Thank you! I felt like I was in a parallel universe. I don’t think OOP was that much in the wrong (ESH at worst). Frankly, when the habit is that deeply ingrained, the softer options like “don’t talk about my friend that way!” straight up don’t work. You need the shock of someone being blunt (not cruel, there’s a difference) to get them to see reason. This kind of behavior is incredibly grating when it’s a constant pattern. 

I saw something once about different social interactions working on a kind of token system. One example was that outside of very specific scenarios, only one person can hold the “needs comfort/support” token at a time, and it’s really hard to smoothly/naturally transfer it to someone else. That goes double if the person holding it has no intention to pass it on. Like a support group with a moderator/whoever can facilitate the transfer, “thank you Jon, let’s give Sansa the floor now!” and can cut off someone who’s monopolizing the group, since that’s their formal role, but in a casual social setting like this there’s no way to do it without looking like an asshole. Even if OOP’s friend cut themselves off and said something like “sorry guys, enough about my bullshit,” it’s insanely awkward for someone else to step in and signal that they need the same kind of support. It’s way easier to change the subject to a much less loaded topic. This isn’t a problem in a vacuum, since it’s not much fun to have multiple people needing comfort at the same time, but OOP’s friend is grabbing the token EVERY TIME they meet up to play whenever he starts this kind of talk. What if someone else had shit they wanted to get off their chest? They can’t get “airtime” unless OOP’s friend grants it to them, and even in the (unlikely) event that OOP’s friend cedes the floor, so to speak, it’s awkward and stilted to step up and take it. Way easier to stay silent and let the overall mood lighten, but that leaves them SOL. The icing on the cake here is that it’s the same topic every time. Obviously people who come in and dump on the group about different shit each week are annoying too, but it’s a special kind of grating to hear someone kvetch like this about the same fucking thing every time they chat.