How Long Should I Wait Before Hooking Up With a Guy I Like? Ask a Pro

Head Pro has never had sex at Olive Garden, but it’s something he’d be willing to explore. Send him your questions about life, love and fuck buddies to He’s also on Instagram at @BetchesHeadPro.

Dear Head Pro,

Things have gotten so messed with my f-buddy/booty call “relationship” and I think you’re the only person left who can knock some sense into me.

I’m a junior in college and I’ve been hooking up with this guy for over a year now, he’s a year older than me and we met at one of his frat parties and have been hooking up every weekend since. The thing is I’ve fallen, hard. We would never text besides late at night and this bothered me I wanted to be able to text him to come over for sex during the day also I mean is that not what a f-buddy is for? Anyways we fought more than we fucked and I ended up telling him that I had feelings for him, hoping it would either become something more or end if he didn’t feel the same he pretty much just disregarded what I said and things continued the same.

I feel stupid because this is hurting me more than anything and this was supposed to be more fun and for some reason I can’t get out of it. We’ve gotten into pretty bad fights because I’ve caught him taking other girls home but we still continue to see each other. Is there any chance this guy even has feelings for me if he keeps sticking around? How do I get over it and move on graciously? Or is there a chance I can turn things around and get him to take me more seriously?


Can’t make up my mind

I’m going to let you in on a little secret: Every guy in a FWB situation automatically assumes that the girl has feelings for him. Like, as guys we figure that if you’re fucking us, you’d date us exclusively if we asked — even if this is often not actually the case. It’s not so much a conscious thing as it is that we’re just as guilty of buying into the cultural notion that girls can’t possibly want sex for sex, and instead tie it to love and affection. It’s not ideal, but it explains why he brushed you off when you expressed your feelings: You were just telling something he thought he already knew.

Unfortunately, the problem here is all you. You started with a futile attempt at a FWB situation, which doesn’t imply exclusivity. Then you expressed your feelings which, despite being a noble thing to you, doesn’t entitle you to exclusive ownership of his cock ‘n balls. I’d get pissy, too, if the girl who only ever messaged me for sex started giving me shit for what I did with my own free time. Nothing about him has changed. The only thing that has changed is you. You’re asking him to comply with terms that he never agreed to in the first place.

You need to get a clue. Sure, he likes you enough that he tolerates your bullshit in the pursuit of sexytimes, but he’s made it very clear (through both words and actions) that he’s not interested in exclusivity, at least not with you. Moving on just takes time, and doing it “graciously” just means deleting his number so you don’t invite him over to fuck the next time you’re drunk at 1 pm on a Tuesday. It’s not any more complicated than that.

Dear Head Pro,

So last year I met a guy at a frat party and we flirted a little but overall I felt like I was more into him than he was into me. Fast forward a year and a half, I see him again and I admit to remembering him and we start talking every now and then at parties. My best guy friend is close with him and he told me this guy “likes me” (whatever that means, I haven’t heard that expression since like 2006), so of course I drunkenly ask him to lunch.

My surprise was that he said yes (and yes, I realize that sounds idiotic since my friend told me he was into me). I saw him out again one time since, and he was extremely shy but once I went up to him he asked if we’re still on for lunch and that he’s glad I asked him. We went back to his frat house and smoked with another dude, and I left without hooking up with him.

Now, you have to realize, I’m extremely damaged. The past year and a half, I’ve been going out 3-4 times a week and sleeping with multiple guys per week and falling for douchebags who constantly prove to me that I need to look elsewhere if I want a relationship. Now that I’m actually gonna date someone before sucking their dick, I’ve forgotten what to do. Like, this guy seems pretty timid so I feel like I’m always gonna need to be the one making a move and since that’s the case, I need to know: what’s an acceptable next date? After how long should I hook up with him? I’m just scared I’ll fuck this up.

Help plz,

Just A Thot Trying To Relationship

Yes, tell me some more about how “extremely damaged” you are because you drink a lot and hookup with boys, aka act like every other college girl on Earth. You should make an Instagram account where you post memes about how pizza is bae and how when you text people “on my way,” you’re really still in bed. Tell me, are you also an ambivert?

Assuming your lunch goes well, I think you’re still better off having him plan the next date, even if you have to kind of engineer it yourself. If not for “tradition’s” sake, then at least the knowledge that this guy really is interested in you and you’re not just browbeating this poor shy dude into buying you lunch twice a week. The day after the lunch, text him something like “I had a great time, where are you taking me this weekend?” (or whenever you’re free, you get the point). This let’s him know that he should take some initiative, but also that you want to see him. Shy dudes need that little push sometimes.

As for when/if you hook up, I really don’t care. But if you’re trying to do things differently for a change, maybe don’t fuck him on the Olive Garden table as soon as the busser clears your lunch dishes. Wait a few dates, and more importantly give yourself a chance to decide if you even WANT to bang him rather than assuming it’s inevitable.

Head Pro has never had sex at Olive Garden, but it’s something he’d be willing to explore. Send him your questions about life, love and fuck buddies to He’s also on Instagram at @BetchesHeadPro. And don’t forget to pre-order The Betches next book with wise insights from The Head Pro here >>


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