Should I make the first move?

All this "prep"/"gangsta"/"cool" bullsh*t is starting to get to me. You define who you are! I feel sorry for the new generations - they get to miss out on being friends with people no matter what they wear and who they hang out with, GOOD cartoons and being decent human beings - but I digress. If you are into him it wouldn't hurt to talk to him. Remember, you have only one life (or so I am told). But what do I know, I'm Just A Random Guy.

First off, don't let cliques be a barrier to a potential relationship! You might be a great fit despite him not being your usual type. In your position, I would just go up and talk to him, start a conversation, flirt a little. Basically, like you say, sending him signals, showing him that you're interested. If he doesn't respond, look at the situation and see if it's because you think he doesn't like you, or because he's shy. If you think he's shy, then go right on ahead and make the first move! It's just as hard for them to make the first move as it is for us, so if he does like you, he'll definitely appreciate it!