Still living with my ex-girlfriend, fresh from the break-up, I first stalkedOkCupid searching for girls based on how quickly I could get sex.

Soon, I had a target. Her picture was non-standard. She was in weird Halloweenesque goblin makeup. Now, I don’t know why someone on OkCupid would do this unless either 1) they were mentally unstable, 2) they had no self-esteem and thus sought safety behind a persona, or 3) they’re a hipster. Whatever her reason, her other pictures were make-up free. When we talked, I learned she was deeply misanthropic. Combining this with her comfort with first-date sex, I was sold.

So, I met her at a bar. She was cute enough, though slightly resembled ET. She spoke in an overly mannish sardonic fashion barely moving her jaw, much in the way an overweight Goth highschool lesbian might speak. Either way, it’s better than the creaky talk/glottal fry of the current female zeitgeist. More troublesome was the foam of saliva perpetually persisting at the corners of her mouth. I forged on. Seduction was my end-game, for after all, she had vagina and she was someone other than my ex-girlfriend.

We spoke and had drinks. My shoddy and self-serving memory retrieves this exchange:

“Are you ‘on’ all the time?”

Embarrassment. Mortification. Being “on” is a common accusation to a comic, which I still was at time. It confirms every comic’s fear: people find you annoying, not funny.

“I’m just trying to be interesting.”

Now this might have been my fault. At the time I was experimenting with illicit drugs which may have changed my behavior into the suspicious. Who knows? I do not yet have the confidence in my career to me any more frank than this, but I’m sure you can figure out what was going on. No, it wasn’t peyote.

• OkCupid Chronicles: No, a Dominatrix Won’t Have Sex With You

I was able to steamroll ahead and finagled her into going back to her place to partake in some illicit drugs, and she agreed. I was golden, right?

Well, apparently, apartment time does not equate sex time. At her apartment, I looked up music on YouTube while she lay in her bed. She offered me nothing and seemed downright annoyed by me. I guess Iwas “on.” At some point I called it a night.

“Well, I guess I should probably leave.”

“Yeah, you should.”

Even now this response pisses me off. She could have rejected my self-invite. Maybe she just wanted to use me for illicit substances. I didn’t know whether to feel like a piece of meat or a rapist. I got home that night and crawled into bed with my ex-girlfriend who was sound asleep. The couch wasn’t comfortable enough and it wasn’t like she could force me out of the bed.

The next first was the first time I would have sex since my relationship with my ex.

A month after that first date, I had moved into a new apartment, and found a girl on OkCupid who was a fellow comedian. She kind of had this Alanis Morrisette / Jillian Michaels / Jew look to her which, based on the pictures on OkCupid, made her seem kind of cute. She was thick like a porterhouse, but not flabby, short and stout like a roller-derby athlete.

I met her at a bar near my apartment and we hit it off immediately. She was a little “thicker” than her photos. But I was still imagining Shawn Johnson beneath her clothes. Besides, she probably had a great personality. I felt more attractive than her, so I didn’t have to worry about being “on” or coming on too strong. I even told her about my first date with the spit-mouth girl.

We drank until I took her back to my place to–you guessed it–engage in illegal substance abuse. (I have never done drugs, okay prospective employers?)  When I made a move, she damn near tackled me. She removed her shirt.

My friend Ray can be the most offensive insulting person in the universe. He admonished me for characterizing her body with such crass misogyny. Thus, this caveat: my evaluation doesn’t come from hate, it comes from sheer surprise, and the urge to be “on.” That said, this is what I told Ray.

“There was… extra skin. Like she used to be morbidly obese but suddenly lost all the weight. Like a Biggest Loser winner. She resembled a Shar-pei or a folded up parachute.”

I hate having to express disdain for someone else’s body. I myself am a little overweight and very body conscious. According to Wii Fit my BMI is 27.55. I’m not saying this girl has no worth. She was a terrific person who deserves love as much as anyone else. Still, she had a shitload of extra skin which I found to be shocking, and frankly, repulsive.

So, I fucked her.

I laid her on the bed and laid myself on top of her and proceeded to get laid as she trembled beneath me, her legs up around my back looking as if she had fallen into a vat of dough. When I ejaculated (spoiler alert), I looked down on her, panting, dripping sweat onto her, and said the first thing that popped into my dumb head.

“You’re the first girl I’ve had sex with since my girlfriend.”

Right. “Girlfriend.” Not “ex-girlfriend.” Not “that was fun.” Not “that sucked.” Not “where did you get all that beautiful skin?” Just the lamest, most pathetic admission of inadequacy I could muster.

I felt like I had cheated on my ex-girlfriend. I had broken our ex-trust–again. I was somewhere between scum and nothing.

I re-robed and asked the girl to come to the stoop with me to have a cigarette. (Besides the illicit substances that I may or may not have been doing with plausible deniability, I had also re-taken up smoking). She smoked too. We talked about my feelings. How I missed my ex, how I was a mess, a shell of a man, a monster, a pseudo-rapist, etc. Of course she was tremendously sympathetic. She assured me she was just casually dating as well and had also just left a long term relationship.

After a few minutes — and by the way, this is why I am a hideous monster — I was able to convince her to leave, not sleep over — kind of a Wham-bam-I-am-an-empty-shell-of-a-hu-man. Maybe I’m not a monster, maybe I’m just a man doing his best to be happy. I made a vow to raise my personal standards, have a higher opinion of myself, not just throw myself at any willing participant. So, never contacted this girl again, except about a month later, on a random night. But I had a valid reason: I was horny.

“Want to hang out?”

“Sure, guy I had a one-night-stand with a month ago. Let’s do that same thing again! You’re a real winner and definitely not a monster.”

In truth, she didn’t return my text. Good for her.

Evan Jacobs is a 31-year-old schlub who used to do stand-up comedy, excel academically and slay the ladies. These days, between the time he spends trying to publish his novel and teaching at a for-profit Manhattan college, he complains incessantly about nearly everything.

Reprinted from Hypervocal