I’m either really late genX or really early millennial depending how you define it, but Pump Up The Volume was the one that did it for me.

Schrödinger’s asshole. It’s testing boundaries. If you say something, they’ll claim it was just a joke. If you don’t they’ll keep going and likely get worse.

I have the same thing. Someone once called it “resting murder face” because apparently if I forget to smile I just look like I want to stab someone. That plus having a deadpan sense of humour and generally flat tone of voice makes me come across as a total asshole unless I make extra effort. Even when I’m sincerely trying to be nice people assume I’m being sarcastic.

I haven’t been in the loop since 2016.

Not really. They have a lot of bits and in-jokes which are going to seem incomprehensible to anyone from the outside, but most of them are pretty chill if you engage in good faith. It’s like a lot of tech communities; if you don’t do your research and ask intelligent questions, you’re likely to get told to RTFM.