Clueless

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 Dionne 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 they have not been linked by marriage for more than five years, Mel replies he divorced his wife, not his stepson. Cher playfully mocks Josh's idealism while Josh teases Cher for her vanity, superficiality, and selfishness.
Initially receiving poor grades on her report card, Cher renegotiates her grades with her more lenient teachers but cannot budge the hard-grading Mr. Hall. To soften him up, Cher orchestrates a romance between Mr. Hall and awkward teacher Miss Geist. As a result, he 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 he is prouder of her negotiation skills than if she had earned her grades.
When "clueless" transfer student Tai Frasier arrives at the school, Cher turns her into her next project. Cher and Dionne give Tai a makeover, providing their 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 Tai and the “unworthy” Travis. Instead, Cher steers Tai toward 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 Cher 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 Cher’s attempts at mentoring Tai and volunteering for charities, Josh realizes that despite her superficiality, she is sincere.
Fashion-conscious metrosexual Christian Stovitz, a handsome new student, immediately attracts Cher's attention, becoming her target for a boyfriend. When Cher goes to a party with Christian, Josh becomes protective, also attending the party. 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. Christian deflects her advances and is distracted admiring the male actors in the film. After Murray informs Cher and Dionne that Christian is gay, Cher decides to remain friends with Christian, approving 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, asking Cher's help in pursuing him. Jealous, though oblivious, Cher tells Tai that she is not right for Josh, and 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 helps with 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 Josh, Cher finally realizes that she is in love with him. 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 she and Josh embrace and kiss.