Should I Lose My Virginity to My Ex? [Ask A Dude]

Hey Dude,

I am a girl and I have a male friend, first we were together as a couple but didn’t work out (not anything serious), so we stayed friends. Now, four years after, as friends, we both don’t have a relationship, we hang out a lot and there is something different in the air (I am not very sure). I am a virgin and I want to do something with a guy that I don’t care about “like that”, I want to learn from sex, I want to be good at it, but I don’t want it to be with someone I don’t know (because of potential STD risks). So I thought I could ask him. What do you think? Would it mess up our friendship?

Best Friend Learning Sex

Dear Best Friend Learning Sex,

Great Caesar’s ghost! I applaud your approach. I do. There are a few diverging opinions when it comes to the “right” way to burn your V-card. Some wait for a person they love (see Julie Taylor on “Friday Night Lights”) while others might have given it up in a tuck on a drunken night, (see Becky, Mindy and all of Mindy’s stripper friends on “Friday Night Lights”), and then there’s always the good old fashioned, “lose it on prom night,” (see Kelly and Zach on “Saved By The Bell”-wait, nobody talked about sex or was it implied that anyone in that universe had sex, that it even existed, in fact they were all Barbie and Ken dolls by all accounts-wait, no, I’m thinking of American Pie).

But really, it comes down, I think, to the individual. I mean, some fathers take their sons to a prostitute when they come of age (that age varying on cultural, religious and socioeconomic backgrounds) while others practice abstinence until marriage. And I think that ALL of those scenarios, and the thousands of others, (both in this world and “housed in the middle ground between light and shadow, between science and superstition…an area which we call the Twilight Zone”) are VALID. That’s right, I said it!

When it comes to sex, there are bad scenarios. There are awful ways to approach it. Ways that are regretful, some humiliating, and others criminal. But that’s not at all the kind of exploring of your sexuality that you’re debating over. I think wanting your first time to be with someone you trust is reasonable. You’re unattached but have the urge to lose and to learn then by all means, have at thee! But will it risk the friendship you’ve established with your ex? YES! YES! YES!

You can’t introduce sex into a relationship without rewriting some of the ground rules. Many iconic couples have attempted what you’re contemplating. Jerry and Elaine (and damn they had some impressive ground rules). Robin and Ted (hasn’t ended well so far but I have hopes for Season 9!). The arrangement works for a while until one or both cross some boundaries. And the fact that this arrangement involves you having sex for the first time might add a layer of responsibility. It might not. It might. It might not? It might? I’m on the fence. Ideally, it shouldn’t. Practically, it could.

Can you separate sex from feelings? Sure. Like anything else, the balancing lasts for a while, until you do eventually have to rebalance due to the infinite X factors of life. I believe you’d be fine using this guy as your learning curve. Would he? This becomes a matter of two people agreeing to this situation. And if “something” is different, like you think, then you might want to get a little more grounded about what is different before you bring up the matter.

If it’s meant to happen then you can let it take its course. Seems like the best way. You can confront him about it. It’s always an option but forcing these things hardly ever seems to work. Except in crappy teen movies (that you tend to think are amazing until you’re in college). And even in those there’s a period where things have to go really wrong first.

This one dude’s opinion: weigh the pros and the cons. Yes, you risk the friendship. Yes, you might create a whole new dynamic that might be more satisfying. You can let things take their course, be direct and talk it through, or maybe add some alcohol to the equation as an accelerant (I’m not suggesting that’s the WISEST course of action). However, understand that this will change things fundamentally between the two of you, regardless if it’s for the better or the worse. Ask yourself the question: “am I willing to sacrifice this relationship, as it is, for something I can’t predict?” Because you can’t be certain where the choice will lead you until you make that choice. So prevent yourself from choosing poorly and make sure you’ve got your bases covered. Why now? What is holding you back from sharing this experience with someone else? Is there a timetable you’re feeling? Why him and not another friend? These aren’t all easy questions. The answers may even change between asking them a first and second time. But to take care of yourself you have to ask them. And when you think you’ve got the answers then you’ll feel surer what the best scenario for you is.

“Don’t call me chief!”

The Dude

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