My experience with self deprecating humor is that it only works well when the audience has sufficient context to get why it is funny. Otherwise it just comes across as poor self esteem and signals that you really are the loser you are claiming to be.
I like the suggestion someone else made to basically joke about life, not about people. (my words, not theirs, but that's what it sounded like to me)
I like the suggestion someone else made to basically joke about life, not about people. (my words, not theirs, but that's what it sounded like to me)