What are some signs that a shy guy is interested in you? Advice appreciated!?

By your explanation on things, it looks like he's interested but not sure how to approach you. The best thing to do is be patient as the response before. You don't want to throw yourself at him because you'll really catch him off guard. Just play your role and keep sending little hints. He's probably afraid to lose his bad boy image but if he really likes you, then he'll make the approach.