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Dean Winchester is no stranger to fear. He's faced down demons, monsters, and even Death himself. But when it comes to kissing Castiel, he's scared out of his mind.
It's not that he doesn't want to kiss his best friend and maybe more than a friend. It's just that he's never been good at expressing his feelings, especially when it comes to something as intimate as a kiss.
What if he messes it up? What if Castiel doesn't want to kiss him back? Dean just doesn't know if he can handle the rejection.
So instead of taking the plunge, Dean chickens out every time the opportunity presents itself. It's not the most heroic thing he's ever done, but it's the only thing he can do to keep himself from getting hurt.
Dean finally summoned up the courage to kiss Castiel. It was everything he'd ever hoped for and more.