One thing that's holding a lot of guys back from approaching/asking women out is the possibility of rejection. The mind-blowing thing is that in trying to avoid rejection, they freely choose the one thing that is even worse, to not even try.

If you don't put yourself out there, you won't get rejected, but you'll never be succesful either. Sure, rejection stings for a while, but not trying stings forever. A no will allow you to move on, a 'what if' will haunt you for a long time.