When RJ's shorts fall off in front of the whole school, his life is turned upside-down.

RJ tries out for the school musical to get closer to Jenny Swanson.

When RJ begins working to save money for a gift for Jenny Swanson's Sweet 16 birthday party, he soon learns his new employer has a strong sexual appetite, and Miles searches for a new best friend to replace RJ, due to his busy work schedule. At the end of the episode, RJ and Miles are best friends again.

When Jenny becomes single, she asks RJ to study with her.

RJ becomes interested in a new girl at school and discovers that she is a member of the Purity Club.

RJ lies to the jocks about his progress with Claire; Miles is busted for spreading rumors.

RJ's parents go away for the weekend, leaving him in the care of a sexy babysitter; Miles throws a party for the nerds.

While in detention, RJ befriends a tough thug; Lily tries out for the cheerleading squad.

Unable to concentrate on his tutoring with Jenny, RJ fears that he's losing his focus and failing both himself and the girl of his dreams, so he and Miles conspire to steal a cheat sheet from a teacher's house. Unfortunaley, Miles makes the mistake of getting his psychopathic Iraq War Vet brother involved, and promising the answers for other jocks at Pinkerton High.

Lily's dreams might actually come true when RJ somewhat reluctantly decides to ask her to the upcoming dance. Things get a little sticky, however, when Miles raises the bar with an unlikely date and RJ finds himself in a tough spot.

RJ and date Jenny try their hardest to have the "best winter formal ever," but RJ's guilt over leaving Lily lands him back at her hospital bedside, where the two keep their promise to lose their virginity together.