The famous thing called fear. THe only thing that is stronger than hope. Many people have had their fights against it. Some won, and some lost.
The ones that won were brave, because even when they lost, they kept trying it. The ones that lost never won, simply because they already gave up before the fight. So tl;dr I dont want to say YOLOOOO, but it seems valid. Just go for it and kick some balls bro, because if you don't try you always get rejected. And when you get ditched, you'll think after; YEAH I DID IT. SHE REJECTED ME, I DONT CARE. HER FAULT, NOT MINE. I WILL GET ANOTHER CUTE GIRL SOON. Otherwise you'll keep playing those scenarios in your head; what would have happened etc.
Good luck man!