Saluting with misty eyes
Act casual about the whole thing, and don't place the importance of your whole life on it. During the course of conversation, say something like, "How about we go see (Kill Bill II, Ella Enchanted, whatever). I was going to go this weekend, and figured it would be cool to have the company." Or while you are talking, make a comment about going to McDonalds, or Pizza Hut, or some such... just make it seem like it is a last minute thing that you JUST thought of. That way, there is no pressure, and if he says no, then it isn't a rebuke of YOU, just your offer. If the topic doesn't come up during the "date" then make a second date, and eventually, it will happen.
just my thoughts, though.
Some people are like Slinkies . . . not really good for anything, but you still can't help but smile when you see one tumble down the stairs...