Guys! what does this mean... is he dropping hints?

Come on, you're really thinking this hard about it? Obviously the guy is into you. He's just being extremely shy and afraid about directly asking you if you have a boyfriend or not, for the fear that you will come back with the direct answer of know. By bringing it into the conversation and having you casually answer yes or no, is the easiest way for him to find out. And by telling you he's going to have another "girlfriendless" semester is telling you flat out, "I DO NOT HAVE A GIRLFRIEND, I WOULD LOVE TO HAVE A GIRLFRIEND, I WOULD LOVE IT IF YOU WERE MY GIRLFRIEND." Trust me on this, I'm a 20 year old guy in college, I have a little wisdom in this department. If you like this guy a lot to, you need to be the one to say something, because obviously he is too afraid to. There's nothing that turns a guy on more and makes him feel better than when a girl tells him she likes him and asks him out instead of the other way around. Take the initiative, you won't regret it.