome.

The Set-up/Blind Date Scenario

After my breakup with Lucy, I had a lot of good friends who took pity on me and tried to set me up. All these situations were remarkably similar, and went something like this: A friend’s wife or girlfriend will say something like, ‘I have the perfect girl for you!’ and she will get very excited about it. She will show me a picture on social media, and let’s say I don’t have to awkwardly feign enthusiasm because she’s being overly-charitable about her friend’s looks. (Women do this all the time.) Let’s say she’s actually quite pretty and I’m impressed. At this point, it’s kind of like a choose-your-own-adventure book where I’m trapped in an M.C. Escher painting with a predetermined fate to end up where I started. A few different things could happen.

1) My friend’s wife/girlfriend will never actually set up the date, and I will feel weird about bringing it up because if I do I will appear desperate, or it will force her into explaining why she realized it was a bad idea and reconsidered.

2) My friend’s wife/girlfriend will come to learn that the blind date has a boyfriend, and I will be devastated.

3) I’ll exchange numbers with Blind Date and we’ll never go out, because, you know, people are very busy these days (read: Fickle), and there’s always hesitancy for people to deal with the awkwardness of a blind date.

4) We’ll both muster up the courage to go out, and whether it’s confirmation bias or the hesitancy to feel like we’re part of an arranged marriage, the pressure of a third party believing in our compatibility will be too much, the date will be mediocre, and we’ll never see each other again.

The Set-up/Blind Date Scenario is hard, because it’s full of hope and optimism but seems to never actually work out.

Get a Hobby

If you’re single, I’m sure you’ve had people say to you, ‘you should get a hobby!’ or, ‘have you ever thought about joining an adult softball league?’ Your friends are not the only ones, because this is also a favorite suggestion of dating ‘gurus’ (read: Professional bullshit artists), and can just as easily be replaced with ‘get out of the house and be less boring you miserable fucker.’ If you’re sitting alone eating a TV dinner every night and hoping that a beautiful single person will come crashing through your skylight and land in your lap, you’re probably going to be alone forever. While it’s true that the more people you interact with, the better chance you have at meeting someone to date, you shouldn’t think ‘getting a hobby’ is a magical antidote to immediately get you hanging out with attractive sex-starved singles.

For instance, if you join a chess club without really liking chess, you could end up sitting around playing chess with a bunch of geeks that jizz their pants at the mere sight of a pretty girl. It’s true that you might (and I mean ‘might’) meet the love of your life, but joining a chess club didn’t increase your odds any more than walking out of your house, blindfolding yourself, and striding into oncoming traffic with an erection in hopes that a good-looking single person hits you with their car and takes pity on you. Or let’s say you join a gym and that you wouldn’t normally be caught dead in. If you’re a woman you might end up meeting some muscle-bound caveman that can help you get massive gains in your biceps but can’t name the current President – not exactly an ideal match. Or maybe you take sailing lessons and meet someone named Chet or Margaret that actually thinks caviar tastes good. You might be able to double-date with Lucy and her future husband, but have fun groaning over politics at an overpriced restaurant with a bunch of people who need lessons on how to have fun.

Joining a goofy softball league or taking a painting class are only good ideas if you want to do them in the first place, and you shouldn’t go into any of those activities with your primary goal being to get laid. Getting a hobby or joining a club isn’t a dating strategy; it’s a tip to get you off your fat ass and out into the world. So go ahead and join a club or a team, but you’re just as well off taking a walk around a city block during happy hour.

Stop Trying

This is the worst, dumbest advice on dating anyone has ever given.

Sometimes people trot out the advice of ‘once you stop trying (or looking or hoping or thinking), you’ll find someone.’ That makes no sense. It’s not like the second you stop looking, someone magically appears who you’re perfectly compatible with and ready to date. The point of this advice is that if looking for love and not finding it is making you miserable, then you should stop looking, or at least you shouldn’t despair when things don’t work out. ‘Stop trying’ is really just a Jedi mind trick to prevent you from feeling emotionally crushed by the seemingly futile exercise of dating.

If you’re a man who never asks women on dates, you’re going to be alone forever. I’ve said it a hundred times and I’ll say it again – dating is a numbers game, so if you stop trying, you might as well chop off your twig and berries and become a eunuch. Tricking yourself into not caring about love might prevent you from feeling the constant pang of rejection and/or loneliness, but it’s not going to help you find love. A romantic vision of serendipity guiding you to your perfect partner is not realistic, and if you stop trying to find love, chances are high you won’t find it.

Which bring me to the best, easiest way to meet someone without using the swipe-apps, but one that gets much, much harder as people age.

