Well, I wouldn't call it apathy, since that would mean you wouldn't care even if you did get the girl and everything worked out great. I agree with what you're getting at, though -- the confidence can't be a sort of surface-level, fake thing. You need to be confident not because you're forcing yourself to be, but because you have a deeper inner strength that can shrug off emotional wounds and continue.
Mind you, that inner strength is by no means easy to attain. It's like physical strength -- you have to lift weights for hours every week before you get any stronger. But in the end it pays off because you can draw on it not only in matters of the opposite sex, but in all of life's other troubles as well.
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"Well, it could be worse -- it could be windy!" -popular Canadian saying.
So sayest the Writer of Silly Things!