Ryan Dean West is Winger’s protagonist. His self-conception is dominated by several traits that drive the conflicts in the book. His young age compared to his classmates makes him feel alienated and insecure around them. He’s also a high academic achiever, which results in the age difference between him and his classmates. By endowing Ryan Dean with certain qualities that make him feel like an outsider, Smith makes him a believable and sympathetic protagonist to adolescent readers who may have similar feelings about themselves in relation to their peers. By the end of the book, Ryan Dean accepts some of these traits about himself and develops a nascent sense of self-worth.

Ryan Dean’s need to feel liked and secure about the way his peers respond to him explain why he continues the clandestine relationship with Megan, despite his feelings for Annie. Megan’s romantic approval helps him compensate for Annie’s rejections in the middle sections of the book. Up until that point, Joey’s efforts to reproach Ryan Dean about helping Megan cheat on Chas aren’t effective; Ryan Dean’s need for approval, particularly from a girl he finds attractive, overrides any ethical principle he might violate. However, after Annie accepts him as her boyfriend, Ryan Dean’s sense of self-worth is restored enough that he can stop seeing Megan.