WINGER is exactly the sort of book I love to pick up. Contemporary, young adult, and very long. One of my favorite books from last year was THE MISEDUCATION OF CAMERON POST because the length allowed me to get totally invested in the characters and the story, all while not wanting the story to end even though the book was very long. 
 Ryan Dean West (Winger) is away at a boarding school. He is several years younger than the rest of the kids in his class, and on top of that he got in trouble last year and so this year has to live in Opportunity Hall with the rest of the troublemakers (and this year it's all guys; the girl's floor is empty). 
 His nickname is Winger because of his position on the rugby team, the place where he excels. Where he doesn't excel is with his best friend Annie and romance - he is very much in love with her, but has a hard time getting past her comments that imply he's younger and a brother type. 
 Winger has a very humorous personality, and throws in drawings from time to time throughout the book. He doesn't take himself too seriously most of the time, and Andrew Smith has pinned his personality down to the letter. One of my favorite Winger quirks is that he doesn't curse in real life, but will often add in cuss words as he's retelling the story, only to remind us that he didn't actually say it that way. 
 There was a very serious event towards the end which I was not expecting at all, which ended up tying the book together as a complete story in a way which I could not have predicted. 
 I highly recommend WINGER. This is a perfect book if you're going on a road trip or somewhere where you want to become fully invested in a long story.