Should I Hookup With My Sleezy Guy Friend? Ask A Pro

Head Pro is happy to answer your questions about friends, fucking, fucking friends, and fucking while the TV show ‘Friends’ plays in the background. Email him at [email protected]

Head pro,

I’m going to get right into my problem. So basically I have been talking to this guy for about a month. I had made out with him at a party a couple weeks ago. Fast forward a few days ago and we’re having a more extreme hookup. He goes down on me (without me asking) and right as I start to return the favor he tells me “this isn’t really going to work because I jacked off a couple of hours ago at home.” Obviously, I was humiliated. He has still talked to me since and I even had dinner with him yesterday, so I don’t think it was because he didn’t like me or something. Is not getting a boner because you just jacked off a real thing?


confused af

Is everyone who reads this site officially too young to have seen There’s Something About Mary? I mean you’re not missing much, but the point is that it’s relatively common for guys to ease some tension before they go out when sexy times might be on the table. It’s a stamina thing — if a guy maybe hasn’t gotten laid in a while, he’s going to be concerned about popping off too quick. To reduce that risk, the natural thing to do is to give yourself a release beforehand.

Sometimes this works swimmingly, and we fuck like sex gods and you’re none the wiser. But other times, it backfires — alcohol is a major culprit in desensitizing our dicks, and of course there are nerves, stress, exhaustion, etc. to be considered. Either way though, there’s no way it’s about you. If he was already ear-deep in your biscuit, at that point there’s very little you could do to put him off. In fact, the masturbation could have been a diversion, and anything else could have been to blame. Personally, while I love a good sloppy knob job, I actually don’t think I can recall one so superlative that it took me to the finish line. But again, that’s on me, not your mom.

It’s normal, you’re fine, carry on.

Dear Head Pro,

After reading your book and taking some ABSOLUTELY QT pink themey pics, I had to email for some serious advice. So… backstory: I don’t hangout with most people but my Go-To’s are Two people, sometimes three. My bff and my other bff whom is a boy and we’ll call him David. Anyways, David is somewhat of a SOB (and a fuckboy so he basically is attracted to anything that has a vagina and two legs) , and at any club he goes to the bathroom and is completely trashy, like… ew, with some really ugly stickfigure girls.

But he’s kind of hot. I really want to hookup with him but still remain friends. We’ve both playfully expressed no interest in eachother (but c’mon let’s be honest) Maybe just a hookup won’t hurt. So, I guess I’m asking how do I hookup with a good guy friend while him remaining a good guy friend?

Well first of all I don’t for a second believe you read our book. Mostly because if you’re friends with someone (the person you want to hook up with, no less) who hooks up with girls in bathrooms, you probably live in a place where meth is the biggest contributor to the GDP and in all likelihood can’t read. But also, because this is a really annoying question that I thought we covered in the book. I don’t know; I’ve legitimately only read the parts I wrote myself.

Let’s break down why this is bad and won’t work. First, you sound like a creepy fucking rapist. “We’ve both playfully expressed no interest in each other (but c’mon let’s be honest).” Whoa there, Brock Turner. Sure, you can absolutely have the kind of repartee where you’re playfully dismissive of each other, but breaking through that is a little more delicate than “I wanna fuck him, so how do I do it?” You don’t know how dismissive he actually is, and you might not like the answer were you to find out for real.

More importantly, and I’ve said this 15 thousand fucking times: he’s not your friend if you want to fuck him, and CERTAINLY not a “good” friend. That’s not what good friends are for. Particularly when it comes to mixed-sex friendships, it’s CRUCIAL that both parties view one another through a lens as sexless as possible in order to provide the proper support. Which brings me to my final point.

You can almost certainly fuck him, and of course you can keep being his “friend,” but there’s very little chance of you doing both. I can count the number of times a couple of “friends” hooked up and went back to the way things were on Jason Pierre Paul’s right hand — sex changes things, and very few people are cavalier enough about sex for it not to. And let’s face it, you’re not one of those people. You’re throwing shade at the women he chooses to hook up with, and you haven’t even hooked up with him yourself — how do you think that’ll go over on the off chance you do?

If you have feelings to your friend, admit it. If you want to find someone attractive to have sex with, well, that’s easy enough. But mixing the two is a very bad idea.

Head Pro is happy to answer your questions about friends, fucking, fucking friends, and fucking while the TV show ‘Friends’ plays in the background. Email him at [email protected]