How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.com. Nothing’s too small (to ask).

Every week, the team answers a bonus question in chat form.

Dear How to Do It,

An occasional time-waster of mine is to go into random text-only chat rooms and spin a fantasy for a willing woman. It’s fun and creative and everyone has a low-commitment good time (I hope). Recently, someone online asked if I would do a “losing her virginity” scene with her. I said sure, and I took her through a very sweet and consent-filled fantasy where she got to direct the action and feel like a star. At the end of it, she confided in me that she is actually 16 and really a virgin and also, would I want to meet up to do this for real? I of course said that I didn’t think this was a great idea but that she would make a great partner for someone someday. (I am well over 16.) But now I’m conflicted and totally gun-shy about going back online. I know, of course, that whoever is on the other side of the chat could be a boy/girl or a nonbinary/furry person of any age or orientation, but this definitely made me uneasy. Did I do a wrong thing? Is there a better way to proceed? Or should I just be happy she had a nice experience in her own home with a faraway guy who hopefully gave her a template for how it could go when she finally finds herself ready to have sex?

—Elder

Rich: “I thought she was of age” is, if not the, then one of the oldest clichés in the book. But I think the thing here is that there was no discussion ahead of time at all?

Stoya: So … men sometimes do this thing where they treat the world like it’s their sex Disneyland. (I should say #NotAll, and also that this isn’t just men … I’ve definitely done it myself.) This guy really, really, really should have been asking for ages before proceeding with these cyber fantasies.

I’m not trying to dictate feelings here, but uh, no. Don’t be happy.

Rich: It seems almost convenient that he didn’t ask, but also that he didn’t seem to immediately absorb that’s what he should be doing. “Is there a better way to proceed?” Buddy, you just walked into what not to do, and avoiding that issue in the future is really clear (to me, at least!).

Stoya: There’s another thing guys do, which is ask for absolution: “Is it creepy if … ?” Or basically, “I did this thing, and want to be told I’m still an OK human.” Therapists and sex workers see plenty of this kind of behavior. In my experience, the reactions are pretty traditionally gendered. Women tend to go all the way through to “I think I messed up by … ” This way—his “Did I do a wrong thing?” way—feels a bit cowardly, and like he’s avoiding something. Like accountability.

Rich: Yes. I might be a little more sympathetic if not for the actual details. Wasn’t he already treading in barely legal territory with a virginity-loss fantasy? And then when he found out her age, he still had a conversation with her, ensuring her that she’d make a good partner, thus continuing the fantasy?

Stoya: I just … He should’ve shut it down immediately when he found out her age.

Rich: Yeah, I totally agree. Closed the window. That’s it. Don’t even say goodbye.

Stoya: Agreed. I’m going to go ahead and say it: Yes, you did a wrong thing, letter writer. The only acceptable way to proceed is to ask someone’s age upfront before anything gets sexual. You should just be happy you didn’t end up on Dateline and are decent enough to have shut it down before you committed a major crime. There’s no upside. There’s nothing to congratulate you on. The best you can hope for is the absence of harm.

Rich: Which is a distinct possibility. But I can’t believe he’s trying to pat himself on the back to the very end: “ … Should I just be happy she had a nice experience in her own home with a faraway guy who hopefully gave her a template for how it could go when she finally finds herself ready to have sex?” I’m not trying to dictate feelings here, but uh, no. Don’t be happy.

Stoya: The word finally there particularly irks me. Sixteen is not an appropriate age to apply “finally finds herself ready to have sex” to. Twenty-five maybe? Twenty-five might be a “finally” situation.

Rich: I got a letter from a 56-year-old virgin last week. “Finally” is her theme song.

Stoya: That’s definitely finally.

Rich: It seems very clear-cut that a brief discussion of age could be had before engaging in these chats again without losing anything and gaining a barge full of confidence that a wrong thing will not be done. You know, there have been times, not recently, that I carded Grindr guys. You gotta be sure!