Any reason to flirt at all?

ok well do you want to become friends or go out with him? if you wanna go out with him forget the 'become his friend' part.

Start talking to him, about sport, school, his hobbies watever, don't forget to say some things about yourself as well if you want him to do all the talking then it's not gunna work out. once he stops being shy and looking uncomfortable around you move things up to the flirting, tease him abit (lighty or as a joke), bump his hip if your close, make physical contact, be careful with hand holding, he might get abhead of himself, curl upto him if it's cold and sit next to him at lunch that sorta thing, eventually things will move foward and you two should start dating.

hope that helps

I am kind of shy myself(im gettin better) but when I was REALLY shy as this guy your describing sounds like the best thing a girl can do to get to know him is to just talk with em. Shy guys are usually always waiting for the other to come up to them and talk with them. Who cares if it seems awkward, it will probably be awkward for him too! Be yourself, ask truthful questions that you actually want to know the answer to. Ask questions that start conversations instead of asking 50 questions that can be answered with yes/no. Remember, the one you love won't always find you, you have to do work too. My 2 cents! Hope I helped.