Robert Longfellow is a playwright whose latest play in New York City has just bombed while his marriage is in no better shape. Seeking an escape, he travels back to Los Angeles to visit his mother, meet a dear secret girlfriend and decide on new writing opportunities. However, everything changes when his brutish childhood neighbor, Gus, takes Robert hostage with the police surrounding the house. In this situation, the strained conversations inside drift to Robert's profession and the nature of creative writing. To placate Gus, Robert introduces him to improvisational dialogue and the pair engage in some dramatic exercises. However as they perform, the material becomes more personal as the trapped pair confront each other with hard truths that will leave neither of them unscathed.

Former major-leaguer Tony Micelli and his daughter Samantha arrive at the Connecticut household of executive Angela Bower, where Tony has taken a job as live-in housekeeper. The Bowers are an interesting family, to say the least. Angela is uptight and obsessed with her work. Her son Jonathan is shy and lacks self-esteem, and her mother, Mona, is a man-hungry vixen. Tony soon wins them over with his laid-back style, and the Bowers soon begin to loosen up. Over time, romantic tensions begin to surface between Angela and Tony, and we see the children grow up.