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The original was posted on /r/twoxchromosomes by /u/CoffeeCakeGod on 2023-10-04 14:47:56.

My best friend, cait, and I play videogames together over discord pretty much every other night, usually her, myself, and two of my friends in a party. She has a boyfriend, we’ll call Edgar, who tags along. They have been dating 2 months, talking for 5 months.

Edgar constantly makes these pointed jokes to me and my friend. Cait is hard of hearing so he’ll say things like “wow, you’d think you couldn’t hear.” If she misses a call out. I’ll stream for her if she’s doing work but still wants to see game play for something. Hes always near her and doesn’t like my desktop icon arrangement I’ll hear him say “wow, I feel like I’m in a pigpen looking at your screen” over her mic.

Cait’s told me it makes her feel kind of bad bc she hears his jokes constantly, but he says he “bonds” with people over jokes because they “know he doesn’t mean anything by them.”

That last part is where I get confused. No one laughs at them, we usually just tell him to shut up and move on. She’s explained to him that she has anxiety over her hearing and hates the “joke” because it makes her more paranoid she’s missing things, but he continues to make the jokes because his intention isn’t to hurt her and she needs to ‘get used to’ his banter.

I love roasting people and banter, I truly do, but none of the shit he says is ever actually funny. It’s more annoying than anything. Constantly saying the same jokes to no one, not even him, doing anything more than a forced laugh. He’ll smirk, that’s about it.

Here is my active question, how would you go about having a conversation about this with him? I don’t think he’s unreasonable, I think he has very little friends and his socialization has revolved around these awkward ass jokes. Him and his friends obviously joke about each other’s insecurities with these lame “wow [insert joke]” one liner formats. They talk/get together (according to him) maybe once a month so perhaps they think it’s fresh and hilarious everytime. It’'s mind numbing. He keeps saying he is a roast master, but is “holding off” until we’re “used to his humor.” I wish he’d make an actual fucking roast so maybe we’d laugh for once.

Neither of us want to react with anger or accusations, but seriously question if approaching this with calmness and empathy will actually change anything bc she said she already did. She’s hoping if I say something too, that Edgar will realize she’s not just “being sensitive.” I thought about saying “what’s funny about that” every time he makes one of these jokes to have him seriously explain but he’d probably make another joke saying “you just don’t get peak comedy.” Other option was all of us starting to roast him for his jokes, but that seems wrong and alienating bc we would be doing it out of spite. Yes, normally I’d say she should handle it since it’s her relationship but he’s bringing it into my life and friend group too. Plus she’s my bestie of 12 years so

Reddit, wwyd

Tldr; My girls man is goofy asf but thinks he’s the next Matt Rife for making jokes about people in the format of “Wow, [insert observation or joke].” How would you convince him to cut back or get new material while realizing joking about my friends insecurities isn’t the knee slapper he thinks it is?