i'm obsessed with women and tired of pretending i'm not
on kissing girls, feeling small, and hitting the books
In high school, all I wanted was a girlfriend.
God, I wanted a girlfriend so bad. I wanted to hold her hand, buy her flowers, play with her hair. I wanted to kiss her like Will kissed Lyra in The Golden Compass: Magical. Monumental. Mending the tears in a fractured universe.1
But I was a small, skinny little kid who was too scared to talk to girls. Once, as a dare, I asked out a girl I liked… and literally ran away before she could respond.2 I was a coward.
I used to practice kissing my pillow at night. I’d pretend it was a girl and just go ham on that thing. I also practiced on my hand. I’d heard this piece of kissing advice: say the letter ‘H’ (aytch), and during the ‘chh’ sound, that’s the shape and firmness your mouth should be when you kiss.
But I turned 16, still without my first kiss, and I got a little desperate. So I turned to the internet for help. Here’s the exact Reddit post I found (yes I saved it):
I used the advice on a girl in my class: Lucy, who was pretty, blonde, and way out of my league. We got to talking.
One day, the weather was especially nice, so we had Chemistry outside. The class sat on benches in the courtyard, yapping and pretending to read the textbook. I sat with Lucy. She was playing with her ring and dropped it, so I picked it up.
“Propose to me.” She demanded.
I swallowed my nerves.
“Will you be my girlfriend?” I laughed, feigning confidence.
“Sure,” she laughed, not taking me serious until I’d gone home and changed our Facebook status to ‘In A Relationship’.
But now that we were Facebook Official, she couldn’t back out. And I could finally do all that romantic shit I’d dreamt about: I bought her flowers (orange, her favorite) and held her hand while walking around the mall. We even got caught playing footsie under the table in class. But I still hadn’t kissed her.
We’d been dating for a month, and she was beginning to think it would never happen. Really, I was just nervous. Really, really nervous. A kiss was a Big Deal: it’s the gateway between the Romantic and the Sexual, an unambiguous expression of physical desire. What if that desire wasn’t reciprocated?
But the Reddit post was clear: you have to take the risk.
We were lying on a grassy hill behind the soccer field one night after practice. I worked up all my courage, rolled on top of her, silently mouthed the letter ‘H’ … and leaned in. She turned her face away. (Uh-oh.) I tried again. She turned her face again, the other way.
The third time I tried, she kissed me back.3
We had sex a month later, in my parents’ bed, two days before Christmas. We lit candles and ran a hot bath beforehand. It felt like a fairy tale.
Unfortunately, fairy tales never last. After a year of dating, Lucy asked for an ‘open relationship’ — meaning she wanted to see other people. I was scared to lose her entirely, so I agreed. Two weeks later, she changed her mind and we became exclusive again — but not before she’d made out with some guy she’d met at a party. The relationship never recovered.
The magic was gone.
I’m not saying that Lucy was the source of my sexual insecurities — when it came to girls, I’d always felt too small, too skinny, too shy. She’s also not to blame for what I eventually became. But that first relationship left me hurt and confused and I never, ever wanted to feel that way again.
So I started lifting — I put on about 25 pounds of muscle in two years. I acted more confident, more assertive, adopting a bold, cocky persona that often crossed into arrogance — which, for some reason, girls seemed to like!
I managed to attract a few girlfriends in college — usually girls as insecure as I was. We’d latch tightly onto each other and bond deeply before I’d inevitably decide to see other people. Girls said I had ‘commitment issues’. They called me a ‘fuckboy’.
I didn’t want to be a fuckboy. I wanted to Respect Women, as per my feminist upbringing. But I also felt instinctually that a man’s sexual worth was measured by the number of women he’d slept with. So I was conflicted:
On one hand, I wanted an intimate Romance, a singular love like Jim and Pam. On the other, I wanted to consume women Sexually, to experience their bodies like Jeff Winger in Community. These two desires seemed incompatible.
And then, before I could resolve the confusion, disaster struck.
I’ve written before about the pandemic-induced psychosis that dominated my early-mid 20s: I was isolated, paranoid, and disfigured from surgery. During this time, I slept with exactly zero women. Instead, I bought a Fleshlight in the shape of Emily Willis’s vagina,4 which served as my girlfriend for a year.
Well, eventually, I got sick of fucking a rubber tube… and fell in love with a (real) girl who, unfortunately, could not have cared less about me. Bitter and resentful, I decided on my path: I wanted to sleep with as many women as possible.
So I did what every nerdy internet kid does to get girls:
I hit the books.
