Beverly Donofrio (Drew Barrymore) is a young girl with hopes and dreams for herself, but has terrible luck with boys. Her best brined in life is Fay Forrester (Brittany Murphy) who shares the same bad luck. Beverly gets pregnant by Ray Hasek (Steve Zahn), a drug-addicted loser and she is forced to marry him by her parents. Beverly’s father, Leonard Donofrio (James Woods), is a local cop and has very traditional family values. The movie follows Beverly’s life over the next couple decades. She continually feels tied down by Ray and her family. She even feels tied down because of her son. She tries and tries to escape her life, but only loses more each time she does. She needs to learn the value of what she does have before she loses everything.