When to use "****y and funny" is often a matter of timing...of accurately reading the current circumstance...and of having SOME general knowledge of the demeanor of the woman you're using it on.
I would say that there are MULTIPLE fine lines between being witty and being an asswhole, and "****y and funny" is somewhere in the middle. But if you use it in a way that comes across a little TOO mean-spirited to the the other person, then that's when you get all that NEGATIVE feedback.
Most people are at least a little "self-conscious", and maybe WOMEN even more so...That's why SARCASM can be a volatile weapon to use in your arsenal to attract women. Sarcasm is a higher form of humor in the sense that IT, unlike some other forms, REQUIRES a certain level of mutual intelligence for BOTH parties to enjoy it...
...if the delivery comes across as the slightest bit insulting, it could explode in your face and blow away ANY attraction that you may have nutured with the woman.
So let's be CAREFUL out there,troops...