RJ feels confused over what happend at the hospital and his feelings for Jenny.
In an attempt to win over the girl of his dreams, RJ asks Jenny on a date. When she says "yes", he and Miles prepare with a G-T-L makeover from Cousin Vinny .
Lacking privacy at home, RJ takes Jenny to the school lock-in to get a private evening together. Miles hands out biscottis to the students at the lock-in, unaware of what they contain. Lily decides to ruin RJ's and Jenny's night.
Jenny is stressed out because she has a bad case of acne, which puts a strain on her relationship with RJ. Lily receives her settlement money from the accident. This makes her suddenly popular, and a part of the in-crowd. She learns soon though that a place in the spotlight has its price, and decides to help Jenny who has been ostracised from the group of popular girls.
RJ's grade starts to suffer due to his life crumbling around him. Jenny tries to tell RJ that her parents are out of town for the weekend and says that she wants to lose her virginity then. Meanwhile, Miles gets into trouble with the hot substitute math teacher and has to stay after class.
RJ and his tutor Amy decide to help RJ's father to clean up and get a job, but with unexpected results. Miles and Lily take part in a peer support group at school. Jenny and RJ make decisions about their relationship.
RJ wants to take his tutor Amy to a Weezer concert, but being underaged poses a problem. Miles wants to go to the concert because he wants to meet Weezer's groupies. At the same time coach Sinclair has started dating RJ's mother.
RJ's separated parents both invite him to keep them company on their would be 20th anniversary, leaving RJ to choose between them. Meanwhile Miles joins the cheerleading squad in the hopes of meeting some chicks.
RJ asks his dad for driving lessons as his 16th birthday approaches, but he gets more than he bargained for when his dad brings him to Hunkeez, a male strip club.
RJ throws a "Max Bash" to get back at Max Owens for ruining his birthday, and things quickly get out of hand when Max and his jock friends show up at the party.
RJ and Jenny get nominated for Mr. and Ms. Pinkerton right as he's ready to take his relationship with Amy to the next level.
RJ and Max Owens battle for the title of Mr. Pinkerton. Meanwhile, RJ's relationship with Amy hangs in the balance.