The In-person Introduction

I met Lucy through a mutual friend in a purely chance encounter. Again, I just got lucky, but the scenario was ideal. An In-person Introduction is different than a Set-up/Blind Date Scenario because you’re already out with friends and you get a judgment-free introduction to the person, but if there’s no spark you just shake hands at the end of the night and say goodbye. This is the best way to meet people, it’s just that it gets harder and harder as you get older. The most attractive bachelors or bachelorettes have been snapped up, many eligible singles have already been through one or two divorces (perhaps they were a child bride previously wedded to a Special Forces operative), and most of your friends ensconced in relationships are staying home on Friday night to cuddle on the couch, have quiet sex, and go to bed at a reasonable time. They’re not exactly eager to be your wingman/wingwoman. The benefit of third-party validation, the diffusion of awkwardness by having other friends around, and the naturalness of the In-person Introduction make it the best strategy, yet even in this most perfect of climates you still have to get lucky. And if you wait too long to find a mate, just getting into the above scenario becomes as probable as hitting the Powerball.

The Silver Bullet for Him and Her

As a reminder, there actually are sure-fire ways to find a date for both men and women. Here they are:

For him: Be rich (the richer, the better). If you have money and flaunt it, women will flock to you like flies on shit.

For her: Be attractive (the more attractive, the better). If you’re attractive, you were probably born with a boyfriend and you will never have to worry about finding a date.

Love and Loneliness

Love and loneliness are pitted against one another in virtually every aspect of society, and sometimes I wonder if it’s better to just settle – find anyone halfway decent and get on with the business of compromise. Maybe the important thing isn’t to find someone who’s your soul mate, but rather it’s enough to find someone who’ll just keep you warm at night. (And that you don’t want to murder.) Other times the loneliness is too much, and I think about Lucy and how nice it was to have someone to keep you warm at night who you also feel a deep connection to.

Is it better to be unhappily wedded or unhappily lonely?

Sometimes marriage looks like a dangerous game of roulette, because how well can you really know another person? What if, ten years into marriage, I realize I can’t stand her laugh? Or she gains 30 pounds? Or she starts binge-watching The Real Housewives TV show? Or worse, what if she grows to despise me? I’d rather be alone than end up as a plotline from the movie Fatal Attraction. Alfred Lord Tennyson said ‘‘Tis better to have loved and lost than never to have loved at all,’ and maybe I’d have been better off not knowing about love at all. But the poet Thomas Gray also said ‘Ignorance is bliss’ and many people hold by this, so which one is correct?

I only yearn for the feeling of love because I know now how powerful it can be, and if you told me I could go back to that Halloween night in 2010 and lose all the joyful memories of being in love for three years, but also not suffer all the pain of losing Lucy forever, my answer would be: ‘I have to think about it.’ And I would probably never get back to you, because it’s a choice I’m not willing to make. The memories of falling in love with Lucy were irreplaceable, and when I think about the good times, I’m reminded that she was the only person who made me feel intoxicated for life. I’m glad I found love, I’d just like to forget all the bad parts. Especially because the frustration of finding someone new – the seemingly futile effort of looking for a comparable emotion in a random stranger – sometimes seems impossible.

Part Two: Atonement


The further addicted to social media I became while using the swipe-apps, the more I saw the term ‘fuckboy’ appear. Internet celebrities would make jokes about ex-boyfriends being fuckboys, female swipe-app daters would frequently include ‘no fuckboys’ at the end of their profile biographies, and I’d stumble across Internet memes commenting on someone being a fuckboy. After the traumatic couple of months with Alyssa, I retreated to my Oceanside apartment and decided to do a little research.

Urban Dictionary described the moniker as ‘A person who is a weak-ass pussy that ain’t bout shit,’ and included other definitions such as ‘The fuckiest of the fucks, a ‘fuckboy’ is the lowest possible form of the vile, degenerate waste pouring from the proverbial asshole of society,’ and ‘A fuckboy is a guy with the body of a man and the mind of a perverted teenager. He has no heart – just a penis that he uses to paint the town.’

Well, thanks Urban Dictionary for being that reliable paragon of academic rigor that we’ve all come to rely on so heavily. If you’re looking for a totally worthless, grammatically suspect dictionary definition by some random idiot with nothing more than an opinion, look no further than Urban Dictionary. (Keep in mind that this was the top google search result.) The less popular definitions on Urban Dictionary (there are currently 93 pages of fuckboy descriptions) were actually a little more instructive: ‘A manipulating dick who does whatever it takes to benefit him, regardless of who he screws over. They will screw over anyone and everyone as long they get what they want.’ Personally I don’t know anyone like that.

Despite the fact that online journalism seems to have devolved into college kids blogging from their dorm room in their underwear, a slate.com article made the cogent point that the term is really undefined, and there are many definitions. Finally, a Vanity Fair article provided something resembling insight. In ‘Tinder and the Dawn of the Dating Apocalypse,’ Nancy Jo Sales writes,

A ‘fuckboy’ is a young man who sleeps with women without any intention of having a relationship with them or perhaps even walking them to the door post-sex. He’s a womanizer, an especially callous one, as well as kind of a loser. The word has been around for at least a decade with different meanings; it’s only in about the last year that it has become so frequently used by women and girls to refer to their hookups.

