The 27 Year Old Virgin

Forget Hollywood. We found a real-life stand-up comic who nearly reached his fourth decade without getting laid.
-By Dan Naturman
Illustrations by Coulas and Lourdes

I was 24 years old the first time I kissed a girl. That is not a typo. Most guys had their first kiss when they were wide eyed young boys, in the wood-paneled basement of their neighbor’s house, or at summer camp, stealing a moment in the woods behind the arts-and-crafts shack. I, on the other hand, was a law student with chest hair. Rare is the man who can boast a class on the federal tax code and his first kiss on the same day.

The young lady, about the same age as me, was named Sonia. We were set up by a mutual friend. Sonia was attractive and had a really good body. I took her to the restaurant on top of the Beekman Tower hotel, in Midtown Manhattan. It has an absolutely amazing view of the city. I don’t remember what we talked about. I’m sure I asked her about her job and she probably asked me about law school. No doubt I tried to steer the conversation to the topic of stand-up comedy, which was something I had just started doing and believed at the time was a lot sexier than being a law student. I do remember that, as we were leaving, she pointed out a couch in the corner of the lobby and said that it would be a cool place to make out.

Any normal 24-year-old male would have realized that such a statement was a hint, and not a very subtle one. But I was by no means a normal 24-year-old male. Seven years earlier, the day I was shipping off to college, my father had sat me down for “a talk.” The talk, in fact. I was 17 years old, but I looked about 12. Puberty had only just started for me. I was five foot one and scrawny and had a big nose. I still have a big nose, but back then my face was smaller, so it looked even more ridiculous.

My father sat me down and started mumbling about girls, and living in the same dorm with them, and did I have condoms? I was thinking, Does this maniac really think I’m getting laid any time soon? Why is he doing this? Perhaps my mother had put him up to it: “You need to talk to Daniel about safe sex. He’s such a handsome boy, like a young Alan Dershowitz. The girls are going to be all over him.”

I gave my father a simple “Don’t worry about it.” Thankfully, he backed off. We continued packing my Fruit of the Loom tighty-whities and tube socks with the three stripes around the top into the car, and we drove off to the University of Pennsylvania, where, as I had expected, I went without female contact of any kind for the next four years.

So, yeah, I was oblivious to Sonia’s comment about the couch. I thought she meant the couch would be a good place to make out if you happened to be with someone you found attractive.

And yet, as we walked along Central Park West after having dessert in a nearby café, I asked if she would like to come to my apartment to watch TV. To my amazement, she accepted.

Sitting on my couch, Budweiser in hand, while watching Letterman, Sonia asked about a VHS tape resting on top of my television. It was a porno, and it belonged to my roommate. I hesitated a second, then simply told her the truth. She asked if we could watch it. I certainly was not expecting such a request, but being the good host that I am, I popped it in the VCR.

We were now watching a girl get bent over and stuffed like a Thanksgiving turkey, and I was still
wondering if I should make a move or not. I actually thought there was a reasonable chance she might push me away in disgust. I imagined her screaming, Can’t a girl hang out with a guy and watch porn without being sexually harassed?

But I finally convinced myself that this was as clear a green light as I was going to get, and I went for it. I planted my lips on hers and, wouldn’t you know it, she didn’t push me away at all.

We were kissing! I just kind of followed her lead, her tongue playing Fred to my Ginger. After a couple of seconds she asked me if I always kept my eyes open when I kissed. All I knew about kissing I had learned from watching other people, mostly in the movies and on television. Were Bogie’s eyes closed when he kissed Bacall? They must have been. I mumbled something in response and resumed kissing her—eyes closed. Whether or not she suspected that I had never done this before, I don’t know, but who would suspect a 24-year-old with no obvious psychiatric pathologies of never having kissed a girl?

At this point I felt sufficiently confident to unbutton her shirt and pull down her bra. After spending some time licking her small but nicely shaped boobs, I moved the operation into my bedroom. Things continued to heat up, and she said she wanted to have sex but couldn’t, because we barely knew each other.

A few moments after that, she came out with a curve ball: “You’re not gonna rape me, are you?” She was obviously into some kinky domination shit, but of course I didn’t pick up on this at the time and simply said, “No, of course not.” It was as if she’d said, “I’ve been a really bad girl—I need to be punished,” and I had responded, “Don’t be so hard on yourself.”

I was an idiot, failing to pick up on any of the brick-heavy hints she was dropping, and the passion eventually petered out.

That’s right, I failed to close the deal. But don’t forget: This was my first kiss.

Well, you must be wondering, If his first kiss was at 24, when did he have sex for the first time? Full disclosure: I’d actually popped my cherry two years earlier at an Asian massage parlor, but that doesn’t really count, does it? (And there was no kissing allowed.) The first time I had sex with an actual unpaid civilian would not be until three years later, at the embarrassing age of 27.

There, I said it. Sure, there were some near misses in between Sonia and My Big Night—a broken futon couch and a surprise S&M enthusiast, to name just two—but circumstances conspired against me every time, and it didn’t happen for three years.

The deed finally went down one magical fall night when I put the lessons I learned from Sonia to devastating use.

I was performing at the Comic Strip, a comedy club on Manhattan’s Upper East Side. It opened in 1976 and is the place where Jerry Seinfeld, Chris Rock, and Eddie Murphy got their starts. It is also where hundreds of comedians you’ve never heard of got their starts—many of whom are, at this moment, cooking a can of beans on a Coleman stove in a rooming house, their dreams of stardom replaced with thoughts of causing harm to themselves and others. But I digress….

I was a young comic, and happy to be getting paid to perform in New York City—although at $15 per weeknight, it was very close to volunteer work. After getting off stage, I sidled over to the bar where my friend Tom, another comic, was having a drink with two girls, Sally and Lisa. I vaguely knew Sally from seeing her at the club a couple of times before. She had a pretty face, but was rather heavyset—plus-size, if you will—and I was not particularly attracted to her. Her friend Lisa, on the other hand, was a total cutie. Naturally, Tom was going for her.