I would search for a way to handle a rejection in stead of trying to be numb for rejection.
And it is a self esteem issue.
If it was not, you would n't care about rejection, because you know who you are.
I think that a "stunning" girl is more impressed by someone who is "himself", vulnerable, open and honest, having the bravery to show just who he is. Rather than somebody who is "extremely extrovert" just trying to "get" her.