Sound familiar? It did to me. Ms N.J. Sales’ definition was illuminating, except that ‘kind of a loser’ didn’t seem accurate, because after months and months of promiscuity, manipulation, and self-loathing, I felt like a total loser.

Fuckboy as a derogatory epithet was both a useful description and staggeringly accurate assessment of my situation, but if the purpose of an epithet is to denigrate the subject it’s directed at, it failed miserably. That’s because to the fuckboys go the spoils, or so it seemed. I might have been depressed and lonely, but I had a rollicking good time in the process because I was finally getting laid. I had more confidence than ever. Women treated me differently. I felt like a new person. This wasn’t much more than a simple confirmation of the age-old truism that most women like assholes, because I’d become a gold-plated diamond-studded asshole. The same Internet celebrities who posted jokes about fuckboys and the female swipe-app daters asking that fuckboys need not apply seemed to be falling for, and most interested in, the womanizing, callous male lovers that Ms Sales described.

If you can’t beat ’em, join ’em, and that’s what I did (as depressing as it was).

The Fuckboy in the Bedroom

Even more disturbing than who I’d become was what I had learned. Women’s attraction to fuckboys disturbed me, but the cavalier hobby of sport-fucking illuminated some scary truths that I wish I never learned. With Lucy, I was gentle, tentative, and even nervous lover, because I didn’t want to do anything to upset the aura that led to us getting naked in the first place. But from the dozens of women I slept with in the forthcoming months, it became clear that assertive aggression was the behavior they overwhelmingly preferred. In fact, many specifically requested I get aggressive with them. I obliged, and it freaked me out.

During my first one-night-stand with little red-headed Cindy, I gently laid her on the bed, interlocked my fingers with hers, and slid my rock-hard cock inside her. Straddling her, with my hand on top of hers, she wrapped her free arm around me and said, “Pin me down.”

I did, and she screamed out, “Fuck me harder. Pull my hair. Slap my ass.”

When we were finished she reminded me, “I like it rough.”

Cindy wasn’t alone. Alyssa also liked it rough, and when she closed-fist cold-clocked me while I was still balls-deep in her, I knew this was the height of depravity. She wanted to be choked, aggressively fucked in the ass, tied up, double teamed, ejaculated on, and apparently enjoyed punching me in the face while I did it. And I did it all. I was rough as I thought she wanted me to be. Yet even months later she still asked,

“Will you be rough with me in bed?”

“Aren’t I already rough enough?”

“I want you to get really rough.”

“What do you mean?”

Saying nothing, she was clearly going to make me guess.

“What? Like beat you up?!”

“Yeah. I think it’d be fun.”

No fucking way, I told her.

Maybe I have a very puritanical view of sex, and I’m clearly not the type of person who would ever get into proper BDSM, but hitting a woman under any circumstance is crossing the line (unless she’s about to stab you with a knife). Alyssa wasn’t alone, because even the most seemingly innocent women I met on the swipe-apps would still want to be roughed up a bit. It seemed like the hotter the woman, the more she wanted to be fucked like a drug-addicted prostitute. It felt kind of unsexy, but it was hard to say no when they specifically requested it so I gave it my best shot.

As a Navy JAG, I’d spent my professional career observing questionable prosecutions as well as very serious, slam-dunk cases that evidenced clear, inexcusable guilt. Congressional pressure to clean up sexual assault in the military led to a lot of dubious cases going forward to court martial, and drunken, regretful sex could lead to years and years in prison, based on nothing more than the testimony of one person and a very shitty Navy Criminal Investigative Service investigative report. So when women asked me to get physical with them, I’d break into a cold sweat. Should I not honor the request and go back to being lonely and miserable? Or should I do what she asks, and be the fuckboy in the bedroom she’s apparently always longed for? I’d seen many prosecutions turn from consensual sex to sexual assault in the blink of an eye, and the slightest miscommunication between partners could mean a lot of jail time. With only two people in the room, all you need is one person’s testimony to convict. Every sexual encounter, no matter how much explicit consent I obtained, felt like an enormous risk.

I’m not going to pretend like I’m such a puritan that it wasn’t really fun at times, because rough sex does add a layer of thrilling titillation to getting your rocks off, but the commonplace requests for nasty variations of intercourse got me thinking, Can’t we just enjoy ourselves with nice, quiet sex, watch TV, sleep in separate beds and I’ll make you breakfast in the morning? Is my future wife going to want to do this type of shit? More importantly, Do I want my future wife to want to do this type of shit?’ I couldn’t picture myself as a suburban father, knocking on my neighbors’ door to see if they had a length of twine or a curling iron and a coat hanger, and then asking them if they’d be interested in joining in a gangbang with my wife and me. One day my insatiable life partner and I would take autoerotic asphyxiation too far and the police would find us hanging from the ceiling fan.

