Clueless is a loose adaptation of Jane Austen's 1815 novel Emma, and many of its characters have counterparts in the novel.[41][42][43]
- Cher Horowitz/Emma Woodhouse: Cher is representative of the main character Emma Woodhouse. Spunky, carefree, entitled, perpetually single, and matchmaker extraordinaire, both Cher and Emma enjoy the satisfaction of helping those who are without love find a perfect match. This is first seen within the first fifteen minutes of the film when both she and Dionne pair their English teacher with the school's Debate teacher. However, this is more prominently reflected when Cher does everything in her power to pair her newest friend Tai. While both Emma and Cher mean well in their matchmaking attempts, neither of them realizes the depths of her actions nor her feelings towards Josh/Mr. Knightley until Tai/Harriet asks her to set her up with Josh/Mr. Knightley.
- Josh/Mr. Knightley: Cher's former stepbrother, whom she finds utterly repulsive. At the beginning of the movie, she states that she has no positive feelings towards Josh in the slightest. The two bicker continually. However, as the movie progresses, Josh is shown to be more caring and considerate towards Cher, becoming defensive towards her choices of men and in life. In the novel, Mr. Knightley is the brother of Emma's sister's husband and is Emma's only critic. Cher/Emma and Josh/Mr. Knightley eventually realize they are in love.
- Tai/Harriet Smith: Tai, representative of the young, fair, and socially awkward Harriet Smith, is a newcomer to Bronson Alcott High School. Soon after, she is swept off her feet by both Cher and Dionne as they help her (unintentionally) become the most popular girl in school, to Cher's dismay. At the beginning of the film, Tai is attracted to Travis, a well-meaning, skateboard-riding, pot-smoking social recluse. Harriet is likewise attracted to humble farmer Robert Martin. Each is pressured by Cher/Emma to reject her lower-status potential lover, instead being pushed towards Elton/Mr Elton. Disastrously for Cher, Tai then falls for Josh. Emma is likewise horrified when Harriet falls in love with Mr. Knightley. In both cases, this leads to the heroine examining her own true feelings.
- Mel Horowitz/Mr. Henry Woodhouse: Similarly to Emma, Mr. Horowitz is a well known and respected man within his circle of friends, though there is one major difference between both characters: while Mr. Horowitz is shown to have little to no care for his health, Mr. Woodhouse is considered to be a valetudinarian. Both characters are shown to love their daughters greatly while not always being so forward in their affection.
- Christian/Frank Churchill: The initially appealing love interest of Cher, whom she convinces herself she must be in love with, similar to Frank Churchill in the book. In the book, Churchill is not available to Emma because he is secretly already engaged; in the film, Christian is not available to Cher because he is gay. Both characters engage in surface-level flirting with the heroine and make her consider her own feelings.
- Travis/Robert Martin: A stoner and skater who has a mutual attraction with Tai; however, their attempts at courtship are derailed for a time by Cher's attempt to set Tai up with Elton. Travis is an underachiever, is constantly late for class and often receives poor grades. In the book, Emma considers Martin, a farmer, to be beneath Harriet.
- Elton Tascia/Mr. Elton: Elton is a popular student whom Cher attempts to fix up with Tai. As is the case with the Elton from the book, he is not interested in Tai/Harriet and mistakenly believes that Cher/Emma is interested in him.
- Amber/Mrs. Elton: Cher's antagonist, who is implied to be dating Elton after Cher turns down his advance, similar to Mr. Elton taking a wife after Emma rejects him.
- Miss Geist/Miss Taylor and Mr. Hall/Mr. Weston: The initial targets of Cher's/Emma's matchmaking.
