Have you ever outgrown something? In Looking for Alaska by John Green, Miles feels that he's outgrown his school, he wants to go somewhere new. So he goes to a new boarding school looking for something new. But I think secretly he just can't find where to fit in. It's like trying on new clothes. He just can't find anything in his size.
Miles didn't have a lot of friends in his old school. I think he couldn't really find his own group of friends so he wanted to go to a new school so he could find somewhere to belong. Miles doesn't have a big social group may never will but he wants to find new friends and new adventures. Also he has a love of biographies of famous people. I think that symbolizes that he seems to connect to people in books rather than people in real life.
I think the author is trying to say that we have all have own different friends that we can connect with. That we all now our limitations friend wise and that sometimes we need to step out of the boundaries, thats what making new friends is. Stepping out of out friend boundaries.
I feel this is kind of like Happy face in which happy face wanted to start over and just completely make a new life for himself. Except miles just wants to meet to people. He wants to out grow his old clothes and try on some new ones. Some might be too big but, hey, we all grow into big clothes don't we?
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