Most Helpful Guy
I think he was just trying to show off and/or trying to convince himself that he is cool now. Probably the former. If this was a conversation between just you and him I think he's trying to impress you.
Most Helpful Girl
I'd say you don't relay only on words. You see he is sort of shy, but he says he isn't. Now he says he would approach if he was interested. You'll see if that is true by his actions. I wouldn't bet on it.