Does cocky and funny work if you are a good looking guy?

Just want to start by saying all you guys are great and all advice is welcome.
I am a good looking guy. Not being conceded. I've dated many beautiful women, but I want to be a master. I think I have a long way to go. Sometimes when I am using cocky & funny humor ect. I get insecure reactions. Not always, manly on the less attractive women, but sometimes even the really hot ones come back offended. It seems only 10% really take it and run with it. They know how to kid around. Do any of you do any Comfort building, before teasing?

it should work, but i think you should tone it down on being cocky...
one thing i always keep in mind is... "if someone came up and said that to me, how would I react/feel?"

Well, Jester has a point.

You are probably rushing with the cocky/funny.. which ultimately is to start creating attraction.

Approach, make them confortable, warn them before about been a "confident" type of guy, so they have an idea of what is coming, and have fun!

21, always get told I look like "the situation" and rockin the bad boy look. I know cocky funny works for us bro. You just gotta hype up your energy and up the ridiculousness of your sarcasm to let them know you're just having fun. Obviously we cant use a lot of the cocky funny lines like, "I'm just gonna have a salad, I'm watching my wasteline" It works for a chubbier guy because she knows he's kidding, but for us it sounds like we're way too serious about our looks. Get it?

cocky funny only works if you are smiling and it is obvious that you are not being mean. Being mean sucks.