It really comes down to a few things.
Is he already in love or in a committed relationship?
Is he attracted her?
Is she looking for sex/fun or marriage?
Does he want what she wants?
The reality is everyman dreams of having women throw themselves at them. Rarely does the average guy get flirted with, asked to dance, or pursued in anyway by women.
They believe a guy has to be "extremely good looking", "rich", or "famous" to get women to pursue them.
One of my theories about why many men enjoy watching porn and going to strip clubs is they get to experience the "fantasy" of having women "hit on them" or made to feel sexually desired.
Most women aren't willing to risk (rejection) or they fear a man will take advantage of them. And yet men are "expected" to put themselves out there for women to be rejected, offer to spend money on dates, and pursue them even in these modern times of equality.
The myth is men "love the chase" is so far from the truth!
Most men want to be met half way. No one enjoys rejection!
The art of subtle flirting and friendly conversation have been lost.
Truth be told when it comes to both women and men there is no "one size fits all" approach to them. Some guys might feel flattered and others might be turned off or see her as being desperate or "easy".
Note: Most men and women don't see themselves as being "unique".
They really believe if you did something for them you'd do it for everyone! Very few women or men believe they are the "exception".
Real freedom is when you don't care what others think!
They either want what you do or they don't. If not? Next! :)