Advice, please? (About a guy)

Wow, I'm so jumbled up it took me 6 tries to spell advice right.

So, there's this guy. (Always starts like that it seems.) Anyways, his name is Michael. He's a good friend of mine, but we haven't hung out too too much out of school. We'll talk in school sometimes though, he is in one of my classes, JROTC, and he stays after with the group a lot for things like Drill, Raiders, etc. Anyways, we're friends. The point.

I'm always afraid to talk to him. I love it once I start, but I get paranoid before I do, I can't explain it well. Like, I can't gather the courage a lot, but I normally end up having some weak conversations that I start. Normally, I have to join in on conversation to actually talk to him very well, but I don't want that all the time, I want to start something... but what? It's also like that with hanging out with him. I want to hang with him, but I feel awkward asking. I was going to go to his church last week, but couldn't--out of state, and today I didn't know details. He doesn't know my excuses, he never asked so I never told or brought it up. I want to go this Sunday though, but I don't know how to ask for details in person... I'm scared. :\

Anyways, yeah. Help prehaps? I'm not wanting a direct ticket to his heart or anything, that's impossible. I just want to get closer and earn my way up to the top, deserving it with each step. That's the way it should be, right? He's amazing, and that's what I want.

Thanks. :)