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Hey Dude,
I’m 20 years old and I’ve never had a boyfriend or had a first kiss. Not to toot my horn or anything, but I know I’m not unattractive, I’ve had lots of “things”, flirted a fair amount, and I know the whole texting/facebook/hanging out deal, but for some reason, I’ve never been able to seal the deal.

I’ve been hanging out with lots of guys as of late and I’m pretty sure that a few are interested in being more than friends. I’m excited, but this whole inexperience thing also makes me self concious.

What I want to know is, is it weird to let these guys know I’ve never had a boyfriend? I mean I know that they’re going to find out eventually, but when is a good time to mention this? The same goes for the whole never been kissed thing- should I mention these things before/after/or at all? I don’t want to freak anyone by telling them they were my “first kiss”- should I even mention it?

-Kiss and Tell Read More »

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?

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. Read More »