How Do I Turn A One-Night Stand Into Something More? Ask A Pro

Dear Head Pro,

The night before Thanksgiving my girlfriends from high school and I went out to this local bar in our town. While we were out we ran into a group of ~older~ boys we all had crushes on back in the day. Fast forward to we’re all drunk and I go home with one of the guys.

This guy and I had a great time, talking and hooking up literally all night. I felt like we had a really great connection and even though it was a one-night stand I’d love to see him again. The next morning I had to rush home so I didn’t say goodbye or get his number. He added me on Instagram that day and I sent him a DM a few days later (on Monday). I asked him to get drinks the upcoming weekend and gave him my number to text me. He replied to the DM and said he had a great time and that we’d definitely get drinks “soon.” He sent a few more messages and seemed pretty into the idea of getting together but didn’t make a definitive plan.

Here’s my question: he didn’t actually text me, even though I gave him my number, he just responded to the DM. He was also super vague about actually making a plan to meet up again and I’m basically just waiting for the weekend to see if he texts me. Is he not into it? Did I text too early and he doesn’t want to plan something that much in advance? I felt like he was down and don’t really see a reason why he wouldn’t want to get together again, unless I did something massively embarrassing that I don’t remember. I guess I just want to know if you think this is something I should pursue or move on to the next one? I wish he would communicate more instead of making vague promises to hang out, I feel so silly but I really can’t tell what he’s thinking. Thoughts, please?



I mean, not to put too fine a point on it, but if there are two things I wouldn’t invest money in, they’re 1) Bitcoin and 2) one night stands blossoming into something more. Like, that’s kind of a beauty of a one-hitter—you got to go the most fun part of a relationship (the sex) with literally none of the attendant bullshit of a relationship. For most people these are rare and beautiful occurrences, and should be celebrated rather than shamed. I mean, you’re out on the biggest shitshow night of the year, you’re talking to a guy you barely know, and then go home and fuck with a combined BAC that could kill livestock. It’s not exactly a recipe for future romance. That’s not to say that stranger things haven’t happened, but people in 17th century Netherlands thought tulips were a pretty sure thing, you know?

There’s not a lot to second guess here, which is good! This guy never had any intention of pursuing this further, and not actually using your phone number to contact you is all the proof you need. Asking why is pointless, because it could be anything. Maybe he has a girlfriend, or maybe he’s really just not that into you—I mean he couldn’t possibly be, because he doesn’t know you. Sometimes a kiss is just a kiss, and sometimes a sloppy, one-night bang-sesh with a quasi-stranger is just that. Cherish it. It’s fun!

Hey Head Pro,

Dealing with a crisis here. I’ve been hooking up with this dude for the last four and a half-ish months. Super casual, and honestly has been the BSOML (best sex of my life). At first, I low-key hated this guy. Not kidding here, I thought his personality sucked, he was annoying AF, and not that smart. Once we got in the bedroom, though, I realized that I could put up with who he was as a person for the sake of a really great lay. 

Fast forward to last week, when we made a move from hooking up exclusively between the hours of 12 and 5am after nights out drinking to spending a few hours together on a Sunday afternoon engaging in deep and meaningful conversation and then getting it on, but in less of a “f*cking” way and more of a “making love” way. I wasn’t sure if I was the only one who was slapped in the face with feels, but I couldn’t get him off my mind for the days following—and this was a completely new feeling for me. All along, I had been dating and hooking up with other people here and there and never thinking of this bro as a guy I would want to commit to in any way. While I knew from a mutual friend that he isn’t really the “girlfriend” type and I’m not really trying to get into a relationship either (disclaimer, we are both seniors in college and getting ready to move to new cities in approximately 4 months), I figured if I felt some way about him I should act on it. I proposed hooking up exclusively—my thought was that it made things a little less casual than they were, we still would get to bone all the time, and it opened the opportunity for things to gradually and potentially become something a bit more. 

I shouldn’t have been surprised when he said he didn’t want to be exclusive, but I was definitely super bummed out. Now I feel like I compromised continuing to hookup with him because of my little proposal. Regardless of the feelings that can easily be shoved aside, I don’t want to stop hooking up because we have serious physical chemistry. 


Sigh. The first thing you should do is stop trying to save time and space by using initialisms, only to turn around and write them out anyway. Two, probably you should stop getting into bed with guys you think have sucky personalities, are annoying af, and aren’t that smart. That’s just good life advice. Like, how did this come about, really? “Wow, I actually hate you in a deeply sincere way, but best to leave no stone unturned, I guess…”?

Anyway, even though I feel like I’ve said this a million times, color me shocked that the guy you liked enough to keep fucking turned into someone you liked when you  fucking, too. Wow, like, wow! Funny how that works. I love it when people are like “omg this is the first time I’ve ever had feelings for someone!!” Like, how the fuck is that possible? How did you make it to college, and through all the bullshit, hormonal, adolescent years that came before it without ever feeling affection for another person? I mean I’m glad you’ve discovered this basic element of human biochemistry, but goddamn this anti-vaxx bullshit is clearly ruining our nation’s youth, and not just because they’re all dying of rubella.

To get to your problem, you didn’t fuck up by proposing exclusivity, per se. You fucked up by proposing , which is both a) not really a thing and b) obviously not really what you wanted. You want something resembling an exclusive relationship, even if it’s [wanking motion] “label-free.” But you didn’t say that, and guys are idiots who take everything at face value (especially this one, remember)—there is no reason on earth for him to take that deal, for the reasons you described above. It’s all of the restrictions of a relationship, but with none of the companionship and actual GOOD shit that comes with keeping the strings attached.

The good news? This probably isn’t going to stop him from wanting to fuck you. I mean, all the components are still there. But in the future, if you want something (like the exploration of a relationship), . Remember: no guy was ever scared off by the mere suggestion, unless you’re doing it on the first date or something.

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