Stacy (Brittany Murphy) works as an assosiate producer on a tv talk show called Kippie Kann played by Kathy Bates. She is staying with her boyfriend Derek (Ron Livingston) and stumbles upon his 'little black book'. The device shows Stacy that her boyfriend has pictures and phone numbers of several ex-girlfriends. She decides to meet each one of the ex's personally in an attempt to get closer to Dereks past life and ends up becoming friends with one of the ex's. However Stacy is set up by her colleague Barb (Holly Hunter) as she has kept track of everything Stacy has done with the Palm Pilot -the little black book- and stages her on a live performance of the talk show and Stacy ends up losing her boyfriend to the ex she became friends with. The end of the film shows Stacy getting a new, better job and meeting her idol Carly Simon.