Every woman is different of course but in general I go with sarcasm, redneck humor, and sometimes toilet humor.
I also make fun of technology a lot, and make jokes about peoples' dependency and addiction to it.
If a woman asks me what I do for a living I generally say "Kelvin Klein Model" or "Chip And Dale Stripper".
I will make fun of myself like how I seem to always end up with crazy women, but I never make fun of my appearance, cloths, etc. I am always c0cky about that. Here is something that just happened:
Earlier this past week I had to get up b@lls a$$ early for work one morning and I put my shirt on inside out! A male coworker pointed it out in front of a female coworker, both are friends outside of work who I hang with regularly. He said "Is that shirt inside out Lefty?" I responded back "YEAH it's inside out... Haven't you heard, this is the new Hollywood trend now? Everyone is doing it. Where have you been?". The female said "yeah whatever I have never heard of it". I said "So are you an expert in male fashion?" The male said "Oh yeah I have heard of it, Female, where have you been?" We had her nearly believing it!! It was fvckin hysterical!! I kept frame and kept it inside out all day too.