| Director | Amy Heckerling |
|---|---|
| Budget | $12 million |
| Box office | $88 million |
Cher Horowitz, a stylish, popular, and good-natured teenager, lives in a Beverly Hills mansion with her wealthy father, Mel, a gruff litigator; her mother died during a liposuction procedure when Cher was a baby. She attends Bronson Alcott High School with her best friend Dionne Davenport, also stylish and from a wealthy family. Dionne has a long-term relationship with popular student Murray Duvall, though Cher believes she should be dating more mature men.
Josh Lucas, the socially conscious son of Mel's ex-wife from a brief marriage, visits Cher and her father during a break from college. When Cher points out that they have not been linked by marriage for more than five years, Mel replies that he divorced his wife, not his stepson. Cher playfully mocks Josh's idealism while Josh teases her for her vanity, superficiality, and selfishness.
Initially receiving poor grades on her report card, Cher renegotiates those with her more lenient teachers but cannot budge the hard-grading Mr. Hall. To soften him up, she orchestrates a romance between him and the awkward teacher Miss Geist. As a result, Hall relaxes his standards, allowing Cher to renegotiate the grade. After seeing the teachers' newfound happiness, she becomes enthusiastic about doing good deeds. Cher's father professes that he is prouder of her negotiation skills than if she had actually earned her grades.
When a "clueless" transfer student named Tai Frasier arrives at the school, Cher turns her into her next project. She and Dionne give her a makeover, providing her protégé newfound confidence and style. When an amiable but clumsy skateboarding slacker, Travis Birkenstock, becomes smitten with Tai, who reciprocates, the social-status-conscious Cher tries to extinguish the attraction between them, seeing him as "unworthy". Instead, she steers her towards handsome, popular student Elton Tiscia. However, Elton has no interest in Tai and is instead interested in Cher, whom he tries to kiss in his car after a party in Sun Valley. When she rebuffs him, he leaves her in a parking lot out of spite, and she is mugged at gunpoint. With no money, Cher's only choice is to call Josh to pick her up. Seeing her attempts at mentoring Tai and volunteering for charities, Josh realizes that despite her superficiality, Cher is sincere.
Christian Stovitz, a handsome metrosexual new student, immediately attracts Cher's attention, becoming her target for a boyfriend. When Cher goes to a party with him, Josh becomes protective, also attending the party in the process. There, he gallantly rescues Tai when no one asks her to dance. Later inviting Christian to hang out watching a film at her home, Cher tries to seduce him. However, he is distracted admiring the male actors in the film and deflects her advances. After Murray informs Cher and Dionne that Christian is gay, she decides to remain friends with him, approving of his taste in art and fashion.
Cher's privileged life takes a negative turn when Tai's newfound popularity strains their relationship. Additionally, when Cher fails her driving test, for the first time she cannot negotiate to change the result. Her mood worsens when Tai confesses her feelings for Josh to Cher, asking Cher's help in pursuing Josh. Jealous, though oblivious, Cher tells Tai that she is not right for Josh, so the two girls fall out.
Feeling "totally clueless", Cher reflects on her priorities and repeated failures to understand or appreciate the people in her life. She begins to help by performing document review on her father's legal case along with Josh, and they begin to bond. Pondering why she is bothered by Tai's romantic interest in him, Cher finally realizes that she is in love with Josh. After her epiphany, Cher begins making awkward but sincere efforts to live a more purposeful life. This includes captaining the school's Pismo Beach disaster relief effort. She accepts an invitation from Travis to a skating tournament in Long Beach, where she reconciles with Tai, who is now dating Travis.
Cher and Josh eventually realize their feelings for one another, culminating in a kiss. Some time later, Cher attends the wedding of Mr. Hall and Miss Geist, which she and Josh attend as a couple, along with Dionne, Murray, Tai, and Travis. Cher catches the wedding bouquet and kisses Josh.