Ask Jack: 'I hooked up with a straight guy and now I've got a crush on him - what do I do now?'

Jack of Hearts tackles your teen sex and relationship problems from top to bottom.


Over the next few weeks, 17-year-old Jack Rothman, the fictional gay protagonist of Jack of Hearts (And Other Parts) by L C Rosen, will be answering all your questions about gay sex, relationships, and navigating the tricky world of LGBT teen life.

If you've got a question you'd like answering, email [email protected] (all details will be kept strictly anonymous), and Jack will draw from his, erm, wealth of personal experience (trust us) to offer his advice.

Hi Jack,

Home county, small town queer here with a problem! I go to an all boy schools (fun in porn, less fun in real life) and am the ONLY out gay guy. I was at this party hosted by one of my childhood friends and one of her friends invited some guys from my school, including one really hot guy from - #ClicheAlert - the football team.

Night goes on, cider was drank and I find him alone in my friends bedroom. One things leads to another and we end up doing stuff (everything BUTT…see what I did there, I can totally pun in American) but THEN, we had a really cool chat afterwards and just kinda hung out the rest of the evening. Two weeks on and we still text but I’ve now got a big crush on him. He says he’s not gay but surely giving me head rules that out? I guess he could be bi?

But my question is, what do I do? Should I just leave him alone, or try and just be friends, or somehow get him out of the closest (if he’s even in one to begin with?!).


Straight Chaser


Dear Straight Chaser,

Ah, straight boys. Always there to fuck with your head.  I’m sure you’re not alone in the confusing encounter department, SC, and I’d love to give advice like “stay away from the straights” but the truth is, these things happen. They’ve happened to me many times. And often, it’s a lot of fun! It’s the afterwards when it becomes more complicated. After all, you just un-straightened them, right? Surely their mouth on your mouth or your naughty bits indicates a less-than-strictly-heterosexual demeanor? 

In my experience, though, there’s no hard and fast rule. Sometimes, yes, the straight boy you fooled around with will no longer be straight afterwards. But sometimes it was a passing curiosity, now sated, and sometimes it’s even muddier.

An all-boys school probably adds to that muddiness. A bunch of horny young men? There’s bound to be some flexibility there. And some men, especially British ones from what I’ve heard, are polite. You gave him a blowjob, so he gave you one. I’ve known several men who went to all-boys schools who felt that bro-jobs, as terrible people have taken to calling them, are simply part of the culture, along with circle jerks. A way to “make do” without women present. Although you say women were present at this party. Which makes this situation even more complicated. 

Here’s my suspicion, though, and you won’t like it: he’s used to swapping oral with other straight dudes because of the all-boys school thing. But that doesn’t make him gay. He might just like sex, or perhaps being cooped up with guys for so long means he’s realized it isn’t a big deal dabbling with dudes when you’re horny. Call it heteroflexible, or bisexual hetero-romantic, or whatever you want, but he calls himself straight, and that’s really the roadblock. 

It’s okay to hook up with a straight guy. But having a crush on a straight guy, even one you’ve hooked up with (especially one you’ve hooked up with) is just going to be heartbreak. My read here is that he finds it easy to hook up with guys, because he’s done it before. But with women, he feels like he has to take them out, earn their affections before they’ll get physical with him. That’s the patriarchy in action, and we should all be thankful that we’re removed from that nonsense. The fact that he returned the favor is polite, but I think he just has good manners. I wouldn’t read too much into it.

Now, when you’re back at school, what do you? Well, you can probably get into a situation where you sometimes exchange blowjobs with him. Unless this really was a one-time experiment thing. But do you really want that? I mean, I’d be down for it, but you sound like you have a real crush with the feels and stuff.

I think being used as a sex toy when you want to be cuddled like a boyfriend probably isn’t going to do much for making you feel good about yourself. So, I’d vote for leave him alone.  But let me add one more thing: unless there are only four other boys at this school of yours, there are other queer guys, just waiting to be discovered. Closeted, unsure, scared – but that’s how it is for high school for most of us.

Maybe try to find one of those. There’s a blowjob coming your way done with a real love of the job, not just out of courtesy.

- Jack of Hearts

If you've got a question about sex, relationships, or gay teenage life you'd like answering, email Jack at [email protected]*

Jack is a work of fiction created by L.C. Rosen, with neither of them holding qualifications as a therapist or physician. Therefore, he recommends visiting for further information and guidance.

Jack of Hearts (And Other Parts) will be released on eBook by Penguin on 30 October and in Paperback on 7 February 2019. You can follow author L.C. Rosen on Twitterand pre-order your copy here.