Outlier
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Understanding the context of something doesn't mean someone will accept anything that comes from it. Like, we know that sometimes men will catcall and make gross gestures and say threatening things to women as they walk down the street or sit on the subway. They may laugh and make jokes at someone's expense while making them uncomfortable. That's the context, but knowing it doesn't make it any better.
That's more extreme than, say, a comedian on stage or course. There's a spectrum of contexts that range from wanted and expected (like going to see a comedy performance by a comedian who you already know is known for racy jokes) to unwanted and unexpected (like having strangers accost you, making jokes based on your race, gender, etc.) and a lot of grey area in the middle.
Most of what you're describing sounds like sexual harassment to me. Trying to be "funny" doesn't give you the right to harass or threaten anybody. That goes without saying. There are laws in place to prevent those kind of things from happening.
I thought this thread was about jokes.