That’s not how I want to die.

The Fuckboy and Relative Indifference

The psychology behind relative indifference is about how it’s a more powerful urge to want than to have, and making your partner work for you increases your value in their eyes. It makes intuitive sense – people want what they can’t have. Unfortunately, rewarding indifference means men are more likely to be promiscuous, because it’s hard to be indifferent unless you believe other options are available. Before the swipe-apps, I thought Lucy was the only person in the world for me, and I thought there were no other options (nor did I want there to be). So I suffocated her. Once I got on the swipe-apps, I had so many options available to me that I didn’t care if someone unmatched me or didn’t call back or went on a couple dates with me and we drifted apart because they lost interest. I didn’t care that much if they actually liked me – because there were always another options available. I was a fuckboy.

Women want a fuckboy’s personality without the man fucking (or even wanting to fuck) anyone else. So when disgruntled women and jaded nice guys can use the term fuckboy pejoratively, the fuckboys get the last laugh because they’re still the prize. The question now is, who should I become? Should I be a game-playing, alpha-male fuckboy that is callous and indifferent to women, but gets laid? Or should I be the gentle nerd that is tentative, over-extends himself the second things start going well, and repulses women because of it? I know that ‘somewhere in between’ is the correct answer, but the emotional navigation required to achieve that balance is very difficult for me to pull off, and if the uber-confident, totally indifferent fuckboy is such an easy default, why go through the trouble of even trying?

Here’s an answer: How about women just stop preferring fuckboy douchebags to nice guys, and I won’t worry about acting in a way that I loathe.

The End to My Internet Dating Life

After Alyssa, I headed back to despair but persisted in using the swipe-apps. The more I swiped, the more I matched, and the more disgruntled and disillusioned I became. I swiped right looking for despair; I swiped right looking for companionship and found nothing but loneliness. I found women I didn’t really want to be with, couldn’t really see myself with, in relationships that I continued to treat like cold, impersonal transactions, nothing more than notches on a bedpost. Despite my high confidence and success rate, my misery persisted.

In July I was in San Diego for some Navy JAG training and matched with 25-year-old Emily. After going through the paces of chatting, messaging, and meeting up for drinks, we went back to my hotel room and for the next eight hours she proceeded to drain me of all bodily fluids. She had full lips that I found out later were actually full of Botox. Her C-cup breasts I knew right away were fake. She didn’t have an ounce of fat on her body, and her long, muscular legs joined at the hips like that of a bikini model. She also had a thigh gap, which was all the rage with idiot females at the time. She was the kind of woman I’d watch on the Internet in the cramped spaces of my teenage bedroom and be mesmerized by as I masturbated myself into a frenzy.

We went through the same exhausting repetitions of two strangers who knew their way around in bed but barely know each other. First fellatio, then sex. I came. She came. I came. She came. Rinse. Repeat. After our first couple of rounds of sex, I thought I was done, but all she needed to do was rub her sexy little naked body against mine and I would get hard. Just more and more empty, boring sport-fucking. We did it again and again until neither of us could stay awake any longer. Nothing can explain me having the sexual stamina of a 16-year-old other than the fact that the urge for self-destruction is extremely powerful, and I was on a mission to hit my absolute rock bottom.

I awoke the next morning to her on top of me. She put my semi-hard penis inside her, groaning loudly as my cock hardened, and I wanted nothing more than to just be alone. When we finished, I told her we had to leave, and I went to work. I sat in training and meetings all day, thinking about the misery my life had become. Then my week in San Diego ended and I returned to Oceanside.

Just like Alyssa, Emily had absolutely no problem sharing the most sordid details of her past and the stories were so good that continuing to text and call her despite the distance became a morbid, perverse research project. She told me how a few months prior she’d been on ‘Seeking Arrangement,’ a dating website designed to set up rich older men (aka Sugar Daddies) with young, desperate women (aka Sugar Babies). It was the same website Alyssa’s sister used, and it was basically legalized prostitution. Through that website, Emily had had multiple threesomes with a 42-year-old divorcé real estate developer and his girlfriend. Mr Real Estate would fuck Emily in the ass while Emily licked the girlfriend’s clit. Then there was a general contractor who wanted to fuck her exclusively in the ass, and did so many times, followed by a desperate middle-aged doctor who used to get on-demand blowjobs.

Each encounter earned her a few hundred bucks, and after my one night with her and seeing how beautiful (albeit fake) she was, I couldn’t help but think she should have gotten more. Over a period of about a year she slept with a dozen different men she’d met through that website, and had a half-dozen ‘regulars’ that she catered to. She stopped charging Mr Real Estate, justifying her decision by calling him her boyfriend, and even admitted to having sex without a condom a couple of times. She told he how she stopped asking for money because she ‘felt bad.’

