Based upon the 1990 memoir of Beverly Donofrio titled Riding in Cars With Boys: Confessions of a Bad Girl Who Makes Good, the film begins in 1968 and takes us along the 20 years of her life between the ages of 15 and 35. It is the story of a woman (Drew Barrymore) who has a son while still a teenager, gets married to a drug addict (Steve Zahn), and then gets divorced. Eventually, she pulls herself out of welfare and goes to college to fulfill her dreams of becoming a writer.