I don't know if he likes me or if I like him, help!

If he is making the effort to talk to you, odds are he likes you at least a little bit. And if this is every night for that long, I'd say it is a considerable amount.

It sounds to me that you do like him. You're spending a lot of time talking to him and kind of bragging about how cool he is to us. (:

My experience is that guys don't spend free time talking to girls that they don't like.

Well for starters, build your confidence more. You said that you're sure that you're a loser at your school and if that's what you think about yourself then you need to work on yourself before you get involved in a relationship.

If you want to know how he feels about you just ask him. Get THE bottom line of how he feels towards you. I think that he does if he's calling you every night and you talk for hours. Just don't depend on him to make you feel better about yourself because if you two were to go out and then break up that will lead to some serious emotional scarring.
So basically, once you're secure in how you feel about yourself then go after the guy. He sounds great because of the ways that he's showing how he cares about you but at this point in your life you've got to be focusing on who you are rather than some guy that won't matter 20 years from now.