The movie centers on a middling playwright (Sheen) dealing with a midlife crisis and failing marriage to a wife (Monaghan) that is tired of being second fiddle to his work. The only person who understands his plight is his best friend, Alexander Taft (Goldblum), a behavioral psychologist with a midlife crisis of his own. Incapable of functioning in reality, Harold submerges himself in an elaborate play about his life.