#1063: Is this all-in-good-fun old-timey-cosplay flirting or weird boundary-pushing flirting?

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?

Hi there, friend, thanks for sharing your story.

This guy’s costumed flirting may be totally in-character, normal for the events you attend and “harmless,” but that doesn’t mean you have to keep go along with it if it makes you uncomfortable. There are lots of ways to respond and stay in period and in character, for instance:

Video description: In a scene from Whit Stillman’s movie adaptation of Love & Friendship (one of my favorite comedies of 2016), Lady Susan (Kate Beckinsale) and Alicia Johnson (Chloë Sevigny) wear fancy late 18th century costumes and gigantic hats as they stroll and have a conversation. A well-dressed man approaches and tries to get Lady Susan’s attention. She responds, “How dare you address me sir! Be gone or I’ll have you whipped!” Alicia says, “Outrageous! Have you never met him?” and Lady Susan says, “No, I know him well. I would never speak to a stranger like that.

You don’t have to go to Lady Susan’s ridiculous satire extreme, but you also don’t have stand there meekly putting up with it or participate in it if you don’t want to, and you definitely don’t have to engage with it just because you did in the past. Find the level of conversation that you are comfortable with and work from there. You don’t owe this guy or the surrounding onlookers a specific kind of performance just because he’s giving you one, and you don’t owe him any apologies.

Going back through your history, it sounds like you’ve been routinely straightforward and honest with this guy and that any problems between you result from his inability to be equally straightforward with you and others. You’ve said directly, “I’m willing to consider being friends again, but I don’t want to flirt anymore.” Since then he’s tried to push past that boundary in more than once both in and out of costume, and then he’s also tried to get you to reassure him about it by telling you about his dream.

Enjoy this illustrative Portlandia sketch:

Video description: In a conference room meeting, a man (Fred Armisen) announces that Kathleen Drake (Carrie Brownstein) will be the first female partner in the firm’s history. Kathleen gives a speech and mentions some of the struggles she’s had as a woman working at the firm. All the men in the room interrupt her speech, one by one, to ask her for reassurance – “Sexism is a problem, but, I’m not bad, right?

He feels uncomfortable and like you might be repulsed by him. Hrmmmmmmmmmmmmmmmm, why is that, I wonder? Is it because you told him you didn’t want to flirt anymore but then he kept flirting with you? I DON’T KNOW, IT’S A MYSTERY. Is it because he sat uncomfortably close to you and kept brushing up against you like an over-friendly cat? WHO CAN SAY, LETS CONSULT THE ORACLE. Is it because you told him what your boundaries were and then stuck to them and then he made you feel like you had to constantly patrol them and could never relax in his presence? MAYBE THE ENTRAILS OF THIS GOAT CAN TELL US, IF NOT WE’LL PROBABLY NEVER KNOW. Is it because he is trying a “but you’re so beautiful and charming, I can’t help showing it” gambit to make his behavior at least partly your fault? SO CONFUSING, WHAT A RIDDLE.

You’ve already told him what you need in order to be friends: An end to flirting. This isn’t hard or confusing or unclear. Even in ye olden days of fancy hats and formal manners, men had conversations with women that weren’t about flirting or exaggerated shows of charm or chivalry. Presumably there are other men at these gatherings that he talks to, and presumably there are conversation openers along the lines of “Verily, yon vicar’s sermon was most enlightening today, was it not?” or “Read any good passages from Fordyce’s Sermons or Sinners In The Hand Of An Angry God lately?” or “Would you care to make up a fourth at Whist?” that can be delivered without a suggestive eyebrow raise. Flirting might be his habit, “just his way,” a central pillar of his personality, a thing he really enjoys, an accepted vibe at these gatherings, etc. and he can still figure out how to interact with you in another way and not use the event as a smokescreen for stroking his ego at your expense.

Incidentally, his recent email about his dream doesn’t seem to have contained an apology anywhere. He wants reassurance from you but not responsibility.  He can’t even address it directly, it has to come in the context of you reassuring him about a dream he had, when, buddy, your dreams are pretty much between you and yourself and don’t obligate people to do or say anything about them. He enjoys flirting with you and wants to keep doing it and he can’t help it because you’re just so great. And like, you ARE great? Super great. And you don’t like flirting with him, and you’ve told him that, and you have done enough emotional labor for and around this dude for one lifetime. 

In your shoes, I’d probably try one of two things:

A) Delete the email, never answer it, and let him marinate in his uncomfortable feelings literally forever. Let him worry about how to interact when he sees you next. Let him worry about the mutual friends and how to not make it weird. When you run into him at events say a brief hello and then focus your time on other people. If he deputizes mutual friends (ugh) or his fiancée (UGH!!!!!!!) to come talk to you on his behalf just say “Yeah, he sent me a strange email about that a while back, I figured it would let everyone save face if I just ignored it. Anyway, new topic. How are you? Wherever did you find the ribbon for that excellent bonnet?” 

B) Write back once and say some version of “I’d love to be friends, but I don’t enjoy flirting with you. If you want to be my friend, please figure out a new way of interacting with me so we can be done with exhausting conversations about it and I don’t have to be on eggshells when we see each other at [events]. Thanks.” Return the awkwardness to sender.

Whatever you decide to do, I give you permission to stop worrying about this guy and his feelings anymore. You made out once…four years ago. You’ve already forgiven him for some bullshit and told him how you needed things to be. You shouldn’t have to keep negotiating this! He’s the one making this weird, and he’s the one who needs to figure out a new way to relate to you if he wants to be in your life at all.

Moderation Note: I have a) a monster cold and b) a giant-ass pile of grading to get through this weekend, so no comments on this one. The forums at friendsofcaptainawkward.com doubtless stand ready if someone wants to start a discussion there.