Set in the prestigious boarding school, Pine Mountain, Oregon, the story follows fourteen-year-old Ryan Dean West as he recounts past events that he has experienced in his journey of maturation.

The narrator, Ryan Dean West is a fourteen-year-old junior at a boarding school for rich kids.

After being invited to play a poker game by Chas, Ryan Dean's former roommates JP and Seanie warn him that losing will bring a penalty.

He apologizes and they meet at Stonehenge, a circle of stones in a clearing of the forest with which Annie believes you can make a wish whenever going in.

Annie shows Ryan Dean a painting on the wall she had found of two overlapping circles and the word "someday," which reminded her of the wish he had made at Stonehenge.

At midnight, Ryan Dean plays his second round of poker with Chas, Joey, Kevin, and Casey, and the boys take shots of whiskey.

Casey assigns the boys the task of driving to buy costumes for all five of the players, so Joey decides to be the designated driver since Ryan and Chas are both drunk.

On his way back to his room, Ryan Dean runs into Casey and Nick, who accuse him of being gay and make him aware of how much they'd like to fight him.

Ryan then sees an upset Joey who announced in front of other people that Casey needed to hit on another gay student at Pine Mountain.

Ryan Dean returns to a dark and eerie dormitory where he encounters a drunken Casey threatening to kill him.

Ryan Dean notes that he stopped talking after Joey's death, with the exception of whispering to Annie when he needed to.

Chas Becker (Betch)- A senior at Pine Mountain, and Ryan Dean's roommate in O-Hall.

Sean Flaherty (Seanie)- One of Ryan Dean's former roommates for his first two years at Pine Mountain, and rugby teammate.

Because of Ryan's Dean's passion for drawing, he inserts a collection of comics into each chapter, visualizing various events that he previously experienced.

These comics correlate to the visual Venn diagrams that Ryan Dean uses in order to tell elements of his story more clearly.

Smith makes readers aware of the disconnection between men and women through Ryan Dean's relationship with Annie, Megan, and his own mother, and how this differs greatly with his ability to easily understand all of his male friends on his rugby team.

Since Ryan Dean is only fourteen-years-old in a class of students two years older than himself, he struggles with emerging from a little boy into a man, so he is easily influenced by the male characters in the novel and continuously attempts to identify with them so as to fit in.