We texted for a few more months, and the stories weren’t the only cause for alarm. She sent me an impressively varied collections of nudes, some extremely close up and gynecological in nature, as well as fairly unambiguous messages like, ‘I want you to fill me up with cum.’ And then it got really bizarre when she admitted, ‘I want you to get me pregnant.’ She told me all about her fantasy for us to have a family together. So once again I had gone looking for depravity and perversion, and I’d found it. I’d reached a new low, and I deleted all the swipe-apps once again. If my Achilles’ heel is not learning from my mistakes, dealing with Emily – the former sugar baby/prostitute who was begging me to impregnate her – should be enough, and it was, because this time there was no going back.

What I Learned

Perhaps I’m doomed to repeat the same mistakes over and over, and I learned nothing in this whole sorry process, but I’d like to believe that some reflection is a good thing, so here’s what I think:

My Friend Collin

For all my crude, mean-spirited talk of stodgy prudes and Bible-thumpers, sometimes I wonder if they have it right, because many of them seem to have the assured confidence of Zach or Jason Sudeikis without being a cheating womanizer or a B-list celebrity. Even if the assured confidence is misplaced in a doctrine that is false and totally unverifiable, it must be nice to get that confidence from somewhere. It’s not necessarily a trait for all of them, because sometimes it’s manifested in an obnoxious know-it-all preachy way that consists of never ending streams of nonsense and bullshit pouring out of their mouths, like ‘God is Love’ or ‘God is Light,’ and that shit is deeply offensive. I want to punch those people right in the face. But sometimes it’s a quiet confidence that is a comforting, warm presence, like they have a great secret they’re more than willing to share if you just listen a while.

That describes my friend Collin. He doesn’t ram religion down your face, he just tells you what he thinks, and he does it with believable conviction. Collin, like a lot of these religious types, waited for marriage before he had sex, and he was never burdened by the same curiosity as me. He spends most of his time in an everyman way – with his job, his wife, raising a family, etc., but unlike me he seems perfectly happy. It doesn’t bother him one bit that he’s only had sex with one person, and he doesn’t dwell on all the people he might be missing out on. In the middle of my sex rampage, Collin remarked to Will that the problem with sleeping around was that I wouldn’t be able to un-ring the bell of all the debaucherously perverse sex I’d engaged in. Speaking of me, Collin said, “When he’s with his wife, he’s just going to be thinking about all the other women he’s been with.”

He’s not entirely wrong. As crazy as she was, how can I not forget Alyssa demanding that I fuck her in the ass? The crazy nights of wild sport-fucking? Her screaming my name out in ecstasy? How can I not forget Emily’s perfect tits? Perfect lips? Even if they were fake?

So here’s the question: Is Collin right? It goes back to the belief that ignorance is bliss. Maybe not knowing all the options out there is the way to go. The flip side is that whatever depraved urges or sexual adventure I sought, I found, and maybe I had to get that out of my system. I satisfied my curiosities, and maybe instead of thinking about other women I’ve been with, I’ll know that I’ve been there, done that, and that the empty pleasures of the flesh don’t lead to anything lasting. I’ll be satisfied knowing through experience that when I have something real with someone, it’s not just enough, it’s better. There’s no right answer, and it doesn’t help me now but you should make that decision about yourself before you walk down the same path I did, because you can’t rewind history.

What You Want and What You Don’t Want

It’s obvious that I met a lot of women on the swipe-apps. I was in a lot of different situations, under a lot of different circumstances, and while I used to think there was a certain person I was looking for that fit certain characteristics, I know now that anyone who does that is an idiot. Dating is hard because you often don’t know what you want until you have it or, in my case, until you’ve lost it. You might require your mate to be a marathon runner who used to model underwear and only listens to country music, but if you’re limiting the people you’re willing to meet using stupid ‘deal breakers’ like those, you’re going to be alone forever because those types of things are just preferences and they’re not actually deal breakers at all. Even traditionally polarizing issues such as politics or religion can be overlooked or compromised, so long as both people have an open mind to the other’s point of view. On the swipe-apps everyone is too picky, because it’s so damn easy to be picky. With so many choices available, you don’t feel like you’re missing out if you swipe left on someone who reads Dan Brown novels because you think Dan Brown writes at a third-grade level. And if you think someone’s enjoyment of Dan Brown tells you something profound about them, you’re probably wrong. It might be telling, but it might not. Just because they want to read a candy-bar book does not mean they’re a bad person, and you don’t really know if it’s going to work until you go on a date with them and eventually really get to know them. While it’s easy to exclude someone on very specific criteria, what you think is a big deal probably isn’t.

