How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
I am 36, gay, and single. I am always down for a hookup, top or bottom. I recently hooked up with an attractive older man, in his mid-60s, who is in an open relationship. We had a great time and have hooked up several times since then.
This last time, though, his partner came home during our hookup.
He left the room briefly and had a quick conversation with his partner. When he came back, he said we were OK to continue. Not a problem, we finished. It was great. On my way out, I ran into his partner. My surprise when I was face-to-face with my high school English teacher, who I hated and hated me. I almost didn’t graduate because of him. We had no less than five meetings between him, my parents, the principal, the school board, and the school counselor.
He didn’t say anything and maybe didn’t recognize me. But I recognized him. It killed my mood. Now I am worried that it has soured one of my favorite hookups. Should I just drop it? Say something? Find another good daddy to pin me to the mattress? Help please!
—Not Hot for Teacher
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Jessica Stoya: High school was 18 years ago. Your grudge is about to graduate from high school itself.
Rich Juzwiak: That’s true, if it wasn’t held back.
Jessica: Oh, boy.
Rich: There’s no obligation here. So it’s up to the writer’s comfort level. In other words, I don’t really even see the problem. It soured his mood? OK. You just came face-to-face with someone from your past that you had issues with? Well, you could host it at your place if you want to keep that from happening again.
Jessica: It seems like the issue is completely internal. So the series of actual questions can be summarized as, what should I do here? And our dear writer is the only person who can answer that, because they should do what feels appropriate.
I wish we had nuance about this whole grudge and knew more about why he almost didn’t graduate because of this teacher.
Rich: They’re both queer, let’s say. So that’s an interesting feature to this. This kid in high school, who’s at least pre-gay, is having conflict with another guy who has sex with men or goes on to have sex with men. As opposed to a mentoring situation, there’s a conflict there.
Jessica: It could be anything from the English teacher was really pedantic about the Oxford comma and working out some anger issues in a way that the Care and Feeding column would take huge and justified issue with, through to, say my ninth grade English teacher gave me a 98 percent on a paper once because I used a word she said wasn’t a word, and I came back the next day with a Post-it note flagging usage of that word in the textbook, two different dictionaries, and an example from English literature using it.
So I’m very open to the possibility that our writer was like I was in high school and might have, through naivete, brought some of that hatred upon themselves. It was definitely not a comfortable situation for me and, very much obviously in retrospect, not for my English teacher either. So, think back. Was there maybe some kind of disconnect between how to approach authority figures that, in the cold light of adulthood, maybe explains some of the tension?
Rich: Yeah. Otherwise, this is a great revenge scenario for you. This is somebody that you hated that had some authority over you, and now you get to—I’m going to say it—fuck his partner. So this is your way of getting revenge later, or just a one-up on him.
Also, if that’s too much, if you don’t want to run into this guy and you can’t host for some reason, the good new is: You’re always down for a hookup, top or bottom, and you’re hooking up with a guy in his mid-60s, so you have, it would seem, a broad range of potential people that you could hook up with. This union you have with this person is very low stakes. Move on to somebody else. You could find somebody who isn’t in a relationship with your high school English teacher—there are a lot of those out there—and then you’ll be fine.
Jessica: Yeah. Take a minute, and think through why this thing from 18 years ago is really still under your skin, and then consider whether you want to drop it and keep seeing this guy. Do you want to say something? Is that something maybe a “Hey, can we talk about 18 years ago when I was a child?” will help diffuse. I agree, it should be very easy for this guy to find several other good daddies to pin him to the mattress.
Rich: If somehow you have to interact with the partner again or find yourself interacting with him, pretending like everything is all good (it’s so long ago that probably all of this stuff has faded away for him) could work. You could just be cordial to each other. You can both say, “We knew each other in a past life, ha, ha, ha.” That’s all it would have to be.
So again, this is a potentially dramatic situation if you want to take it there, but if you don’t, it certainly doesn’t have to be. My advice to basically every question I approach is to avoid the drama. Don’t make life more complicated and uncomfortable. Just don’t do that to yourself.
Jessica: I mostly agree, unless our writer is really certain that they did nothing egregious, and the reason this is still under their skin nearly two decades later is that the English teacher acted egregiously. Now, confronting someone about this usually goes extremely one way or the other. Big gamble. You might get, “Yeah, I was right. I’m doubling down now. How dare you even think to bother me with the information that I treated you in a way that is still hurtful?” But also, sometimes people are like, “Oh God. Not that excuses or explanations are going to necessarily help, but if you want to know why I was acting like that, I can explain. I regret it, and I’ve changed.” Sometimes it’s a gamble, but it’s one worth taking.
Rich: You might get closure there that you never saw coming. This is still on your mind 18 years later.
Jessica: Yeah, but if you take the bull by the horns and the English teacher doubles down, you’re not hooking up with the partner again.
Rich: Right. So, tread carefully.
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