Stacy Holt (Brittany Murphy) an associate producer for a daytime talk show is bemused by her boyfriend Derek's (Ron Livingston) unwillingness to talk about his previous relationships. Sneaking a look at his Palm Pilot diary she takes down the details of a host of former girlfriends and starts interviewing them under the (false) pretence that the results are to be for a show she's producing. She's desperate to find out why his relationships didn't work out in the past and how she