My Hookup Can’t Keep It Up—Help! Ask A Pro

Having a penis doesn’t make Head Pro an expert on them, but he’ll do his best. Email him at, and follow him on Instagram and twitter (lol, twitter) at @betchesheadpro. For more of the Head Pro’s advice, buy our new book.

Dear Head Pro,

I just want to start off by saying that I love your column (completely irrelevant, but I’m a huge fan). Anyway, here’s my story: I don’t normally use Tinder, but the other night I couldn’t sleep and found myself scrolling through Tinder for some late night entertainment. I came across this guy that I’ve talked to a couple times at parties and who I mutually follow on Twitter and Instagram. I decided to swipe right, thinking nothing would come of it but also hoping something would. Immediately I am told that he also swiped right/we matched/we all know how Tinder works. Yay! It was around 2am and I decided to wait until later to message him/wait for him to message me. When I woke up later, I started worrying that I shouldn’t have swiped right. It’s been two days and there’s still no message. Should I have just messaged him and went for it, or does no message confirm what I didn’t want to happen-that he just swiped right because we both know each other and to be friendly? I don’t want to sound crazy but I’ve been thinking about it a lot. Please send help!

I don’t know how to use Tinder

Hey now, unsolicited praise is ALWAYS relevant. I think this is a classic case of overthinking things. Like, how on Earth is a tautologically positive result something you’ve managed to twist into a bad thing? Not messaging him at 2am right after matching was definitely the right move (I can’t imagine a way to look thirstier), and my guess is that since he’s already met you in person and sees you often enough (both on the web and IRL), he didn’t feel the need to message you via the app.

I’ll confess I’m not a huge Tinder user, but as I understand it, you had no way of knowing you popped up in his feed, right? As in, he’d have no reason to swipe right “just to be nice,” because he could have swiped left and you’d have never known, right? Since you were notified immediately, my guess is that you popped up in his feed first, and he right-swiped you first.

This is a win-win for both of you. He established some interest, and you went ahead and confirmed mutual interest for him. This means nothing by itself, obviously, but at least it’s a topic of conversation for the next time you’re both at a fun party and want to make things awkward AF.

Dear Head Pro

What is the best way to react when a guy loses his boner in the middle of sex? Assuming it’s not alcohol induced. I’m seeing this guy and he doesn’t like to have sex, everything else is good and he’s excellent at all the other physical stuff but he’s reluctant to have run of the mill p in v sex and I don’t know why. Any time we have had sex (and those times are far and few between) he looses it and gets embarrassed and I’m struggling to understand what I need to do so he knows it’s not a big deal. I feel like it’s coming from a self-esteem issue but in any other situation he’s outgoing and confident. Help.

Is it me?

Fuck, that would be terrible. I think in all cases, regardless of the potential cause for the deflation, your best move is to be warm, supportive and light-hearted. That’s true even if you’re just trying to get your fuck on with some guy you couldn’t care less about—you’re obviously mad that you’re not getting laid, but keep in mind that he isn’t either, and going out of your way to emasculate a guy rarely ends well. A kiss and a sincere “it happens, it’s not the end of the world” will go a long way.

As far as this particular guy, I’m neither a doctor nor a psychiatrist, so it’s not my place to say why his dick is dysfunctional (other than that he clearly has some issues). I will say, however, that barring the chance that they’ve decided to make She’s All That into a morbid reality show with you as the central character, I doubt it has anything to do with you. A guy with dick issues isn’t going to go out of his way to try to fuck someone who repulses him. Besides, you all look the same in the dark.

So my advice would be to obviously remain supportive in the moment, and reinforce that you’re appreciative of his continued attempts. After that, have a conversation. Ask a few questions (has this always been a problem?), but mostly let him talk. Embarrassment is a powerful emotion, and just knowing that you’re not put off or insulted by his issues MAY help him overcome them. But beyond that, he may need to accept the idea of seeking professional help.


Hey Head Pro,

I met this guy at a bar and we went on a date followed by a steamy makeout sesh. Verdict was that he was super hot but kind of boring. I decided to entertain a second date anyways because I was so attracted to him and considering him as a sex friend, so I stayed flirty in my texts. Basically the same situation happened this second time around, no true spark but sexual tension. During our hookup we drunkenly discussed us boning the next time we see each other, which I was pretty down for. But this week we’ve been texting and I decided I’m just not into his humor and personality that much. So I’m like ehh, I’m turned off. What is the best way to blow him off? I have acted really interested so I don’t want to be too harsh and like ghost him. Should I just say I’m busy every time he wants to hang out until he gets the picture? Or should I.. God forbid… Tell him straight up? In a man’s perspective, what is the most appropriate way you would Iike to get rejected?

Bored but not desperate

Yeah, I feel you. This is pretty hard because you’ve gone on two dates, gotten physical and you told him to his face that you wanted to fuck him the next time you saw him. NOT SUBTLE. Ghosting would be awfully rude, as you said, but so would an abrupt “sorry, not interested.” That would probably cause him to grow out a beard and start calling women BITCHES and WHORES whenever they don’t respond well to his use of “m’lady.” And while you can’t actually be held responsible for that, the world would be a better place if we all did our part to rid it of people like that.

As a guy, a combination approach would probably be best. As in, be evasive for a while, and then more direct if he doesn’t take the hint. What you need to create here is time and space, because right now he’s probably still sporting wood thinking about all the sloppy blowjobs you promised him. So brush him off for a couple of weeks, and as time passes he’ll a) get the hint and b) forget you exist, such that the most you hear from him is a random text once a month or so when he’s really shitfaced.

If that doesn’t happen, and in particular if his textual advances remain really sincere and enthusiastic, then you’ll have to be more direct. Be equally as sincere—say that you want different things, that he’s nice but the spark wasn’t there—but be firm enough that he gets the idea. The worst thing you can offer a man is hope.

Having a penis doesn’t make Head Pro an expert on them, but he’ll do his best. Email him at, and follow him on Instagram and twitter (lol, twitter) at @betchesheadpro. For more of the Head Pro’s advice, buy our new book.


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