Stacy (played by Brittany Murphy), an associate producer on a daytime talk show, is convinced that her boyfriend Derek (Ron LivingstonLittle Black Book is the right man for her, though he has an apparent phobia of commitment, and he refuses to talk about his past relationships. Taking the advice of colleague Barb (Holly Hunter), she looks at his Palm Pilot and its record of the names and numbers of three ex-girlfriends.

She sets up an interview with each woman, in an attempt to learn more about and get closer to Derek. However, Stacy's plan suffers a setback when she develops a friendship with one of the women.

Stacy eventually learns that Barb has orchestrated her meetings with the ex-girlfriends in order to bring them together on stage for a live broadcast during sweeps season. Unlike most romantic comedies, the film ends without the heroine succeeding in her love life.