Is our "relationship" weird or totally normal? And what should I read from it?

So there's this dude that I go to school with. He and I have some kind of weird connection. Like we have a lot of the same interests & views and when we talk it can go on and on and on.. Anyway, I like him a little bit and I think he may like me but we're both really bad at sending positive signals. Sometimes we'll both lock eyes and smile and laugh together randomly and sometimes we'll never give each other one glance. I know he likes one of the cheerleaders at our school, first it's so totally obvious and second he even told me in one of our huge conversations. Anyway, I think sometimes he gets really mad at me because I flirt with his friends. His friends are really funny and I'm not sure if I would really call it flirting I just hang out with them a lot and joke with them and laugh with them - typically more than him. He even made a reference to it once saying "When are you gonna go out with _____?" Because he thought I liked him. And I have some really good guy friends who are like brothers to me who I touch on the hands and hug and give high-fives to all the time and I always see him watch me more when I'm with them. But then when we talk we always laugh and I tend to roll my eyes and he always smiles, laughs, and keeps in the conversation. He is a really confident person [from what I can tell] and he doesn't come across nervous toward anybody. The first time we talked it was like a two-hour conversation and we just blabbered about our lives. I felt like I knew EVERYTHING about him after that and he told me all of his secrets and I felt like I knew too much, then I fell for him. Anyway, is our "relationship" has "Friends" or whatever we are weird? Or is it really normal? And What should information should I gather from it? Thanks :)