He's so cute but shy...

Ok when it comes to the shy guy you could do this. Double date, like you and he could hang out and your with a friend whose dating the othe person. This way it's not a group of friends and your attention could be taken by another guy who wants it. You can talk to the shy guy while your friends talk to each other but yall are still just hanging out, see? Talk to him, he won't break his shyness if he hasn't done it now, it's soemthing he has to grow out of. You can help him,he's probably unsure what to do or say and kicks himself as he passes you by without saying a word. If you take the initiative it might work out for the best.

Go to the mall and talk with him, go play the arcade, it's small stuff to draw him out. He might do just fine once he's out of school. I was like that. It was not a comfort area for me. When I got to the mall or music stores it was easier to talk to anyone. Get to know him and find his interests. If things go good, you can also just drop a line to let him know hey that was fun I'd like to do it agian,but this time YOU(shy guy) pick the place. That way he can take the next step and he knows your interested. Best of luck

Just casually ask him to hang out with you. Doesn't even have to be any place romantic like a sit-in dinner. Could be something like a movie or even at an arcade. Your goal here is for both of you to get to know each other but in a light-hearted kind of way. There's plenty of time ahead to take things seriously.