Chaste & Chastened

The 33-year-old near-virgin

I can count on one hand the number of people I've had sex with, and I can count on two hands the number of times I've actually done it. At 33, the same age Jesus was when he was crucified, I've barely gotten more action in my life than the savior Himself. And you know He probably could have been a player if He wanted.

When people learn this about me, they always ask me why, as if I have an answer I'm withholding. I know there are factors working against me—I can't keep a tidy apartment or workspace, I have an extensive toy collection, I dress like a Gothic redneck, and I'm a huge fan of pro-wrestling. Still, those don't suffice for explanation, as there are plenty of people in the same categories with girlfriends, or even a wife and kids.

Though I was born in West Virginia, I was raised in Ireland before the dawn of the Internet, in a fiercely Catholic culture in which dating didn't seem to exist. I returned to the U.S. at age 14, before anyone in my Irish peer group had coupled up, only to find that by local standards, I was way behind. Not that there were a lot of good romantic prospects at a place called Smoky Mountain High School to begin with. (Trust me, it was what it sounds like.)

Model: Robert Ortiz
John Gilhooley
Model: Robert Ortiz

But college—and California—beckoned. Surely the movies wouldn't lie to me. I knew I could expect crazy free-thinkers, massive wild parties, fellow intellectual travelers and the freedom to be myself without judgment. And then I found myself at USC, where everyone was either high on Jesus or substances considerably less legal. The first girl I was interested in lost all affection for me when I told her I didn't like Rush Limbaugh, nor did I believe that multiculturalism was hurting America. Yes, I know I should've lied.

The second, and one whom I truly fell for, turned me down and went out with my best friend instead. Later, she married my roommate. I saw them not long ago. They seem happy.

I had a band in college, which is supposed to turn a person into a chick magnet. I suppose it might have worked if I actually had any musical ability.

I finally lost my virginity at the tender age of 26, with the aid of a credit card. I was staying in Nevada, had the whole day to myself and figured it was about time. Yes, it was $600. Yeah, she wasn't that hot. Hell, she couldn't even pretend to be interested in me for the full hour and even let me finish the deed myself. But there was some penetration, so it counts. And I still have the actual honest-to-god receipt. Because of what prostitutes will and won't do, I also may be the only person whose first kiss came after losing his virginity. (It was a New Year's party, and she was a stranger who thought I was lying when I said she was the first. Couldn't convince her otherwise.)

As far as spending the night with another person, though, that didn't happen until two years later, when a woman 14 years my senior—whom I met at a party but would never have guessed might be hitting on me—found my online personal ad and contacted me. For about a month, we saw each other, though we never called it dating, and I'm not sure even now if she wants it known that it happened. Then a funny thing occurred: I found that when sex was actually available to me, my mind was freed up to think about other things! It was around this time that I became a blogger.

After that . . . years of Internet-dating hell. There was the she who turned out to be a he—"intergendered" being the P.C. term. There was the one who would make out with me all day long, but refused to be more intimate unless I could guarantee her I was ready for the last relationship of my life. (I know: I should've lied—again.) There was the Armenian girl who, after seven dates, still sat beside me with her legs crossed and arms folded. There was speed-dating, which allowed me to get rejected 30 times in one night instead of just once. (Incidentally, it was hilarious how similar every female speed-dater was, all of them either kindergarten teachers, special-ed teachers, or women's rights attorneys.) And there were many times when I'd meet someone, we'd have nice e-mail and phone conversations and nice dinners, I'd think everything had gone well . . . only to have them tell me days later I was nice, but there just wasn't that "spark."

There was one brief interlude when I was on the set of a movie with a cast almost entirely made up of young women—the female extras would hang out in their nightgowns watching Sex and the City DVDs all day, and when the wrap party came around, they were ready to get wild; even my luck couldn't crap out in the face of those odds. But alas, this was in Canada, on the last day of a shoot, and not a connection feasibly maintained. Since then, I've been a real movie actor . . . and still nothing.

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