How Do I Date When I’m a 27-Year-Old Virgin?

Dear E. Jean: I’ve never been kissed, gone on a date, or had a boyfriend. At first I told myself that while I was in school I shouldn’t have a boyfriend to distract me from my studies, but I’m now 27 and I still have no man! I fear I’ll die a virgin. I’m just not confident around men. The ones who I think are hot are way out of my league, and the ones who are my friends, well, they don’t see me as anything but. What am I doing wrong? I’m not a supermodel; actually, I’m a bit chunky. I depend on my wit and intelligence (sometimes I think I might come off as too smart or snooty), but I don’t want to dumb myself down to meet a guy. Last year, I promised myself I’d have a boyfriend by this time, and I don’t even have any prospects!—Frustrated Virgin

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Come, come, my snow orchid: I hesitate to give you instructions because I don’t want all 27-year-old virgins going crazy, looting La Perla, and having sex in the streets in a panic over losing their delightful maidenheads. But here’s the plan:

If you send me evidence that you’ve met 27 chaps in the next 27 days—and by evidence I mean you must email me a photo of you with the guy along with a PDF of the following statement completed by each fellow: “I, [here he signs his name], met [here he must know your name to write it down] on [date], and I’m totally [circle one]: Captivated, Awestruck, Mildly Intrigued, Weirdly Attracted enough to give her my number”—then I will pay for a romantic dinner for you and the suitor you like best of the 27.

The fact is, you’re simply not meeting enough men. You need a friendly push. And going up to a handsome stranger and telling him that some lunatic advice columnist may pay for dinner if he signs a statement and poses for a picture will cause you to forget whether you’re being “too smart.” And when you forget yourself, your innate man-slaying instincts will take over. (And, yes, I know asking him to circle how much he likes you is school yard, but the most serious flirting in the world is school yard.) The more men you meet at rugby matches, skeet shoots, driving ranges, cigar bars, dating apps, coffee dates, and charity projects, the better the odds you’ll meet a guy you like. And when you meet a guy you like, it’s only a matter of time before your heart’s set fluttering and you’re laughing, touching, and losing your virginity in the shuffle.

This letter is from the E. Jean archive.

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