I'm pretty sure there's still a funny bone hidden in there somewhere! Don't give up, Redskinsfan! I think what you need is not more humor, but less inhibition. Inhibition ruins everything. It blocks your mind, makes you utterly blank, and prevents you from generating any sort of comeback until after the conversation. -_-
I think that before one can truly be free and outgoing, he must accept and likehimself first. You know, being comfortable in one's own skin and all that. After that, the wall of inhibition comes crashing down and the humor and the witty remarks follow naturally.
The problem is how to get there.