The self-destructive and needy wealthy teenager Harold is obsessed by death and spends his leisure time attending funerals, watching the demolishing of buildings, visiting junkyards, simulating suicides trying to get attention from his indifferent, snobbish and egocentric mother, and having sessions with his psychologist. When Harold meets the anarchist seventy-nine-year-old Maude at a funeral, they become friends and the old lady discloses other perspectives of the cycle of life for him. Meanwhile, his mother enlists him in a dating service and tries to force Harold to join the army. On the day of Maude's eightieth birthday, Harold proposes to her but he finds the truth about life at the end of hers.

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