Ask Jack: 'The guy I'm hooking up with wants us to stop using condoms - what should I do?'

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 questionsabout 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.

Dear Jack,

I’m hooking up with this guy and it’s nothing serious but he keeps wanting to do it without using a condom. To be honest, I’ve always found the idea pretty hot but I’m not sure. He says he’s been tested recently and we’re quite young to have anything. Do you think it’s okay to give it try?

-Is Condom-Free the Way To Be?

Oh honey,

No. Look, I’m all about the hooking up and it not being anything serious, but as someone who does quite a lot of that, let me tell you, when it’s nothing serious, it’s usually nothing serious.

And if he’s pulling the bareback fantasy on you, he’s probably pulling it on one of those other nothings, too. And it’s great having a lot of guys you hook up with. But when the condoms come off, a lot of rules need to go into place, and one of those is some kind of monogamy.

It can be more than just the two of you – a network of sexual partners. But unless you can assure that each and everyone one of them is clean and only going unprotected with other STD-free people, this is a bad idea. And doing that would probably require some sort of insane corkboard with photos and thumbtacks and string just to map who’s fucking who. 

Can you imagine hunting them all down and finding out when their last STI test was?  That’s a lot of work. 

Now, I’m not saying no barebacking ever. If that sounds super hot to you, that’s a fantasy that can be fulfilled – very carefully. It means getting tested together and showing each other the results. It means trusting him enough not to screw anyone else bareback. It means something quite serious. So maybe one day, but not with this guy, not right now. 

And no one is too young to have something. That’s… a new idea to me. It’s not like the more guys you fuck the higher your chance of getting something. It’s not cum-ulative (see what I did there?).  All it takes is one screw up – and sometimes not even sexual ones. 

I once had a guy accuse me of giving him crabs, which I definitely did not. Turned out he got it from sharing a towel with his sister. How’s that for an awkward conversation? 

So wrap it up until you’re with someone you can lay down some serious rules with, and expect them to be followed. Otherwise, have lots of protected fun.

-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 Twitter and pre-order your copy here.