An associate producer (Brittany Murphy) for a daytime talk show, whose boyfriend is "commitment-phobic", sneaks into his Palm Pilot and starts interviewing all of his old girlfriends -- under the false pretenses that it has to do with the show -- to find out why his relationships didn't work in the past, and to find out if he's worth her trust over the long haul. Her plan goes awry when she becomes friends with one of them, and she must reveal who she really is.