Cher Horowitz (Alicia Silverstone) is a wealthy, popular 15-year-old living in Beverly Hills with her widowed father, Mel (Dan Hedaya), a successful lawyer. Though good-natured, Cher is naive and caught up in a superficial lifestyle revolving around expensive clothes and the social hierarchy of her high school. Her best friend Dionne (Stacey Dash) has a similar outlook on life, though she dates a high school boy named Murray (Donald Fasion), which Cher claims is a pointless endeavor. Cher's debate teacher, Mr. Hall (Wallace Shawn), gives her a C grade for the semester, which starts a dramatic chain of events. Dionne, who got a lackluster grade as well, hatches a plan with Cher to find a romantic interest for Mr. Hall, thus hypothetically making him happy enough to consider boosting their grades. They select another teacher, Miss Geist (Twink Caplan), as the chief candidate, and spark a mutual interest between her and Mr. Hall with a forged love letter and some subtle manipulation. The teachers soon become a couple, and both become much more lenient with their grading. Cher works her grade up to an A minus, greatly impressing her father. At home, Cher interacts with Josh (Paul Rudd), the college-age son of one of Mel's ex-wives, who often stays at the Horowitz home to avoid his mother and new stepfather. Josh is nearly the polar opposite of Cher: an earthy environmentalist with an interest in societal welfare. The two have a generally amiable but lightly contentious relationship, with Cher teasing Josh about his alternative lifestyle and Josh criticizing Cher's materialism. Mel openly approves of Josh's self-assurance and focus, encouraging Cher to find similar direction in her life. Tai Frasier (Brittany Murphy), a grungy artist with a trusting disposition and a clueless grasp of high school popularity, transfers to Cher's school. Cher and Dionne befriend Tai, and decide to give her a makeover to improve her social standing. However, Tai sparks up a romance with cheerful skateboarding stoner Travis Birkenstock (Breckin Meyer). Cher, fearing for Tai's reputation, attempts to steer her toward the rich, popular, newly-single Elton (Jeremy Sisto). Cher leads Tai in after-school workout sessions, guides her in cultivating a new wardrobe, and expands her lexicon with trendy vocabulary. Josh disapproves of Cher's project with Tai, accusing her of attempting to turn an innocent girl into a superficial brat, but Cher maintains that she is doing Tai a kindness. Through a series of orchestrated interactions, Cher gets Tai and Elton to notice each other. Tai is giddy with excitement, and while Elton is surprisingly receptive, he pays much more direct attention to Cher. To present the newly made-over Tai to the high school elite, Cher and Dionne bring her to a party. Once again, they attempt to steer her toward Elton, and believe that they made a connection when Tai is knocked unconscious with a projectile shoe, and Elton revives her with an ice pack. However, when departing, Cher winds up being driven home by Elton, who makes a pass at her, confirming that he had never been interested in Tai. Cher is shocked and repulsed, and Elton abandons her in a parking lot far from home. She is immediately mugged, and is forced to call Josh from a payphone to ask for a lift. On the drive home, Cher suggests that they pick up food for Mel and his colleagues, who are working on a difficult case at the house. Impressed by this considerate suggestion, Josh begins to form a new opinion of her. Another transfer student, the suave and handsome Christian (Justin Walker), arrives in Mr. Hall's debate class. Cher is taken with him immediately, and considers breaking her own rule of never dating a high school boy. The two become friends, and soon plan to attend a party along with Tai. Christian arrives at Cher's house to pick her up, and both Mel and Josh are put off by his relaxed, jazz-cat persona. Josh is clearly envious and tells Mel that he will trail them to the party for Cher's protection. While Cher and Christian bond on the dance floor, Tai self-consciously stands alone watching Elton dancing with his new girlfriend, Cher's snotty social rival Amber (Elisa Donovan). Josh arrives and dances with Tai to help her feel more included and comfortable. Cher is pleasantly surprised by this thoughtful gesture. Cher decides to move things forward with Christian, and invites him over one evening when her father is out. To her disappointment, he ignores her advances in favor of watching Tony Curtis movies. When driving with Dionne and her boyfriend Murray the next day, Cher laments Christian's lack of sexual interest in her, causing a highly amused Murray to point out that Christian is obviously gay. Embarrassed by her misconception of Christian, she abandons her romantic pursuit of him in favor of maintaining their genuine friendship. While at the mall with Cher and Christian, Tai experiences a traumatic incident when some male acquaintances nearly drop her over the upper-level railing as a prank. Christian angrily reprimands the culprits and comforts Tai, who is shaken but unharmed. Over the next few days, news of this dramatic event spreads throughout school, causing Tai's popularity to skyrocket. Cher watches, unnerved, as Tai is caught up in the attention, becoming the shallow, snobbish brat that Josh accused Cher of creating. Cher is further disturbed when Tai coldly rebuffs the sweet-natured Travis in favor of a more popular entourage. Cher, an atrocious driver with only a learner's permit, prepares to test for her license, but finds it difficult to focus after the shift in her friendship with Tai. She ultimately fails the driving test, and dejectedly returns home to find Tai and Josh playing a flirtatious game of hacky sack. Tai immediately speaks to Cher in private, excitedly revealing that she has overcome her disappointment about Elton because of her newfound attraction to Josh. Cher is startled by the discomfort she feels in response to this news, and tells Tai that she does not think Josh is a good match for her. Tai is affronted, and insults Cher before departing. Cher embarks on a solo shopping trip to clear her head, and realizes that she herself is in love with Josh. In an unusually vulnerable mood, Cher goes to her father for advice. Explaining that she is interested in a "do-gooder" type (though not revealing that her love interest is Josh), she expresses concern that she is too shallow and selfish to win his approval. Mel tenderly assures his daughter that she is an incredibly caring person, much like her late mother had been, who constantly goes out of her way to help her friends and family. Cher, heartened, resolves to become more compassionate on a wider scale. Not long after their fight, Tai approaches Cher apologetically and the two become friends again. After watching Travis participate impressively in a skateboarding competition, and after learning that he has given up his drug habit, Cher realizes that he is indeed worthy of Tai's affection, and is pleased when they reconcile. In an effort to impress Josh, Cher volunteers to help with a donation drive headed by Miss Geist for victims of the Pismo Beach disaster. Josh takes appreciative notice, and Cher herself feels unexpectedly fulfilled by engaging in this charitable endeavor. She and Josh also spend considerable time helping Mel and his colleagues process paperwork for their important case. While working with one of Mel's stressed-out underlings at the house, it is discovered that Cher had erroneously sorted some crucial documents, causing the panicked lawyer to cruelly insult Cher and storm out of the house. Cher is crushed, but Josh defends and comforts her, leading to them both revealing their feelings for each other. Mr. Hall and Miss Geist are married with many of their students in attendance, including Cher (who has brought Josh as her date), Dionne, Murray, Tai and Travis. The girls congregate as the bride prepares to throw the bouquet, and their boyfriends watch the ensuing scuffle with amusement until Cher triumphantly surfaces, bouquet in hand.
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