my dating life could be a skit on prairie home companion

Insomnia has plagued me these last few nights. Last night in my restless twisting and turning, I mulled the situation with this fantastically nice man I've been out with a few times. I'm very much on the fence about this guy, and think he may feel the same about me. In fact, I think that we may be on a friend trajectory.

My concerns: he seems rather rigid (lacking that "go with the flow" thing), he may be OCD about neatness or being clean, he doesn't flirt (he may not know how), and he hasn't really laid a serious kiss on me yet so I can't get a feel for whether there could be physical chemistry.

Why I've continued to go out with him: he's cute, is the most decent and kind man I've dated in YEARS, he keeps asking me out, he's very considerate... actually he may rank in the top three for consideration. At the end of our dates we head in different directions, but this guy waits with me and chats until I get on the train, and then he takes the next train.

Tonight will be the fifth date. We're seeing a play and it is a "school night", so its not like I can ply him with mass amounts of alcohol and see if he can be uninhibited or messy... And I'll be headed out of town on Wednesday, which will sort of break the pattern we had established. Dating around the holidays is a real pain in the ass. Wish me luck.