I am of a mind that dating a housemate is asking for trouble. First of all, the fact that you live with them makes it sound more serious than it may be at the beginning. Also, if things go bad and you still have to live together, things can get awkward.
When I moved in with my housemate last month, we were 100% just friends. I never would have looked to find a house together if I had suspected we'd be anything more than that. But things have changed in the past few weeks, and I think I may be falling for him, and I have fairly good evidence that he feels the same about me. What do you all think about the prospect of dating a housemate? Terrible idea? OK idea? I'd love a bit of outside input from your collected wisdom. Details on my particular situation can be found on my blog of course, if that may help inform your advice.
It's one of those tricky things because living together might create the illusion that the feelings are deeper than they actually are. That happens when you're constantly in the same vicinity of someone else and you spend time together, especially when you find each other attractive.
I can't really say you should or shouldn't date a housemate because every situation is different. It could be real. It would help to be honest about it, with yourself (as you're obviously doing) and with him. But just be aware that sometimes living arrangements can cloud judgment. I did have a housemate once that I really started digging. But then I met someone else and realized I was only interested in the housemate because she was there, filling that void for the time being.
Be honest with him. Discuss ALL the what ifs. It doesn't necessarily means trouble or drama, but if you keep acting like a girl with a high school crush, than it's bound to end bad.