In regard to taking a chance on ourselves, most of our fears essentially boil down to being afraid of failing in public. And there is some validity here. I don't think we should do away with this fear entirely, pretending for even a moment that we could.
If my dream were a woman, would she be into me? Would she find me attractive? Or would I come off as some clingy, cloying loser, desperately trying to get her attention by any means possible?