Mailbag: I’m A Virgin – Should I Sleep With My Best Guy Friend?


I’m a virgin, and I really just want to have sex. I think about it all the time. I want to do it so badly. I’d like some advice on whether or not I should have sex with my best guy friend.

He and I have known each other for four years. We kissed once, and it was fun. Honestly, I’m young and single and I think now’s the time to do fun things like this. It’s like, I have this body and nobody is seeing it.

Seems simple enough, right? But there’s so much to consider. It scares me a little that once I do it, I’ll never be a virgin again. I don’t know why because there isn’t even anything cool about being a virgin, especially after high school. It sounds bad, but I like the innocence that comes along with being a virgin. People view you as a bit of a baby, and I guess I like being taken care of, reassured, etc.

I’m also worried that I might be rushing into this just to lose my virginity. I know, I just said that I fear losing the title of virgin. But at the same time, everyone else talks about sex and maybe it’s a little weird that I still haven’t had sex!!! How many virgins are left anyways???

First off, let me bust the little myth about virginity: it doesn’t matter. Really. I held on to mine until I was the ripe old age of 19, passing up opportunities that likely would have resulted in perfectly satisfying sex. Instead, I held onto my virginity, thinking that I should wait until it “meant” something, that I should save it for my first love. And what did I get for that experience? A fumbling, bumbling encounter with my first serious boyfriend that wasn’t all that memorable.

I’ve truthfully forgotten the details of the whole thing, and I was sober. And that guy? Well, he’s so far in my rear-view mirror, I struggle to remember what he looks like. So if the issue is you being conflicted about wanting sex, but also holding on to your virginity for the sake of making that first time special, my advice is to go out there, find a guy that knows what the hell he is doing, and really enjoy your first time. That will make it special enough. A word to the wise, thought: don’t let it be when you are super drunk and just taking home a random. As much as it doesn’t need to be a big deal, you also don’t want it to be something you can’t (or don’t want to) remember.

Now, onto the issue of that you fear “losing the title of virgin,” and that “People view you as a bit of a baby, and I guess I like being taken care of, reassured, etc.” Honestly, I doubt that the first really has much to do with the second. We all have a friend in our circle who is the innocent one, the one that we all feel like we have to protect, take care of, etc. Your status as that person in your group isn’t likely to be endangered by you turning in your V-card. So let’s just set that one aside.

Lastly, should you sleep with your best guy friend? I don’t know about that. It’s an age-old question: can you really go back to being friends after sex? I actually wrote about it a year ago and one thing I learned from writing that particular column -– and the comments I got on it — is that there’s no definitive answer to that question.

While for me, it’s a no; for some other people it’s yes. Meaning that there’s no easy answer to if your bestie should be the one you lose the big V to. In my opinion, which I’m assuming you want to know since you wrote to me, it boils down to your answers to a few questions: Are your feelings for him just friendly? Are his for you? How will you feel if having sex screws up your relationship?

Answer the questions, weigh the pros and cons of doing the deed with this dude, and make the decision you think you can live with. To be honest, whichever way you go, the odds are you’ll somehow fuck it up anyway. But that’s what this time in your life is for –- screwing up and learning from it. And if you get laid in the process, that’s all the better, right?

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Jenna Crowley

Jenna used to be known as 2NOTBrokeGirls, but then one of the girls actually went broke, so she's struck out on her own. Jenna spends her free time saving the world, one sorority girl at a time (usually while wearing yoga pants), questioning why she decided to get a doctorate, and documenting her love of all things cheese related. You can ask her anything you want about football, using your boobs to get what you want, and pizza at @JennaLCrowley on Twitter or via email at

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