CB1....lets turn the question around. Would you date a girl that wore a hair system? (That’s not a proposition, its just a question to get you thinking...)

Honestly, I think it all depends on the woman. Some women will run a mile, whilst others will be really supportive and caring. You just have to learn to be comfortable with yourself. If a girl rejects you because of your hair, then she's probably not the right one for you.
I personally don't mind dating bold men, as long as they can hold themselves with confidence and have the personality traits I look for in a man. I haven't dated a man that wears a hair system (very ironic) but I don't think I would have a problem with it.

CB1 just be confident with yourself, have some ambitions and goals and go out and achieve them! Girls will flock after a "go getter" whether bold or not. As for the girls that reject you, their loss!

Best Wishes!