Clueless (1995)
This is one of the best high school rom-coms ever. This film is an adaptation of Jane Austen's "Emma" but fit into the late-90s realm. Alicia Silverstone is the best face for Cher, who is obsessed with throwing fancy parties and picking out her outfit to match her purse for that day. You know, high school things. Her romance is with her ex-stepbrother (Paul Rudd) which feels weird but kind of works.
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