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Have you ever had that feeling that a guy likes you when maybe he doesn't?

So, there's this guy in my P. E. class and you know he always listens to his music- he's kind of in his own little world.
You see, I think he's just trying to act all cool and kind of wants to be one of those wanna be popular sorta person. But hey I've never met him so I can't tell.
Strangely enough, he complimented my dog- he was talking to my mom. I don't think he even knew that she was my mom, she doesn't come often near the school.
He has embarrassed himself several times though (like me in front of him) and sometimes he walks around by himself wearing his 'totally cool looking clothes'. He doesn't even look at me in P. E. (when I glance at him casually). And the funny thing is he's kind of cute but I don't know what his personality is like, so it's hard to say that I know who he is personally. And I'm new to the school, by the way, and I have only a few new friends.

Back to my story, just earlier today I had left early before the bell rang to end lunch so I could get to my class on time. As I was walking up a flight of stairs, wearing a brown dress (so I could look like a peasant, for medieval day. Which by the way is the first time I have worn a dress to school.), I heard footsteps behind me and out of the corner of my eye I see blond hair and a flash of his face. I kept walking and then I heard "What's up?" although it wasn't his voice but the person beside him saying. He shushed her or kind of made an annoyed noise as I continued walking. For some reason I think it was directed towards me and the girl was poking fun at him or trying to capture my attention.
I keep thinking about it and tossing it over and over in my head but I still can't seem to figure out any signs that he has liked me before. If you need extra info, just let me know.

What do you think? And how can I relax around him when I feel he may like me?
Should I try going after him?