Jennifer (LEELEE SOBIESKI) is a 17-year-old girl who's just graduated from high school and is obsessed with death and the dark side of life. Still living at home with her excessively attentive mother, Sylvie (CAROL KANE), and stepfather, Bob (MICHAEL McKEAN), Jennifer spends most of her time being as different from the norm as possible, what with her Goth/punk look, multiple piercings, repeated visits to the cemetery and frequent writing of her own eulogy.
Not even remotely close to her long-estranged, hippie father, Ben (JOHN GOODMAN), Jennifer is lonely yet cynical, and finds her looks drawing stares from everyone, including Randall (ALBERT BROOKS), a 49-year-old, conservative manager of an upscale mall clothing store.
Jennifer has arrived there looking for a job so that she can move out of her mom's home, and despite Randall's initial reluctance, he decides to give her a break and hires her to work in the stockroom. The two eventually form an unlikely friendship, with each learning things about each other and their respective generations, as well as themselves.
Yet, when Randall suddenly falls ill, Jennifer finds herself on another mission. As nurse Patty (MARY KAY PLACE) cares for Randall, Jennifer searches for his long lost son, Randy (DESMOND HARRINGTON), hoping to find and then persuade him to meet his father.