There are very few exceptions to this rule, and unless you’re requiring the person not be a member of the KKK or not be a Russian spy, you’re probably being too narrow-minded. Height compatibility can sometimes be a legitimate issue, but only if you’re freakishly tall or freakishly short. If you’re a 5’8” woman and you are requiring your dude to be over 6’, you’re probably missing out. Finally, I’m going to go ahead and make the call here that racial discrimination is sometimes okay in dating. Maybe you’re a terrible racist bigot who should be burned at the stake, but if you’re not attracted to Alaskan Eskimos or anemic Scandinavians then I think it’s fair to refine your options in that way. Although, have you seen an Alaskan Eskimo? They’re fucking dope. And hot, sometimes.

I learned some lessons about what I want, and what I don’t want, but I learned them through trial and error: I don’t want a woman who punches me in the face during sex. I’d prefer it if she wasn’t a former child prostitute. I’d rather not wait to get married before we have sex, and I don’t want a woman who thinks it’s okay to toss my belongings in a dumpster under any circumstances (okay, maybe some circumstances, but very few). Most of all, I want someone who can be made happy, and who I can make happy. Maybe it’s sad that it took me years of my life to realize it, but if no amount of butt plugs, vibrators, or cock rings will ever satisfy her sexual desires, she’s not for me. It turns out I’m better off with someone who’s not a nymphomaniac, but who will be okay with keeping things fresh in the bedroom (see graph below).

Faults and Imperfections

Remember my giant head? My potbelly? My tiny penis? My neuroses? These things haven’t gone away, I just started looking at them differently.

The first night I met Courtney (the smoking-hot porn-star-looking vixen that was also really cool), a group of us had rented a party bus for the winter holiday. After we were all smashed enough to have the kind of indecent drunken conversation that turns heads and gets you kicked out of places, we started talking about sex. Courtney’s friend Kacey remarked that her boyfriend was not fucking her hard enough, and it was driving her crazy. I thought Kacey was pretty, the booze had destroyed the brain-to-mouth filter people are supposed to have, and I was right in the middle of my sex rampage, so my confidence was at an all-time high. I looked her right in the eye and told her I would love fucking her, and that if she wanted me to fuck her hard, I would. I’d fuck her any way she wanted me to.

“But, there’s one thing,” I said. And I hesitated. She asked what it was.

“I have a small… uh—”

“Doesn’t matter,” she cut in. “As long as it’s not a micro-penis, it’s not always about that.”

I’m sure she was saying this just to make me feel better, but I think to a certain degree she’s right, and while I ended up sleeping with Courtney that night, I appreciated what Kacey said. There are some women out there who will refuse to sleep with men unless they have a giant horse cock (Chelsea Handler), but for the most part, an adequate size is enough. Faults and imperfections that we think are devastating are not considered as that extreme by other people. And these faults and imperfections can be minimized or erased by simply having confidence.

I didn’t do well on the swipe-apps because I had fixed all my problems – I didn’t purchase a penis pump, get liposuction, or take pills to shrink my giant head. On the contrary, I was an off-the-rails train wreck headed for self-destruction. Instead, I did well on the swipe-apps because I didn’t get consumed by my problems. I tricked myself into believing that I was the best version of myself, or at least that my faults didn’t matter (alcohol helps to create this belief system, at least temporarily), and because I was attractive in my eyes, women saw me that way too. So even though I’m gagging at the thought of sounding like a self-help book, it’s important not to dwell on your faults. You might think they’re a big deal, but they’re probably not.

Heartbreak and Perspective

When things ended with Lucy, I lost all perspective. The angry person who carried out a two-year sex rampage might have had some wild experiences, and might have added a few notches on the old bedpost, but as I write this I’m in the same place I was when I started – alone. Thus, if you wind up like me and get your heart broken for the first time, try, try, try to maintain some perspective. Lean on family and friends. Do activities. Better yourself. The clichéd advice to not rush out and try to find someone new right away is actually advice worth taking, and I never thought it made any sense until I lived through it. If you try to fill the void the absence your former lover created, you’re not going to be in a healthy place to do so. You’re going to spend two years on the swipe-apps sleeping with anyone with a pulse, and be no better off for it – just like me.

A couple months ago an attorney colleague lost her husband in a motorcycle accident. They were both around 27-years-old, and they’d been married for two years. I could not imagine being still in the newlywed phase, enjoying life as a young couple, and losing my betrothed in the blink of an eye like that, and as I was talking with my other JAG Corps colleagues about our newly-widowed friend, I felt very selfish for thinking I deserved some sort of love from someone. Here were two people in love that had found it at such a young age and had it ripped away, yet this freshly-widowed friend handled it with grace. So I thought, if this poor woman could get over the death of her husband, I could get over one stupid heartbreak that was probably all my fault anyway. She has to carry the baggage of that grief forever, and she didn’t do anything to deserve it. Meanwhile, I’m whining because I was indecisive at the wrong time, I chose the wrong career path, and my partner didn’t love me back. I was complaining about a garden-variety breakup just because I felt like I was the center of the universe. If my colleague could move on, I could too. That’s life. You can’t change the past and you can’t avoid heartache, even if it’s the worst kind, so there’s no use getting angry about it. Moving on is a choice.

