Cher Horowitz lives in a Beverly Hills mansion with her wealthy father Mel, a gruff litigator; her mother died during a liposuction procedure when she was a baby. Cher is attractive, stylish, good-natured and popular. She attends Bronson Alcott High School with her best friend Dionne Davenport, who is also wealthy and beautiful. Dionne has a long-term relationship with popular student Murray Duvall. Cher claims that this is a pointless endeavor for Dionne.
Josh, Cher's socially conscious ex-stepbrother, visits her during a break from college. They spar continually but playfully. She mocks his idealism, while he teases her for being selfish, vain and superficial, saying that her only direction in life is "toward the mall".
After receiving a poor grade, Cher decides to play matchmaker for two hard-grading teachers at her school, Mr. Hall and Miss Geist. She orchestrates a romance between the two teachers to make them relax their grading standards so she can renegotiate a bad grade on her report card. After seeing their newfound happiness, Cher realizes that she enjoys doing good deeds. She then decides to give back to the community by "adopting" a "tragically unhip" new girl at school, Tai Frasier.
