Dear Captain Awkward,
Four years ago, the first fling I had after I left my ex was with a guy at a large multi-day costume event in a far-off state. He came on really strong (in character) and as we have friends in common, I knew he was engaged and asked him about this. He eventually explained to me that he had permission from the fiancée to fool around above the waist, and as this is pretty common in our circles, I liked him, and I was about to go back halfway across the country, I figured what was the harm to have a little fun?
So we made out a little, and kept writing to each other flirtatiously after I went home. I wanted to come back for the final weekend of the event, and he offered to put me up at their home. I had been pressing him to tell her about us, and he said he was waiting for the right time, finally saying we’d all go out when I got there and he’d tell her then.
Long story short, “circumstances” intervened so that he never told her, she found out and chewed me out (with him standing there not stopping her), I had to find another place to stay in the middle of the weekend, and I was livid with him for ruining two potential friendships (with him and her) and cut off contact with him.
Months later she wrote me apologizing for yelling at me, said they had both worked everything out, and asked if I would consider being friends with him. I said yes, as long as he agreed never to flirt with me again.
Now he is a bit of an unusual guy. The characters he plays in these costumed events tend to be overly chivalrous and attentive to women (opening doors, pulling out chairs, getting the check) and that tends to carry over in his real life (he also has a lot of hobbies related to historical re-creation and crafts, and tends to like vintage things generally.) So what I might read as creepy boundary-pushing attention, due to the massive breach of trust he committed, others have just told me they see it as flirting/overpoliteness/old-fashioned aesthetic, and don’t really have a problem with it, just see it as harmless.
He tends to fall back on flirting-as-a-social-lubricant, because that is his comfort zone. He flirted with me a couple of times when we bumped into each other at a costume event after we had reconciled, but we also had drinks recently, out of costume, where he behaved himself.
As a modern woman, I don’t like pro forma chivalry in my normal life, but I can go with the flow of being “treated like a lady” at historical events if I know it’s all pretend. But with him, it rankles because I’m not convinced it’s all an act.
Recently I went again to the same event and spent a little time talking with him in character (during which he fawned a lot, flirted, and then apologized for flirting when I seemed to be bothered by it) and afterward, we went out with friends, during which he sat next to me, suggested we order stuff to share, and seemed to find excuses to brush up against me, which made me super leery. Usually, when he oversteps, I call him on it, but I didn’t do it during dinner because I didn’t want to have the big awkward conversation with friends there, and the breaches were slight enough that it felt like it wasn’t worth it to correct him.
So, since for the last few years he’d done little to restore my respect for him, or given me any consistent reason to trust him or his promise not to flirt, I made up my mind that I was done seeking out his company, although I’m okay with an occasional brief friendly interaction, and as we don’t run into each other very often, that’s not really hard to accomplish.
But he wrote me a couple weeks after that saying he’d had a dream about me being repulsed by him and was worried it was his subconscious telling him he had overstepped, and wanted to check if everything was ok between me and us. He said he admired my charm and talent and also liked me a lot, and that it was hard sometimes not to show it.
I’m not sure how to respond, or if I should. I’m going to be around his neck of the woods a lot next year and I’m worried about possible future interactions, especially since I like going to costume events in the area and we also share a group of friends.
A pretty timely problem to have, considering open and vocal disdain for creepiness is currently in the zeitgeist.
What do you think?