Humor COMBINED with arrogance?

I'm trying to develop the "attractiveness" that women desire, I'd like some assistance in understanding an intriguing discovery. This is under the flirting category because I will only be speaking of the initial approach of appearing attractive, within your personality, and NOT about "future potential".

When someone points out a "quirk" or insecurity within a woman, in a playful manor- it seems to spark a trigger within the woman I've been talking with.

- This is the "discovery" that I've made, rather than being the cookie-cutter of a guy that approaches using "Whoa I really like ___" or his own line.

What'll it be- is it truthfully playful and acceptable to be a funny while being arrogant about your self-knowledge (and not your self-image)?
Humor COMBINED with arrogance?
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