Ryan Dean West is in over his head. He is a fourteen year old junior at Pine Mountain, a boarding school for wealthy kids, and he feels like a little kid even with his friends. Worse, he has a huge crush on his friend Annie and she seems to only think of him as cute and as a friend. Worse yet, his roommate in the dormitory is Chas Becker, a not-too-bright and very scary member of the rugby team. Despite his small size compared to those juniors who are actually old enough to be juniors, Ryan Dean is also a member of the rugby team because of his speed.
Between rugby, tensions with Annie, and another girl at Pine Mountain who develops a thing for Ryan Dean, it would seem like Andrew Smith’s Winger would be action packed. Instead, the book is more of a character study driven by the strong voice Smith gives Ryan Dean. He is a flawed but likeable character who encompasses the sometimes impulsive, sometimes passive and always turbulent years of adolescence.