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Cher enrolls into drama class and meets a handsome guy named Donal. They then set a date at a late-night Jazz club, despite Mel giving Cher a strict curfew.
During a class presentation, Mrs. Geist-Hall falls over a backpack and gets hurt. Principal The principal forbids the students from now on to carry backpacks. Cher and Dionne do not accept this ban and organize a protest.
Bronson Alcott High School receives a new principal, who forbids cell phones and institutes other strict rules. When Mr. Hall is fired, Cher decides to act.
Cher finds herself partnered with the school genius/total geek, Felice Lesser. Despite coming from different social circles, Cher is shocked to discover that she genuinely likes Felice, and must decide whether to keep being friends with her once the project is over, despite what it could mean for her social standing at Bronson Alcott High.
Murray and Sean are having a new passion – golf - with Dionne feeling neglected. She then seeks advice from Cher, who suddenly teams up with Dionne against Murray and Sean in a "Battle of the Sexes" golf game.
This is the only season to feature Twink Caplan, David Lascher, Michael Lerner and Wallace Shawn as Mrs. Geist-Hall, Josh Lucas, Mel Horowitz and Mr. Hall.