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Dear Breakup Girl,

I'm a big fan, so I know you can help me. I'm a very attractive, smart, funny, woman in her early 20s. I'm also the oldest living virgin (or at least that's what it seems like). It's not that I'm waiting for anything; I've never been waiting for anything. It's just that the opportunity and desire have never coincided. In fact, there have been times when I wanted to have sex with guys, but they didn't want to. My longest relationship was only six months, and that was on again/off again. And there were times when I felt that a guy would break up with me if I didn't have sex with him which is the perfect reason for a self-respecting girl not to have sex with a guy. Lots of guys ask me out, but I'm very picky, which is why I've only had a handful of real relationships.

Anyway, since I don't want to feel like a total loser, I lie to all of my friends about this. I make up stories about losing my virginity. The problem is that the fact that I'm a virgin makes me incredibly nervous around guys. I'm afraid of being laughed at or rejected if I tell them, and I know that eventually I'm going to have to tell them. I think that may be why I've gone for younger guys in the past.

While none of my relationships have gone well in the past, I've never been broken hearted because I've never dated anyone I was serious about. I've never even referred to anyone as my boyfriend. Well, now I'm dating someone – someone several years older than me. We've only been on a few dates, but I know sex is going to come up at some point, and I'm terrified. I like this guy, and I could see us getting serious. I lie awake at night planning what I'm going to say. I imagine he'll be shocked, that he'll laugh at me, and that I'll be completely embarrassed. Of course, it could go well, but I feel like such a freak that I can't imagine how it could. How do you think I should approach this subject with any future guy?

–Sexless

Dear Sexless,

Oh, punkin, please tell one friend. And please tell me you have at least one friend who will understand why you fudged. I certainly understand why, but your "Oh, it was in the back seat of a car … on a sinking ship!" yarns really serve only to isolate you further.

By the same token, please tell me you would third-date only guys — this new one included — whom you can already tell would never in a million years be such big dumbass losers as to laugh at you if they found out. See, that's why I said in my intro that — while I know this virginity is a huge deal to you — for all practical purposes, at the outset, it's beside the point.

Still, yes, even the coolest guy (non-virgin) might be a teeny bit weirded out. Not because he thinks you're a freak, but because of the status and responsibility might thus perceive himself as having. Eek, I've gotta be great. Eek, I've gotta make it perfect. Eek, this is going to be even more Meaningful for her than I'd anticipated. For a guy who's already genuinely gotten to dig you, Sexless, I think that, if anything, would be the only wrinkle between the sheets.

So how to approach it? Well … not between the sheets. If that's where it comes up, you're perfectly entitled to say No then and there without a complete explanation. Rather, at the next mellow opportunity, you might want to say something like: "I'm not sure what significance this will have for you, and we can talk about that, but I thought you should know that I'm actually a virgin."

(Eeeuw, I'm really getting to hate that loaded word, by the way, but after weighing other possibilities, I've decided that any dorky/fluffy euphemism — "I've never been inimate with anyone, blah blah" — will result in his saying, "I'm sorry, what?" and thus you're saying, "OKAY, OKAY, I'M A VIRGIN, DAMMIT!" and then we're right back where we started.)

(Also, gentlemen? Feel free to weigh in on how you'd like that news delivered. I'm curious.)

Take it, gently and awkwardly, from there. This is heady and complicated and uncomfortable stuff, I know. But as crass as this will sound, it's probably easier to tell him you've been waiting than it is to tell him he's gonna have to.

Love,
Breakup Girl

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