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True, most of the cocky & "funny" stuff doesn't seem that funny to me at all. Neither do most sitcoms. I'm into comics like Louis CK, Mitch Hedberg, and Demetri Martin. I find self deprecation hilarious, and I can picture myself being like them, but not someone like Dane Cook.
It's possible to pull off self deprecation...but i wouldn't want to.
You've already stated originally that you've learned that your brain is flexible. I would urge you to stay positive. It just takes practice to make this as natural as being negative and people really like being around folks that are positive. I would even bet that you'll like the people it attracts, too.
I'd bet there are places either online or with your local musical community to find venues to explore clear, word smith like ways to express your abstract thoughts and get to know more people that have similar brain processes.
If it doesn't exist, make one. Start a composers club or something... You'll get first access to anyone who joins. This will force some social skill progress. You're also in charge of something interesting. That makes you interesting! Milk it!!!!
It's hard to find regular people to handle deep abstracts. Your average chick in a bar isn't likely to follow an analyzed view of music theory, but the average chick in your local community collage orchestra just might.
Peace
Kisser