Winger by Andrew Smith (2013)
There is a big spoilery bit that I can't tell you but which I feel is sort of the most important part of the book and casts everything else in a slightly different light. Dancing around it makes the whole book sound light and fluffy, but don't dismiss it as such. It will totally punch you in the feelings.
There are some things I can tell you. I can definitely tell you about Ryan Dean (and Dean isn't a middle name, it's part of his first name, so he's always Ryan Dean.) His voice is earnest and self-deprecating and funny, and you can tell he's a good guy at heart. He keeps making poor decisions though, and he knows it, but he is powerless in the face of girls he thinks are hot. Somehow he makes it easy to sympathize with him even though he is doing stupid, selfish things. His story is told not just through words, but also through comics, pie charts, and graphs, which all makes him even more dorky and likeable.
He also has a great group of friends. Seanie is the guy most likely to post compromising pictures of you on the internet. JP is a good friend until he and Ryan Dean have a falling out over a girl (isn't that always the way?). Joey lives in O-Hall along with Ryan Dean and his proximity and loyalty contributes to him becoming a very close friend. He sticks up for Ryan Dean with the bullies - and Joey is gay so he is used to bullies - and also tries to steer him in the right direction when he starts making really stupid mistakes regarding Annie. There are a lot of friends and acquaintances here, and they all seem realistically different from each other, in stark contrast to the last book I read where the supporting cast were pretty much interchangeable.
The way Ryan Dean's story is told is just stream-of-consciousness enough to capture what it's like to be inside his head. For instance, he'll mention how comfortable he feels around Joey even though he's gay and then will realize how he sounds just by having articulated that, and then feels guilty about his whole internal conversation because Joey is a great guy. For better or worse, that is just how people think, and it's captured quite well here. Ryan Dean is also convinced that Mrs. Singer, who oversees the currently-empty girls' floor of O-Hall, is putting spells on him. After she threatens to suck his soul out through his eye sockets, Ryan Dean admits, "Well, to be absolutely honest, she actually just said, 'Oh, hello. It's you again,' but I wasn't about to stand there and listen to her demonic incantations." God, I love this kid.
The struggles our hero faces are much like what you'd expect from a teenager, especially one who is younger than his peers at school, but braver than he thinks. This kid doesn't shy away from trouble. He's one of the better teen characters out there, and Winger stands out even in the saturated market of young adult boarding school novels. I'm starting to think you just can't go wrong with Andrew Smith.