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

Head Pro is definitely way too old to go to your prom, which is cool, he totally didn’t want to go anyway because he’s actually going to this really chill college party. It’s gonna be, like, really mature and stuff you wouldn’t like it anyway. Email him your questions at [email protected], and follow him on Twitter and Insta at @betchesheadpro.

Dear Head Pro,

Last Saturday was my senior prom, i went with a decent bro but the hottest guy from another school came to the after party, we made out, drank and had the BEST time, in the middle of our drake induced love he asked me to be his prom date to his school’s prom, these words exactly “you’re really fun, wanna go to prom with me?” I said yes, obvsss

But then the next day we barely spoke and haven’t really communicated much since then, so yesterday I took the plunge and snap chatted him saying “hey so you invited me to prom drunk lol” he said “yeah I did” and then I said “funnn! When is it?” And he said “may 18” Before he showed up to my after party he would snap me often but I havent heard anything else from him, I can’t help but feel like he regrets asking me lololol helppp

Lol, he definitely regrets inviting you. As for why, that’s anyone’s guess. Chances are he had planned on asking someone else, but figured asking the cute drunk girl (fresh off the high of her own prom, no less) to prom would get him into your pants. He wasn’t entirely wrong, but because he’s an idiot teenage boy thinking with his sweaty, idiot teenage penis, he didn’t think very far ahead.

I know it’s borderline impossible for a highschooler to do, but I think you’ve gotta ask him point blank what the deal is. It’s not really the kind of thing you want to leave in limbo, especially if your parents are rich and you can convince them to buy you a new dress on short notice. Besides, going to someone else’s prom whips way more ass than going to your own. Every single boy in the gymnasium is going to spend the entire night thinking unspeakable things about you (much to the chagrin of their dates), just because you’re new. Most people go their whole lives without experiencing that level of petty satisfaction.

So yeah, do the hard thing and get it cleared up. A hot dress, some smooching, and maybe an over-the-pants handy in his car before he drops you off, and you’ll have given that dude a memory he’ll cherish AT LEAST until his first weekend in college.


Dear Head Pro,

So I had a guy I’ve known for years reach out to me on Facebook Monday (after not seeing him or talking to him for close to 5 years) and after some brief chatting, suggested the next time he goes out for me to go too. I agreed but no definite date was set. Fast forward to Tuesday, he messaged me in the evening and said he was out with some of the guys he worked with and asked me to join and after some reluctancy, I did. I had work this morning so I was just having a couple of beers but it turned into great conversation and I had a lot of fun. Well he had been drinking a lot and I didn’t want him drinking and driving so I offered to give him a ride home (he lives 10 minutes from me). He agreed and I took him home and he suggested I just stay the night since it was really late and I agreed.

One thing led to another and we had sex. He still kept chatting with me the whole night about things going on in his life, the death of a close friend, he said about us getting together again this weekend and wanted to cuddle. We stayed up till after 4:00am (I had to be up at 5:30 for work) but I took him to his truck so he didn’t have to find a ride. I pull up to his truck and just went to give him a hug goodbye and he kissed me and said “I fully expect you to be angry with me for keeping you up all night” to which I said “oh don’t worry I’m sure I’ll be texting you to complain about how tired I am. He said he couldn’t wait to hear from me.

I texted him and we did have a brief conversation just saying how much fun we had. I sent the last text and he has not responded. I never said thank you for inviting me out or I want to do it again. I guess I’m a little confused if this is just a routine one night stand or potentially more? Do I actually make it a point to go through the thank you process or bring up the idea of hanging out again or just stay silent till he reaches out again?

One night stand

Christ. One nice thing about getting older is that there’s no one in this universe I’m horny enough for to even think about surviving on 90 minutes of sleep. Selena Gomez and Shay Mitchell could show up at my door with a ball of yarn, a bundt cake pan, and an oil drum full of lube, and it still ain’t happening if it’s after midnight. Sorry babes, I gotta get my 7 and a half hours.

Anyway, in this case I think you’re looking at a standard-issue one-nighter. It’s extremely funny, to me, that you’re entertaining the notion that it’s somehow because you didn’t thank him for the barely-date. Like, I’m pretty sure he took the sex as a more than adequate token of your appreciation. No guy talks to his friends after that and says “we had a nice time, and we totally did sex, but she didn’t send me a thoughtful follow-up text. SO TACKY, right?!?!?!?”

I don’t think he was ever all that into you, given that he put literally zero effort into going out with you in the first place (I missed the part in the play where Romeo gallantly invited Juliet to meet up with his bro pack). But as I often tell people here, it’s unlikely your situation would be made worse by asking for what you want, be it clarification or to hang out again. Probably, he’ll blow you off, but you never know: you could keep meeting up periodically and hooking up, leading to an unbalanced FWB situation that will cause you irreparable emotional trauma. Life is full of delightful little unexplored mysteries like that, you know?

Head Pro is definitely way too old to go to your prom, which is cool, he totally didn’t want to go anyway because he’s actually going to this really chill college party. It’s gonna be, like, really mature and stuff so you wouldn’t like it anyway. Email him your questions at [email protected], and follow him on Twitter and Insta at @betchesheadpro.

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

Head Pro knows better than to even pretend to text you after a one-nighter, because he respects you too much. Email him at [email protected], and follow him on Twitter and Insta at @betchesheadpro.

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 weren’t 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 exclusive hooking up, 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 “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), you have to fucking ask for it. Remember: no guy was ever scared off by the mere suggestion, unless you’re doing it on the first date or something.

Head Pro knows better than to even pretend to text you after a one-nighter, because he respects you too much. Email him at [email protected], and follow him on Twitter and Insta at @betchesheadpro.