I was in a similar situation this past Winter. This friend of mine and I decided to get involved (physically) and before doing so we set some ground rules. One of the things we decided on is that we would like to be together (as a couple) but the timing is off (he's away at school and I'm here at home). So having that initial conversation made our ability to jump from "hook-up" to "relationship". We're still talking and things are fine. I don't want to jinx it so I won't say much more other than I enjoy his company when he's around and I have feelings for him. But all he knows is that we aren't going to worry about things...for now.
So you can do the adult thing and just bring it up, or ride it out and see what sort of signs he gives you. Often it depends on how well you know the person. In my case the guy is a friend and has been one for some time now.
Best of luck! I hope that things work out for you - it'd really be nice to have a Valentine huh!!??
