literally, what you'll learn is that if you don't ask a girl out (or similar), shy or not, because of fear, you'll never be successful with them. you'll never get laid. you'll never get where you want to get to. if they say no/reject your advances, all they can really say is "no", and they're not petty enough to do anything worse than this (in fact, why wouldn't a girl be *flattered* that a guy has asked them out or similar?). it doesn't matter about the timing - if they like you, they'll say yes. there are billions of girls in the world, and if one out of a billion says no to you, then who cares? it will sting, sure, and it will sting every man if they are rejected by a girl they like, but you have to get used to it. you have to raise your confidence levels to heroic proportions. you have to become that legend who has that impenetrable warrior ego/bravery that women are attracted to (I'm not necessarily talking about cockiness). you have to sacrifice your short term comfort for your long term interests. even if you get rejected a thousand times, you just have to keep letting yourself know that it's not you, it's them - the fact that they're not attracted to you does not mean you're objectively not good enough for girls - you just haven't found the girl that *is* attracted to you yet. girls are *very* fussy with who they like, unlike most guys. the first time getting rejected is always the worst, and I'm talking about getting rejected in real life, in person. but you just have to get over that first hurdle. you have to see that first rejection opportunity as a benefit to your life - because once you've experienced it, you'll know that you can take it and you can take it again with the chance of getting a "yes" from them later. there's never going to be a "yes" without a potential (probable) no many times down the line. ask any romantically/sexually successful man.
TL;DR - refer to swole's message