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Dear Chris,
I’m a 22 years old man (soon to be 23) and I’m a virgin. I’ve dated a couple people, but I’ve never had a relationship that lasted more than 3 months. I’ve done stuff with girls but I have never gone all the way. After high school, I assumed it would happen in college, But I went to a community college, and that really wasn’t the social experience that you seem to get at a university where everyone is living in dorms away from home. I looked into going back to school, but it would have only been for the social aspect and I decided it wasn’t worth the debt. I still haven’t left home, but I’m considering going to live and work at a national park, which I’ve heard can be like college without the college bit.

I guess my question is “do you you think that this a problem?”. I imagine you’ll say no. But you could imagine how insecure it makes me feel. Like there must be something wrong with me. Do you think I would be better off finding a Tinder date and having sex with a girl ASAP, eve if I don’t like her that much (not that I think I could) just to get it out of the way? Or should I wait until it just happens naturally. My gut tells me it’s the ladder, but what if I wait and the years go on and it still doesn’t happen? Let’s just say “the 40 Year Old Virgin” isn’t as funny to me anymore.

I think there are a few reasons it has never happened for me. I’m only 5’4 and that just seem to be a problem for a lot of girls, but those aren’t the girls for me. However I am a singer, songwriter, standup comedian, and filmmaker. So it’s not like I have nothing to offer. I think my biggest problem is that I over think. I used to think that that was the way to go because I never made big mistakes, but now my biggest regret is that I haven’t made more mistakes. All my friends slept with people they probably shouldn’t have or did drugs where it was illegal, etc…you know, teenage shit. but now they’ve all got these mistakes that they’ve learned from, and I don’t. It makes me feel dumb.

Seeing that your the sex guy, I’d really love to hear your take.

I hope you know how much you help people. stay genuine.