Near the end of their senior year of high school, noble underachiever Lloyd Dobler (John Cusack) falls for valedictorian Diane Court (Ione Skye) and plans to ask her out, though they belong to different social groups. Lloyd's parents are in England on Air Force duty, so he lives with his sister Constance (Joan Cusack, uncredited), a single mother, and has no plans for his future. Diane comes from a sheltered academic upbringing and lives with her doting divorced father Jim (John Mahoney), who owns the retirement home where she works. She is due to take up a prestigious fellowship in Britain at the end of the summer.