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Dear Stephen,
I’m in the middle of some gay drama. My ex-boyfriend “Kyle” is a jerk. [Editor’s Note: I changed the word he actually used to describe Kyle, because my mom reads this thing.] He was a lying, cheating, gaslighting manipulator for our whole relationship. We broke up in 2022 and don’t talk anymore.
He has since had another relationship with “Peter.” Apparently they broke up because Peter appeared on my Hinge last week. We matched and are messaging. Turns out he had the same experience with Kyle and finally left him over the holidays. TBH, I first matched with him to be petty, but we have a lot in common (besides our ex, lol). Should I ask him out or is that too far?
—Small Town Gay
Dear Small Town Gay,
When I first read your letter, my gut feeling was: You might not be going on that date out of vengeance, but can Peter say the same? For you, Kyle is a distant ex. For Peter, he’s a much more recent one. Is there any chance Peter is using you as a pawn in a revenge scheme of his own? Or, even if it’s not that calculated, does it maybe say something negative about Peter that he dumped a guy and then immediately pursued his ex? And do you really want to take any action that could bring Kyle’s toxicity back into your life?
But then I read your name: Small Town Gay. Oh.
It’s hard out there for small town gays. The dating pool is, well, small. And I think in that context, it’s normal for guys of similar age and type to date each other in various combinations until they find the right match. Is it messy? Yes, and my concerns above still stand. But if this guy’s a good prospect in a town without many, it might be worth the risk. Just proceed with caution. And maybe let the dust settle on his breakup before meeting up. If he’s meant for you, he’ll still be around in a few months. Take a beat, then go for it.
Dear Stephen,
My boyfriend told me he doesn’t like my art. I am a watercolor artist by trade. For his birthday, I did a painting of his dog. Months went by, but he never hung it up.
When I asked him about it, he kept saying he hadn’t gotten around to it, but eventually admitted he doesn’t like it as he doesn’t think it looks like his dog. I took it back. I love him and he is usually quite supportive of me. But this bothers me as it feels personal. What should I do?
—Watercolor Waterworks
Dear Waterworks,
I get why it feels personal. Art is personal! You took a part of yourself and put it onto paper. He should have accepted it with gratitude and displayed it.
But!
I would be doing you a disservice here if I told you to stay mad about this. It sounds like he was caught off guard by unexpected questioning, and said something really stupid as a result. It’s helpful context that you love this guy, and that he’s usually in your corner. That makes me think this was more awkwardness on his part than malice.
It’s also worth noting that, based on your own account of the conversation, he did not actually say he doesn’t like your art! He said he did not like that one painting because he doesn’t think it looks like his dog. Again, I do not think he should have said that to you. It’s rude. But it’s a narrow statement. Don’t go wide with it.
I’d bet your boyfriend still admires your art, even if he thinks you did not nail the proportions of his Labradoodle’s snout, or whatever. People are kind of nuts about their pets. In time, I suspect it won’t feel as personal.
DRAWING BREAK!
Speaking of art, here's a drawing I did of a crab and a seagull in love.
Dear Stephen,
How inappropriate would it be for me (31F) to ask out a coworker (30M) I have a crush on? We have a connection that feels like more than friends. We work in different parts of the office (on different teams that rarely interact) but we always make excuses to come talk to each other. It feels like there’s a spark between us.
I think he would say yes if I asked. I’m just not sure if I should go there since we’re coworkers. What say you?
—Feeling Like Pam Or Maybe I’m The Jim
Dear Pam And/Or Jim,
I say go for it. Your HR department may not agree with me, so I guess you should consider their opinion too. But my feeling is this: There are only so many places to meet people in this lonely world. If work can’t be one of them, what’s left? The club? You’re in your 30s, so you might not be going there much. The gym? Don’t make me sick.
My advice would be different if you worked closely together, as you’d need to consider how you’d handle collaborating under both the best case scenario (do you really want to make sales decks with your partner all day?) and the worst case scenario (would you be able to work together if you broke up?). And my advice would be very different if one of you was in charge of the other. Do not ask out someone whose career is in your hands, obviously.
But it sounds like these are not concerns here, so I think you can shoot your shot. Do it in a chill, no-pressure way — ideally off the clock and off company premises — and make it clear that if he says no, you won’t be weird about it. Which reminds me: If he says no, don’t be weird about it. I hope he says yes! Good luck.
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