Lindsay's family and friends fear the worst when she quits the academic decathlon team and begins hanging around with a new crowd. A new friend tries to help her find her way. Meanwhile, Sam ponders asking cheerleader Cindy Sanders to the homecoming dance, while trying to cope with persistent teasing and torture at the hands of a savage bully.

Sam convinces Bill and Neal to trick-or-treat on Halloween, but they end up embarrassed while Lindsay and her friends wreak havoc in the neighborhood.

Lindsay offers to help Daniel study for an algebra test, but ends up accused by the teacher of cheating. Daniel lends sexually naive Sam a porn film.

Lindsay encourages Nick to pursue a career in music. Nick continues to practice with his current band, but quickly decides he's better than them. Lindsay encourages Nick to audition for a bigger local band. When things don't go well in the audition, Lindsay is there to comfort Nick. After learning they have to shower in gym class, Sam, Bill, and Neal refuse to do it.

Sam, Neal, and Bill befriend a pretty new transfer student, but soon fear of losing her to the popular crowd and try to win her over with a series of fun things they plan for her. Lindsay, Nick, Daniel, and Ken decide to get fake IDs so they can see a hot local band perform at a bar. However, after they go through the trouble of getting their IDs and getting into the bar, the group is stunned to find out who the hot local bands lead singer is.

Lindsay's parents forbid her from hanging out with Kim, as they see her as a bad influence. Bill grows tired of being picked last for teams for baseball in P.E. class, and not being allowed to really participate.

A car accident results in Lindsay deciding to stop hanging out with her “freak” friends. She decides to rejoin the mathletes and start hanging out with Millie again. Sam adopts a new modern hair style in the hopes of impressing Cindy. When this fails, he seeks out a new wardrobe.

When Bill talks about being allergic to peanuts in class, Alan tries to prove he's lying but Bill ends up in the hospital after an allergic reaction. Lindsay smokes weed for the first time.

Lindsay tries to convince Harold to let her join her friends at a Who concert. Kim and Lindsay accidentally run over Millie's dog. Kim starts hanging out with Millie. Lindsay wants to tell Millie the truth about her dog, but Kim doesn't. Meanwhile, Nick teaches himself to play guitar and writes a love ballad for Lindsay and decides to play it for her despite Kens' objections. Ms. Haverchuck stuns Bill with the news that she has been dating Coach Fredricks.