Does he possibly want to..?

From personal experience you need to put yourself out there just once and see what happens. We only get this life one time and you will always wonder "what if" unless you swallow your fears and tell him how you feel. I lost my first love because I was afraid to put myself out there, I got a second chance and I didnt hold anything back. We arent together now but atleast I know I didnt stand in my own way.