Rejection and Depression

I have a friend that was on the swipe-apps and had to delete them because, as he told me, despite constant right-swiping on any woman with a face, he would go weeks and weeks without a single match. I might have pretended to know what made me an attractive swipe-app candidate, but who knows? Maybe it’s that I’m a lawyer, and women thought I made a lot of money (I don’t), or maybe it’s that I’m above-average height, or maybe it’s because once in a blue moon I say something mildly humorous. I don’t know, but if you think getting rejected in real life is difficult, coming up empty after weeks of swiping on the swipe-apps is especially difficult. Swiping for hours, days, weeks, and months, and then seeing the screen that reads, ‘I’m sorry, there’s no one available in your area,’ is a really good way to make you feel slightly suicidal/homicidal, and the screen might as well say, ‘I’m sorry, no one thinks you’re attractive or desirable, you’re going to be alone for the rest of your life. And you’re a piece of shit.’

So be careful, because the swipe-apps can make you depressed, and if they start to do that you need to have the courage to delete them. They can feel like a game, where the goal is attaining as many matches as you possibly can, and if you don’t have a Gay Friend James or you’re not photogenic, you can feel really, really bad about yourself. Remember two things: 1) people are inordinately picky on the swipe-apps (and online dating in general), and 2) validating yourself through bullshit online social media is toxic behavior. It’s not unlike Facebook or Instagram-stalking where you look at the coolest, prettiest people taking the coolest, prettiest pictures, and then feel like shit because you’re not that pretty and your life is not that cool.

Don’t despair if you’re rejected or you don’t like your options, just go somewhere else. The world of dating would probably be a better place if we could go back to the Dark Ages, before cell phones or even the Internet for that matter. There’d be less games, no more ‘ghosting’ people, less temptation to constantly ‘trade up,’ and nobody feeling like shit because they are matchless after six months of frantic swiping. People could get rejected like they did before the Internet was invented: To their face.

Regret and Living in the Past

Here’s another piece of advice: Live less in the past. I spend a lot of time thinking about times gone by and dealing with regret, and I’m slowly starting to realize that it might not be the best use of my time. Regret solves nothing, and usually just results in beating myself up over all the things I did wrong. Maybe it feels good in a self-destructive way – dwelling on old sins is a special form of punishment – but after cycling through my regrets of the last few years, I realize there’s a fine line between nostalgia, regret, and just plain memory.

For instance, take asking Lucy about her sex life. Getting my rocks off over how many men Lucy had been with was pretty pathetic, I’m embarrassed I ever asked those questions, and it’s painful to me that I know the answers. Even if your future spouse who you love with all your heart has been gang banged in a pornographic video, you should not be inquiring into his or her sexual history. The only thing you need to know is if they have an STD or AIDS, and if it turns out they were banged by the football team or were one of the stars of Two Girls, One Cup, you’re going to have to deal with it once you find out, however that may be. There’s no sense and no use in going searching for information you don’t really want or need to hear. Did I really learn anything from prying into Lucy’s sexual history? Was that really a good use of my time? No. And I think about it every day, and what a moron I was. But maybe the mildly therapeutic effect of punishing myself through regret is the point. Then again, wallowing in regret solves nothing. It might feel good, but you can take it too far, because playing out a million scenarios in your head and beating yourself up over things you did wrong doesn’t change what’s already happened, just like crying over someone who’s died doesn’t bring them back to life. People die, and sometimes things just don’t work out.

Quiet Desperation

So faults are overrated, persistence is key, depression is a sign you’re doing it wrong, regret has its limits, and finding what you want takes time and experience. In the short term, dating advice changes nothing, yet every decision I’ve ever made in my adult life was to improve my chances of getting women to sleep with me, and I fear that among men I’m not alone. It seems I’ll be plagued with quiet desperation for female companionship for all of my days, and I know my childish obsession with finding a beautiful woman to fall in love with is sad and pathetic, but it also doesn’t seem like it’s going to go away any time soon.

I’m only 32, but the older I get, the worse it becomes. That’s because coming home after a long day of work at a job that you’re not really passionate about, eating a TV dinner by yourself, Netflixing a few shows, and then passing out while cuddling with a body pillow, all so you can wake up the next day and do the exact same thing again, is the reason why people persevere through bad dates and countless hours on the swipe-apps. Being alone sucks. Yet if my parents are any example, settling seems just as dangerous, and you could end up divorced from your doctor husband or nurse wife because you found out they were fucking someone else in the medical profession or wherever. Also, the quiet desperation of being in an unhappy marriage is stronger than the desperation of searching for love, so one last key is to have patience.

