Is This Going Anywhere

My advice is to take things slow - start off as friends, and usually the good friendships can make the best long lasting relationships :) Do some fun things together - go to the library, the zoo, bowling, out for coffee etc. etc. These aren't "dates" per se, but they kind of are - at the very least you will both have a fun time :) In general, I think it's better to let the other person make the first move or say something about it (or sometimes things will just sort of happen, lol...) - otherwise you bring up an awkwardness if the other person is not receptive. But if it is driving you crazy and you are falling for him, then you could maybe try hinting at it at first to see how he reacts to it (I don't really know what to hint at - but something like "do you think you'll start dating anyone again soon?" or that kind of thing might give you an idea, but you have to be able to talk about that kind of stuff without it getting weird) If he's receptive then chances are you'll both start dating without really knowing it - all of my relationships have just sort of "fallen" into place with guy friends of mine. Anyways, don't put too much thought into it or you will drive yourself crazy, go with the flow and be relaxed - it's better to take it slow but go for a relationship than let it slip out of your hands and regret missing the opportunity later down the road (though some people I believe are truly meant for each other and will end up gravitating towards each other again even if they do not get together earlier)...