[TDawg4]

Personally, I just regret all the dumb shitty edgy humor I used to pull in those game nights.

I think it depends on the setting. I have made pretty edgy jokes with the wrong group of people, but just this week made a joke to an old lady I know. Something about a moving company needing a bigger box (a casket) if they are going to put her in it. After she made a comment about fitting in one of their boxes. This worked well because of the types of jokes she makes I was able to know that she would take it well and appreciate the humor even as morbid as it was. 

This being an example of ^shock type 1. I don't actually want her to die ect ect.

I could think of other example like when I played on an all hispanic soccer team in high school except for me. There were so many gringo jokes ect ect flying around during games with my team but it was always super fun. But when other teams made comments my teammates defended me. 

I for sure can think of really dumb edgy jokes I have made that ended up hurting people because I didn't understand the context or have a good enough relationship with that person.