I started with the basics:
The Game, by Neil Strauss, exposed me to the world of pick up artistry and convinced me that seduction was a learnable skill.
Models, by Mark Manson, mapped a path to becoming more desirable and communicating sexual interest to women.
The Art of Seduction, by Robert Greene, demonstrated the power dynamics of sexual attraction using tangible examples and precise psychological tactics.
I dove deeper into the theory:
Matt Ridley’s and George Miller's works illuminated the evolutionary foundations of sexual attraction. Robert Sapolsky’s behavioral biology lectures described the interplay between genes, hormones, neurons, and sexual behavior. Rollo Tomassi’s controversial blog introduced me to Red Pill theory, which exposed the fundamental inconsistencies in my feminist mental model of intersexual attraction. It turns out, women aren’t exactly turned on by Respect.5
I submerged myself in the lives of Charles Bukowski, Tucker Max, and Giacomo Casanova. I read erotic literature by the likes of Anaïs Nin and Marquis de Sade. I even perused a couple romance novels (Kathleen Woodiwiss) to better understand female fantasy. I downloaded clips of Craig Ferguson’s famous Late Late Night flirts. I scoured online forums like r/seduction and SoSuave, where thousands of men shared their experiences and tips for attracting women. I studied harder than I ever had in school.
I kept this all, of course, under wraps. One time, a girl found out and called me disgusting, manipulative, immoral, etc… yeah, fair. But I’ve come to believe that wanting to sleep with women and learning how to get it is perfectly normal. I just maybe went a little overboard.
Anyway, I took my newfound knowledge and hit the apps. I was bold; I was playful; I took risks. And women responded positively!
I learned when to push, when to pull, when to touch, when to tease, when to brag, when to beg, and when to back off. I learned to communicate my intentions clearly but covertly. I learned how to ask a girl to kiss without asking.6
Then I moved to New York, and the dating got dumb easy. If you’re not aware, there is an insane abundance of college-educated women in NYC; in fact,
(no relation), who writes about the statistics of online dating, calls Manhattan “Valhalla for Single Men”.7
So I went a little nuts: I hooked up on Hinge; I canoodled at the club; I brought back the barista from the corner café. Last summer, I tried dating three girls at once, which blew up catastrophically (but gave me a ton of writing material).
Wasn’t this everything I’d ever wanted? I’ve been with dozens of women over the last few years — beautiful, exciting, intelligent women — yet, what do I have to show for it?
Not much. I’m somewhat more confident, sure, but I often still feel like I’m faking it. I still have plenty of sexual insecurities; I still get scared to talk to girls. Part of me is still that small, shy, skinny little kid from high school — the kid who can’t possibly be happy with someone else… until he’s happy with himself.
And that’s something no woman can fix.
“Then Lyra took one of those little red fruits. With a fast-beating heart, she turned to him and said, ‘Will…’ And she lifted the fruit gently to his mouth. She could see from his eyes that he knew at once what she meant, and that he was too joyful to speak. Her fingers were still at his lips, and he felt them tremble, and he put his own hand up to hold hers there, and then neither of them could look; they were confused; they were brimming with happiness
[…] Then before they knew how it happened, they were clinging together, blindly pressing their faces toward each other. ‘I love you, Will, I love you-’ The word love set his nerves ablaze. All his body thrilled with it, and he answered her in the same words, kissing her hot face over and over again, drinking in with adoration the scent of her body and her warm, honey-fragrant hair and her sweet, moist mouth that tasted of the little red fruit. Around them there was nothing but silence, as if all the world were holding its breath.”
[…] “The Dust pouring down from the stars had found a living home again, and these children-no-longer-children, saturated with love, were the cause of it all”
hi kathy
she told me later she was just nervous too. cue j cole wet dreamz
holy shit i just looked her up and apparently she suffered irreversible brain damage from negligence at her rehab facility and has been in a coma for the past year and a half? a lot of mixed feelings right now
I know this is a sensitive, nuanced topic which deserves its own piece perhaps, I’d like to make it clear here in the footnotes where nobody reads that I’m not advocating against respect for women… just that it’s not the primary determinant of physical or sexual attraction.
(lean in for a kiss then pause, watch her reaction)
considering linking the WBE article where he dates 9 women at once in nyc but nah i’ll let u look that up if u are so inclined
Reading this felt like being on a shitty first date with you. I’m gonna go to the bathroom now (so I can leave without saying goodbye.)
I don’t know what’s worse, the fact that after the first girl turned away twice, you still tried to kiss her a third time; or the fact that when you said you wanted to study women you mostly mentioned male authors that you were reading…..