Help! I’m a 23 Year Old Virgin. Ask a Pro

Dear Head Pro,

So I'm relatively new to my city, moved in with a girl my age who grew up in the area, and even though we didn't know each other well beforehand, we've really hit it off and have become good friends in the past couple months. She started dating this pro right when we moved in, and they are official gf/bf now.  He seems great, she's happy, awesome.  I've been making other friends in our city besides her (obvi) but I do like to spend time with her, and I'll frequently get invited to go out with her, her boyfriend, and her boyfriend's friends.

The problem is, I hooked up with with one of his friends twice recently, when I was regrettably way too drunk.  I've spent some time with that group since then, and it hasn't been that awkward (after talking to this guy sober, I'm not really interested and the feeling seems mutual), the guys are fun and their girlfriends are all great too.  My roommate thinks it's fine for me to keep hanging out with them, but I wanted your opinion on that, and if it's acceptable to continue doing so, how I should act around these guys? I really don't do the drunk hookup thing anymore so any tips on how to minimize that reputation would be appreciated also.


I seriously hate my college friends for not moving here with me

Dear Maybe if You’re the Only One Who Moved There it’s You, not Them,

How should you act around these guys? Well, considering you managed to see one of them naked not once, but twice, I’d say however you were acting up to that point seemed to do a fine job of endearing you to them. Seriously though, stop making drama where there doesn’t need to be any, as though you’re the first person to have hooked up with someone and then had to see them again in a non-sexual capacity. It happens, and it’s fine. But, since you insist on being all “wahhhh, my life is over,” let’s look at some possible (but unlikely) undesirable scenarios that could pop up:

– This guy gets himself a girlfriend, and she becomes a part of the group. If she for whatever reason learned of your dalliances, she could conceivably make things weird. Some bitches be cray like that.

– You get yourself a boyfriend, and he becomes part of the group. In situations like this, sometimes your former flame will magically develop feelings for you and start acting all jealous and weird. Or, if your boyfriend was to somehow find out, every time he sees the guy he has to try to ignore the “hey bro, how’s my dick taste?” vibe.

That’s really all I can think of, and really the odds of a worst-case situation happening are slim. If these guys are actually your friends (or at least, guys you hang out with who have girlfriends and are otherwise not interested), they aren’t going to run around spreading tales of your boring-sounding trysts throughout the community. If you want to avoid having that be your “reputation,” maybe stop doing that, and you’ll be fine. You didn’t murder anyone’s family, and you aren’t carrying any of their babies. You got shitfaced and fooled around a couple of times with one of them. Don’t make it a thing, and it won’t be a thing.

Incestuous Kisses,

Head Pro

Dear Head Pro,

Help I need your advice. Hello Head Pro. So I'm basically 23 years old and I'm a virgin. I was once really uptight/conservative, thought that my virginity was a prized possession until I realized that was just society holding me back from having fun and enjoying one of the greatest things in life . I've been talking to this guy for like a month now and I want to have sex with him, except he seems/is really experienced and is like 10 years older. I don't want this guy to bail on me if he finds out I'm a virgin. I know this is going to make it seem like I can't like the first guy as much, but I'm also talking to a guy (maybe gay bro) who I've always been thinking about having sex with just so he'll prep me well for this pro. What should I do? Should I just spill that I'm a virgin (we talk about sex a lot and I don't think he's up for training a virgin) and have sex with the maybe gay bro or should I just spill the truth? Help me out. And no I'm not going to pretend like I'm so cool that I don't want your advice because I do. Much love.



Dear You,

First things first, a guy you’ve been “talking to for like a month” and/or a guy you think is possibly gay should not be on your short list of sexual partners, whether it’s your first time or your five hundredth. Yeah you’re probably anxious to just go ahead and get it over with, but if I were 23 and still a vigrin, I’d want some fanfare to celebrate the event. Shit, maybe I’d invite the whole neighborhood over for a surprise party, where the surprise is that I make a grand entrance into my living room, naked and no longer a stranger to the gentle ways of the Amazon Sex Forrest. If you can’t find someone who at least likes you beyond “talking,” that probably has as much to do with why you’re a virgin as your conservative origins, and maybe diving head first into sex isn’t the best idea. And no, society is not “holding you back.” Have you been outside lately? People are fucking. Lots of them. Hell, I hear even animals are doing it now too. Sex is like “The Cupid Shuffle” for 2013.

But whatever, more central to your question, how can you surmise from talks about sex that this guy isn’t up for “training a virgin” if he does not, in fact, know you are a virgin? Speaking of “training a virgin,” let’s clear the air with that. You’re 23. It’s unlikely, then (I hope), that your first partner is going to be a teenage boy, mincing and wringing his hands over the whole thing because he’s not so sure of what he’s doing himself. You’re probably not going to be overcome with irrational, chemical feelings of “love,” because you’re an adult and hopefully your hormones have calmed down with that shit. There’s not a lot of “training” involved. There’s no owner’s manual, it’s just sex. You have a vagina. Dicks go in, and they go out, and again and again until one or both parties are satisfied. That’s really all there is to it, and whenever it finally happens you’re going to go “well fuck, that’s what I was waiting for this whole time?”

Is it going to be the best sex you’ll ever have? I surely hope not, but it will be sex all the same. As for bringing up the fact that you’re a virgin, there’s really no bad time, save for when you’re actually in bed and about to go to pound town. In that case, you probably should have told the guy sooner.

Unspoiled Kisses,

Head Pro


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