I'd like to be more than friends with this guy, but I don't know where to start, can anyone help?

So I have been out of a relationship for a few months since the guy turned out to be a real dirtbag. I was a little emotionally distraught for a little while, but I'm doing much better now and there is this one guy who I would really like to spend more time with. I've known him for years and he's a real sweetheart, but he's not the type who easily gets into relationships. We've always kind of flirted a little bit with each other, but never really gotten together, since we are teammates and relationships on the team could cause problems. Plus we are both a little more timid and on the quiet side. But I've always loved him and his personality, and I want to see if we could start a relationship before the summer is over. I think it might be difficult though, because he is younger than me and not particularly open about how he feels in some situations, and I don't want to make him uncomfortable. What could I do to maybe get something more started between us?