Looking at your original post, it sounds like you just want to start TALKING to him now, right? You are not planning to just walk up to the guy and ask him on a date. So I'd say, definitely initiate conversations and see how they go. If you start saying hello and chatting with each other frequently, then you'll get a better sense of whether he is attracted.
I'm with some of the others -- I like to be the one pursued. But some flirting and chatting can give the guy courage to move forward, so go for it!
I'm with some of the others -- I like to be the one pursued. But some flirting and chatting can give the guy courage to move forward, so go for it!