Ask Jack: 'As a gay teen who's yet to have sex, what counts as losing your virginity?'

17-year-old Jack of Hearts tackles your gay 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.

First up, Noah Grimes (who you may know from Noah Can't Even by James S. Green) has a burning question for our new teen sex and advice columnist... 

Dear Jack,

As a shy British teenager who can’t even say S-E-X but has to call it ‘bow chicka wah wah’, what do you think I could learn from you? Also, can you pre-warn me what subjects you might tackle, in case I need to prepare a cold flannel? Um… someone, not me, was wondering if you are gay, how much do you have to do before you’re definitely not a virgin anymore?

-Noah Grimes

Dear Noah,

Well, I don’t know if there’s a huge difference between shy British teenagers and shy American teenagers, but if you’re hoping that by reading my column you’ll go from not being able to say sex to having a grindr profile with photos modeled after Olly Alexander’s Paper photospread… well, probably not.

I’m just a seventeen-year-old American boy after all, not a god, but I do hope reading my column will make you more comfortable not just with saying sex, but with wanting it. And those are the topics I’m most curious about.

What turns you on but you’re afraid to say out loud? Besides the word sex.

In fact, since I practically know you from your stories, maybe we can skip over teaching you to say ‘sex’ and go right to your saying ‘fuck.’ We can practice together when I’m over there in the fall. Sound fun, Noah?

But as to your big question: Virginity. Virginity is such a straight person concept, isn’t it? ‘Ah yes, now that my penis has gone into your vagina and caused bleeding, we have proof that you were heretofore (I’m trying to sound more British here) a virgin, and so an undamaged item, and now I own you and don’t have to return you to your father,’ or however it worked. The fact that it’s still an idea is sort of ridiculous.

Like, why do we care? I can get you may want to tell someone if you’ve never done something before if you’re about to do it, but there’s a wide range of naughty things we can do for the first time beyond trying to make a hymen break. Especially when neither of us has a hymen.

This is sort of one of the joys of being queer, I think. We get to redefine everything.

So I think when it comes to virginity, the best way to redefine it isn’t as a switch that’s been turned on, or a cherry that’s been popped, but more as a wishlist:

-gotten jerked off
-jerked someone off
-given a blowjob
-gotten a blowjob
-played with a sex toy
-been blindfolded while someone went down on me

Etc. so on and so forth. For me, the first thing on my list was having someone else jerking me off. When it happened, in my mind, I was no longer a virgin. I was jerking him off at the same time, to, but that seemed like the second thing on the list. Your list might be totally different, though!

The great thing about thinking of it as a list is it becomes less about ‘what you’ve done’ as some sort of proof of something – your hymen being intact enough, so that now your husband can continue to stay married to you and own you, for example – and more about what you want to do.

And the emphasis there is on WANT. Things you’ve fantasized about, or that you’re curious about. Not stuff other people or society or terrible teen movies tell you should be in to.

So I’d recommend making that list. Maybe you’re not a ‘given head’ virgin, but you’re still a ‘getting it in the ass’ virgin. And maybe you don’t want it in the ass - that’s cool too, and never doing it doesn’t make you a virgin forever.

Your virginity is yours to define. So make your list, then start checking it off. I’m happy to help out when I come visit ;)

- 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.