Darn it, it might have moved to " buddy territory". I am sorry, it happens a lot. I find that most guys generally start hanging out with a girl because they are attracted somewhat, but if for whatever reason that attraction does not lead to anything, you quickly move to " cool girl" territory. I am not sure if that means he is not serious or whatever, not to me, but you know him best.
I am just going to bring up something that Jenava said a while back, when you had that wine party. From your behavior around him, she told you she did not even notice that you liked him. Perhaps he did not get any clues. It's okay to show interest. I dunno. perhaps you could be more overt, perhaps it is not even worth it. I dunno.
Ack, I had lots of hope for this guy... I'm sorry.