It's A Pleasure

Is It A Bad Idea To Lose My Virginity To An Old Crush?

I want to get my first time over with, but I don’t fully trust him.

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Q: I’ve had a crush on my guy friend on and off since I was 13. It went away in college as he lived his frat boy life and I realized I’d been carrying the friendship more than he had been for the last few years. I couldn’t see us in a relationship together anyway. We’ve stayed in touch and have been talking more since I moved to a new city a few months ago. Historically, I’ve been quick to give my power away to him, but I’ve grown enough to change that. I’ve never had more self-confidence.

Recently, I visited home and we met up on a night out. I found myself shocked at how easy, fun, and familiar it was to be around him. The last time we were truly close was almost 10 years ago, but it felt like no time had passed. There were definitely vibes from him, which led us to talking about me coming home with him. It didn’t end up happening, which I’m fine with. We were both drunk, and I got the validation that there is definitely chemistry there, which was more than enough for me. The following day, we acknowledged what (almost) happened over texts and joked about it.

My question is: Next time I’m home, do I bother hooking up with him, or do I save myself from the potential mind-f*ck and keep that can of worms closed? I’ve never been with anyone before, and I’m at the point where I want to get it over with, but not to the point where I’ll just do it with a stranger. It’s something I’m self-conscious about but I know I would feel comfortable and physically safe with my friend. I don’t want anything serious from him and believe he feels the same. Aside from the fact that I don’t emotionally trust him, we live in different cities and I’m not about to have my first relationship be long-distance.

My concern is if it’s a bad idea to go there, given our history. I feel like a lot has changed since I was last hung up on him, but I’m nervous that going there would throw me back to where I was in college — hurt and confused and way more into him than he is into me.

A: Let me start this letter with the gentle and loving reminder that virginity is fake. We made it up, like Santa, to go hand in hand with religion and guide young people to behave in certain ways. As a concept, virginity is heteronormative and harmful and limiting. However, just because virginity is a social construct doesn’t mean the emotions around it are fake.

Feelings about sexual milestones are entirely real and often consuming, but first-time sex doesn't have to go a certain way or be with a certain partner. It doesn’t have to be special or romantic. You don’t have to wait to find the right person. You can just decide you want to hook up with someone on the spot and then do it. If you’re into it, that’s enough! You don’t need to strategize about how to make the situation go as smoothly as possible, although I understand the inclination to. The truth of the matter is that sex is often unpredictable and messy — both emotionally and literally. But it can also simply be a fun thing adults do together like playing tennis or Super Smash Bros.

I’m not saying you’re overthinking the decision. It’s more that I want to give you full permission — not that you need it from me — to mess it up, to pick someone who ends up not being great. All you can do is try your best to do what feels right in the moment. The outcome might not be exactly what you thought it would be, but that doesn’t mean it was a terrible decision. And even if you do somehow make a certifiable Bad Choice, that’s OK! Please join the club of people who made iffy decisions on whom to bang the first time. You’ll find, like, 76% of the population is with you.

The closer you get to people, the more likely you are to get hurt.

However, the question I really think you’re asking is this: If you hook up with him, will you get hurt? And the answer is maybe. Actually, the answer is probably. But that doesn’t make it a bad idea. This next sentence is going to sound like the voiceover at the end of an episode of a CW teen drama from 2008 but it’s just true: The closer you get to people, the more likely you are to get hurt. You already have a history with this friend, and you’re considering getting even more intimate.

Now, maybe you’re an easy, breezy, emotionally unaffected person, and sex won’t change much of anything. That is absolutely possible. But ultimately, none of us has any idea how anything is going to go. We cannot outthink life. This isn’t a screed against being careful or measured when making potentially emotional decisions. I just urge you to remember that no matter what you do, there’s the chance for both pain and pleasure.

So, is this guy the right guy to do this with? My inclination is that he’s probably a mostly OK choice who comes with some great benefits (you feel safe with him, you’re both into each other sexually). But — are you listening, America? — history cannot be ignored. This is a person you’ve liked on and off for years. That attraction could lead to hotter sex, but it could also lead to a dicier fallout. That’s especially true because of the dynamic you describe between the two of you.

You use the word “power” and that you don’t trust him emotionally. I’m so, so happy you’ve noticed the patterns that you both perpetuate — that you feel like he both has more say in and puts less effort into the relationship than you do. It’s a common, if unintentional, behavior that many cis men engage in: appearing to not care in order to seem impressive/hot, then acting disdainful toward any emotions that crop up as a result of their actions. They were socialized that way, and it sucks for everyone. (Women are generally socialized to meet men where they are emotionally, to mirror their vibe; the inverse happens less often.) I suspect — and maybe I’m wrong — that if you hook up with him, afterward you’ll both be locked into a heated battle to win the useless title of Who Can Care Less. This means that when you feel an emotion — any emotion — after hooking up with him, you might feel like you’ve failed. Like you’re losing.

At some point in life we all (hopefully) learn that the person who “wins” isn’t the person who held back more. No one is meant to feel nothing. When you go to lunch with a friend and have a great talk, you leave feeling something. When you have a nerve-wracking meeting with your boss, you feel something. That’s how it’s supposed to be. So if you do decide to hook up with him, do not enter into the contest with him. Do not try to feel less. Experiencing emotions doesn’t mean that you’re asking for a relationship or that you’ve fallen desperately in love. It means you’re human. I don’t want you to lose an ounce of the confidence you’ve gained because you feel something — even a little, tiny, spark — for someone after you had their junk in your mouth.

And! If somehow, everything goes exactly opposite to how you planned it and you do hook up with him, and you do get hung up on him for a while afterward, and it does hurt like hell, and your confidence is dinged for a bit, that’s normal, too. That happens to us all. This doesn’t have to go smoothly for it to have been worth it. It can be a lesson; it can be an indulgence; it can be a good story; it can be a mistake; it can be absolutely nothing at all to you. It’s all OK. That’s sex and dating, baby! You have all the tools you need to bounce back after a crush on this or any other guy. You’ve done it before and you can do it again.

It’s A Pleasure appears here every other Thursday. If you have a sex, dating, or relationship question, email Sophia at or fill out this form.

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