rdor said:If I can butt in and add something; self-deprecating statements, including self-deprecating humour are best avoided when speaking to women. It generally doesn't come off well.
You may think you're being cute, clever and self-aware, but all they see is "guy with no confidence."
I might believe that, if Conan O'Brien--the master of self-deprecating humor--wasn't so successful.
There is an audience for this kind of thing, and I would suspect even some women don't mind it. Personally I tend to like it when girls show this side of themselves, it shows humility, which is always a plus for me.