I wonder how many rejections a man would have to face to develop a "cockiness shield", to continue pursuing and hitting on women no matter how rejected he becomes. After all, it's a small effort for a potentially good returns.
With practice he could certainly toughen up with regard to that but I think that by doing so he would inevitably have shut out part of his heart. Getting rejected by a woman is hard for a man. H-a-r-d. It might very well be that once he successfully hits on a woman he finds interesting, he might have a hard time softening down to something resembling an emotional human being capable of falling into love and a loving relationship.
I had a landlord once who wasn't very social, and as a result wasn't very good with women (but he was a specialized mechanic and made a ton of money). Was talking to him one day, and he said that his therapist had given him an assignment to get out of his shell.
His assignment was to go to a bar (or any sort of similar place) and get rejected by ten women. That is, between that session and his next (the span of a week I believe), his goal was to get shot down by ten women in a social situation. Not necessarily crash and burn, but some kind of rejection.
After a while, you realize rejection isn't really that bad - it's the fear of rejection that's the big problem. Once you can get over that, you're going to be doing a lot better.
Since you didn't phrase this in terms of "Rejection Therapy" I have to assume it didn't pop up on your radar. It was pretty popular on here a couple of weeks ago, and Jason Shen even did a series about trying it out.
How long ago was this? The therapist was probably ahead of his time!
Actually getting rejected by women and getting blown out of "sets" on purpose is a well known PUA practice to handle fear of rejection. I remember reading about it 4 years ago or so.
I would also add that after you develop your "cockiness shield" - though a sword would be a better analogy - it needs to be maintained, kept sharp. For some reason this particular skill fades very quickly (in months) if you stop exercising it, so it's not like swimming or riding a bike.
There's another bit of bitter irony about this situation. After you become "hard" enough to attract a girl who was previously out of your league, it's not in your best interest to grow "soft" again. On the contrary, it makes the girl likely to leave you, because she didn't sign up for your weaknesses when she entered the relationship :-) Yeah, some girls will be okay with that, but in my experience they are rare.
On the other hand, going to an extreme to appear attractive can backfire. You could be stuck with your act for as long as you want to stay with that girl. Do you really want to be with a girl, no matter how attractive, who won't like the man you want to be?
With practice he could certainly toughen up with regard to that but I think that by doing so he would inevitably have shut out part of his heart. Getting rejected by a woman is hard for a man. H-a-r-d. It might very well be that once he successfully hits on a woman he finds interesting, he might have a hard time softening down to something resembling an emotional human being capable of falling into love and a loving relationship.