Ask Agatha: My Old Teacher is a Regular at My Gay Bar

Dear Agatha,

So, here’s a situation I never thought I’d find myself in. I’m 26 now, living in a new city and, like any self-respecting gay man, I’ve found myself a great gay bar that I frequent with friends. I love the vibe, the drinks are strong, and the crowd is... well, let’s just say it’s a good time.

But here’s the thing. One of the regulars at this bar? My old high school math teacher. Yeah, that math teacher—Mr. Fletcher. The one who handed me back my failing algebra tests with a sympathetic look. He was in his late 30s when I was in high school, which would make him about 45-ish now. And honestly? He’s aged well. Really well. I never thought about him “that way” back then, but now? Let’s just say I wouldn’t mind doing some... private tutoring.

We’ve made eye contact a few times, and he definitely recognizes me, but neither of us has said anything. Here’s the thing: I’m interested. Like, seriously interested. But I don’t know if pursuing something would just be way too awkward, especially with the whole former student-teacher thing. I mean, it’s been almost a decade, and I’m a full-grown adult, but still… is it weird to go for it? Should I make a move or just let this crush fade like my memories of algebra?

Help me out here, Agatha!

Sincerely,

Confused in Calculus

Dear Confused in Calculus,

Oh, honey, I have to admit I’m living for this scenario! Nothing spices up a casual night out at your local gay bar like running into a blast from your academic past—especially one as handsome and aged-like-fine-wine as Mr. Fletcher.

First things first, you’re 26 now, which means we’re out of the realm of inappropriate territory. You’re not a high schooler anymore, and he’s no longer grading your homework, so let’s remove that little roadblock from your mind. The dynamic has changed, and this is simply two grown men at the same bar—one of whom is, apparently, very good at math and equally good at keeping things tight over the years. Props to him!

Now, you asked the big question: should you make a move? And my answer is: why not? Life is too short to let a few awkward encounters at a bar stop you from possibly unlocking a new chapter of, ahem, extracurricular activities. If you’re feeling the vibe, and you’re getting some return glances (which sounds like you are), then what’s the harm in striking up a conversation? Maybe he’s been waiting for you to break the ice and isn’t sure how to approach you without coming off as, well, creepy.

That being said, be prepared for a bit of awkwardness at first. The student-teacher dynamic might still be a little fresh in his mind, especially if he remembers you sitting in his classroom, trying (and apparently failing) to solve equations. He might be hesitant to cross that line, or he could have his own personal reservations about engaging with a former student. And that's totally fair! You’ve had time to process your feelings about the situation, but this might be new for him.

I say, start slow. Next time you see him, catch him at the bar when he’s grabbing a drink and give a light-hearted “Hey, Mr. Fletcher—small world!” comment. Ease into the conversation. Talk about how life’s been since high school, catch up on the basics, and feel things out from there. Trust me, darling, if there’s any chemistry lingering in the air, you’ll know soon enough. And if he’s still hung up on the teacher-student thing, you’ll know that too.

But here’s the thing: you’re two adults now, in a space that’s made for fun, flirty, and sometimes downright steamy encounters. As long as you’re both on the same page, there’s absolutely no harm in seeing where things go. Just don’t be too disheartened if he’s not quite ready to mix his algebra with your calculus just yet. Who knows? Maybe all he needs is a little time to adjust to the fact that the kid in the back row has grown into a confident, handsome man who knows exactly what he wants.

So go for it, babe. You’ve got nothing to lose except a little awkwardness—and maybe a chance at some advanced lessons in... well, let’s just say more than math. 😉

XOXO,

Agatha 💋