Winger by Andrew Smith

Ryan Dean West is a fourteen-year-old junior at a boarding school for rich kids in the Pacific Northwest. He’s living in Opportunity Hall, the dorm for troublemakers, and rooming with the biggest bully on the rugby team. And he’s madly in love with his best friend Annie.

With the help of his sense of humor, rugby buddies, and his penchant for doodling comics, Ryan Dean manages to survive life’s complications and even find some happiness along the way. But when the unthinkable happens, he has to figure out how to hold on to what’s important, even when it feels like everything has fallen apart.