Hoping to distract themselves from the tragic death of their infant daughter, Leona and Bill Hart (Kathleen Quinlan and Michael Ontkean) take a vacation to Jamaica, leaving their pre-adolescent son, David, alone in their lakefront estate outside Baltimore, Maryland. While wallowing in grief, Leona accepts the frank advice of the hotel maid, Clara Mayfield (Whoopi Goldberg), and impulsively invites her to work as their housekeeper. Although David initially responds to her with hostility, he and Clara develop a close bond after learning that his parents have decided to separate. A short time later, Bill begins dating an interior designer, while Leona develops a relationship with Dr. Peter Epstein, author of a popular self-help book. David despises that they have placed their happiness above his own, and begins spending more time with Clara in her new Baltimore apartment. One weekend, the boy learns that Clara is hiding a dark secret about her son, Ralphie, and discovers a stack of letters stashed under her bed.