Talk to your friends about this guy you like, his friends if you know them, and find out things you have in common. Find some places and times you can be alone together to talk, sounds like you already have...low pressure just hanging out. After you're already talking about small stuff and things you both like, tell him you like being with him, talking to him, things you like about him...flirt a little and make sure you are going to hang out or meet at school functions...setting up another low pressure date.
If he doesn't ask you out after knowing him better, then you may have to do it yourself ...but chances are if you show him you like being with him alone he will see you are interested and you'll know if it will work making it romantic and more than friends. Just make it clear if he doesn't take the hint if he seems shy. He's going to be flattered by that even if he's not interested and now you at least know what's going on. There's nothing wrong at all with giving him advice and being his friend, then asking him out...I hope it works for you.