I don’t know if I have a clear answer to how I learned and practiced this. Probably a lot of simple exposure and observation. The important thing is the friendship comes first; I never make an insult joke to someone I don’t know well. I build a friendship first, then test out the waters with small jokes.

I also always start and focus on myself; I make jokes at my own expense often. A big part of my personality is a strange juxtaposition of bravado and self deprecation. I will joke about how amazing I am and how much of a failure I am at the same time.

It seems to work? I think people like me, generally? I don’t know man, I just wing it! I have no idea what I am doing, but I am also pretty great at not knowing what I am doing.