Pillow Talk with Diana: “Should I Tell Him I’m a Virgin?”

Q: I’m a 23-year-old single girl. The other week, I met a great guy, and we had an amazing first date. We’ve been talking on the phone and via text since then since we’re both away for the holidays, but we’re planning on getting together when we get back into town. He’s smart, really sweet, and I’m really attracted to him. There’s just one problem…I’m having a lot of anxiety about my first time. I’m a virgin. I feel like it’s going to be so obvious to him if I don’t tell him beforehand, but if I do, he might be freaked out and have second thoughts about sleeping with me. What should I do?

By Diana

A: Although I’m not exactly of the mind that your first time is/has to be the candlelit, looking-into-his-eyes, two-souls-connecting kind of sex, I do firmly believe you’ll both be better off if he knows that it is indeed your first time. And not just because it’s the “right” thing to do, although I do feel like he has the right to know, if only because that kind of lie is a rocky foundation on which to build a relationship (if that’s what you want to do).

But besides that, think about yourself! Sometimes, when two people sleep together for the first time, it’s hesitant, sweet, get-to-know-you sex. Sometimes it’s not and you’re up against the wall and swinging from the ceiling fan. Believe me, it would benefit you that your first time isn’t the latter. Yes, he should be sensitive to your needs anyway, whether or not you’re a virgin, but a little extra TLC wouldn’t hurt for your first time around–and he can’t necessarily provide that if he has no idea.

That said, if you’re sure you’re ready to have sex and sure that you’re ready to have sex with him, then there’s no need to making a huge, dramatic event out of telling him. Pick a good time–not while you’re hooking up, and definitely not right as you’re about to have sex–and then take your advice from Nike and Just Do It. The more casual and at-ease you appear about it when you tell him, the more likely he is to not make a big deal out of it. I would wait until the hooking up has gotten hot and heavy, and then at some point that night, just say something like “by the way, and I don’t want this to freak you out, but I’m a virgin. I don’t have any complexes about it or anything, but I just wanted you to be aware of it if we sleep together.”

Approached the right way, I think you might be surprised at how understanding he is. Use protection, and have fun!

Got a question for Pillow Talk? Email it to pillow.talk.cc@gmail.com and we’ll tackle it next time!

[Photo via Dear Sugar]