There are a lot of reasons why I continue to lead the life of a bachelor, and I think they’re symptomatic of a lot of us out there. First, there’s too much choice. I can’t decide between the plain, Ivy-league educated doctor and the vapid, surgically-enhanced bikini-wearing Instagram model (and nine times out of ten, when do decide, I find that neither is very much interested in me). Everyone is more inclined to go solo, even if it means they are unhappy doing so. Women have the same dilemma. They can try to marry rich; they can find their soul mate; they can wait for the right combination of romantic factors to come together so they can have their storybook romance; or they can focus on their career because they’re an independent woman and they don’t want to rely on a man to support them. There are so many choices in life and love that it’s hard to know when is the right time to settle down, and with whom.

Second, I’m too judgmental. I don’t know if it’s my personality and I’ve been this way all along or if this is something that just happens to people when they get older, but it seems like probably the latter. When I meet someone I’m too eager to look for their flaws, because I can’t help but think about all the women I passed on who just weren’t quite right. Naturally, everything is a comparison, and I can’t help but compare the next date to all the others that came before. I’ve waited this long, so the one person I finally choose better be perfect (or so I think). You might have noticed that I’m not so great at taking my own advice.

Third, I’m too selfish. I’ve been alone for so long that now I’m set in my ways. Relationships are all about trust, understanding, and being unselfish, but the older you get, the harder it is to budge from whatever habits you’ve created for your life. The more experience you have in love and life, the harder it is to adapt your habits and patterns to someone new. Sometimes I despair that being gun shy at an early age might have cost me my opportunity to find love, and that I’ll never meet someone who doesn’t have significant baggage, who’s already lived their young adult life by getting married and having kids. But what am I to do about this now? The answer is nothing. I made my bed, and now I must lie in it.

After the heartache of losing Lucy and my adventurous two years leading the sex life of a male prostitute, I realize that I miss the person I used to loath – the guy women described as ‘nice.’ I miss the butterflies in my stomach when I meet a beautiful girl for the first time, I miss my timidity around her as I try to work out whether or not she likes me, and I miss the anticipation and excitement of early dates that don’t turn physical right away. I miss waiting, the figuring each other out, and being nervous. I miss the experience of being inexperienced, and I miss being able to meet a beautiful girl without immediately wondering what it would be like to fuck her.

I haven’t been described as ‘nice’ in two years now, and I wouldn’t mind hearing it again. I hope the last four years of my life haven’t turned me into a permanent douchebag fuckboy, and I hope I can re-kindle that person who isn’t the alpha-male asshole that has a catalog of nudes on his cell phone and brags about his sexual conquests to buddies at the bar. I’m off the swipe-apps for good this time, and I’d like to meet someone in person who isn’t all over me like a fat, clumsy stripper.

Life Goes On

Scott, one of my closest friends, called me the other week and told me he had proposed to his girlfriend. He asked me to be the best man at his wedding, and I told him that nothing would make me happier. His fiancée Jennifer got on the line and mentioned that she had a friend she wanted to introduce me to. She told me all about her and said we’d be the perfect match, and maybe we could meet before the wedding. I told her that it was okay, that I was in no rush, and I didn’t want to force things, but that I’d be excited to meet her when the time came. As we finished up the call I thought about all the ways the situation could go wrong. I worried about how I needed to be ‘on’ when I met her. I worried she wouldn’t want to meet at all. I worried she wouldn’t like me when we finally met, if we actually ever did.

When I hung up, I reminded myself how silly I was for being so neurotic. I stopped running through all the potential catastrophes and realized it just wasn’t worth dwelling on. There’s no formula to love, I thought. There’s no promise of the perfect person, there’s no preferred method to meeting someone, and there’s no formula for when you do meet someone and something clicks. Whether using the swipe-apps or not, you have to be open, you have to be kind, you have to be patient, and you have to get lucky.

I jammed my phone in my pocket and smiled to myself at the thought of being Scott’s best man. With each passing day, the last few toxic years were becoming more and more of a distant memory.

I might find love and I might not. I just have to get lucky.



Swipe Right For Loneliness

A memoir of sex, love, and dating on the swipe-apps. But mostly just sex. From the book: “There’s nothing unique about a love story where someone gets their heart broken, but there is something unique about the way I responded: After I got my heart broken, I went on a hedonistic, unrestricted sex rampage of truly epic proportions. No one comes out of this story smelling sweet.”

  • ISBN: 9781370542321
  • Author: S.D. Gately
  • Published: 2017-05-06 17:50:19
  • Words: 78385
Swipe Right For Loneliness Swipe Right For Loneliness