How can one overcome their shyness?

Don't worry about being shy, because "shy" is refreshing in this day and age. There are more people out there that are shy than not. It's best if you let him tell you how he feels and he'll probably do this as your relationship goes on. If you aren't dating then it's OK to ask him out, but before you do, be sure you are mentally ready for rejection. None of us like rejection, but all of us have experienced it. Being attracted to someone is all about chemistry and it either mixes or it doesn't. Don't risk a good relationship because you are afraid of being rejected. It's not personal. I'd rather someone be honest with me than take me for a ride I don't want to be on. So, take a deep breath, and do something about this. Don't tell him you like him, just take it slow and easy and let him make the first move. Body language says it all. Good luck Marcy