Using women as a prop for self confidence is pretty douchey.
What he's really doing is using interaction with women as practice to be better at interaction with women.
I'm not really sure how else he should do it.
Maybe he could have established friendships with them, and "used" them even further?
Specifically, by learning to not care about the women in question or the interactions.
This is why comparing talking to people with shooting freethrows is goddamn weird. People are not basketball rims. The basketball rim lacks subjective experience.
e: The reliable indicator that you're weirding out some random woman is that you're not in a single's bar and acting like your trying to have sex with her.
Well, at least some fear of rejection is fuelled by caring too much. 'If I ask her out and she says no then she'll hate me and they'll hate me and I'll hate me and I'll want to die and I'll curl up into a ball and retreat from the world and die!'
Sometimes one does have to learn to care a little bit less, in order to get the chance start to learn how to genuinely care for the real person, not the made-up person in one's mind.