Hmm, I get what you're saying. That was always the struggle with my humor - I would bring up social problems like stereotypes and racism, even though I didn't believe them. For example, I would make a joke about Mexicans because I knew it would get attention, but I have no problem with them. Of course, I would get the cynical people to join in, and the people who thought I was racist to scorn me.
Maybe if I had friends I could trust, I wouldn't worry about this stuff so much.
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