Rob (John Cusack John Cusack) is a music enthusiast who runs a record store where two clerks, Dick and Burley, are music lovers. One day, Rob's girlfriend Lola (Eben Yeyou Iben Hjejle) broke up with him, and he didn't even know why. To this end, he made his own list of lovelorn, reviewing the failed relationships along the way. He found himself always acting as the dumped party, so he decided to recontact the ex-girlfriends and ask them why they chose to break up in the first place. At the same time, Laura kept in touch with Rob because she was moving out of his place. Once, Rob learned from a friend of Lola that Lola had started dating Ian (Tim Robbins), who lives upstairs. This hit Rob so hard that he began to keep calling and harassing Lola and Ian, wandering downstairs. Finally, one day, when the connecting flight arrived, Laura told Rob that her father had passed away.
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