After Rob Gordon's girl friend Laura announces her decision to move out of his Chicago apartment, he muses about the danger of years of listening to maudlin pop songs about heartbreak and rejection. After Laura leaves, rejecting Rob’s pleas for her to stay, he recounts his all-time top five most memorable break-ups: Alison Ashmore, Penny Hardwick, Jackie Alden, Charlie Nicholson and Sarah Kendrew. At fourteen, Rob dated Alison for three days, after which she left him in favor of Kevin Bannister. Reflecting that every subsequent relationship has mirrored that one, Rob recalls Penny, the sweet sixteen-year-old who would not allow him to touch her breasts, but who, after he broke up with her, slept with the next boy she dated. In the present, Rob walks to Championship Vinyl, the record store he owns in an unfashionable part of the city. Like Rob, his employees, the awkward, nervous Dick and crude Barry, are fanatic music aficionados. Although Dick and Barry denounce any customer they deem inferior in musical tastes, Rob cannot fire them because they often work for free. He retreats to his office, where he remembers Charlie: In college, Rob meets the beautiful, dramatic Charlie and falls deeply in love. They date for two years, during which he adopts her punk style but feels insecure about his attractiveness, hipness and lovemaking abilities. His constant jealousy is substantiated when she leaves him for the sophisticated Marco. Coming out of his reverie, Rob muses that he has never recovered from this breakup. He then soundly berates Barry for chastising a customer, after which he reveals that Laura has left him. At home, Rob considers his relationship with Sarah, which was originally based on a mutual fear of being rejected, but ended when she left him for another man. Dick invites Rob to a local bar, but after Rob explains that he is organizing his record collection by autobiographical events, Dick, impressed, tries to help. Rob kicks him out, then fields a phone call from his mother, who breaks down in tears over the news that Laura has left. Frustrated, Rob joins Dick and Barry at the bar, where they rhapsodize over soulful singer/songwriter Marie De Salle, whom they later invite to the store. The next day, Rob stays home, knowing Laura is coming to pick up some boxes, and demands that she explain why she left him. She states that, although she has grown and changed over the past few years, he has remained steadfastly the same. Rob goes to the store, and after Laura’s friend Liz calls and mentions that Laura is seeing a man named Ian, even Marie’s surprise visit cannot distract Rob from neurotically wondering who Ian is. At home, he remembers that an Ian Raymond used to live upstairs from them, and that night, he stays awake torturing himself with images of Ian and Laura making love. At work the next day, Liz storms in and curses at Rob, prompting him to reminisce about the ease of the beginning of his relationship with Laura, whom he met while disc jockeying at a club. Rob now guesses that Laura has told Liz that Rob cheated on her while she was pregnant, thus provoking her to get an abortion, then borrowed $4,000 he could not pay back, after which he declared he was unhappy and “looking around for someone else.” As he rides the subway, however, Rob defends each of these actions, explaining that he did not know about the pregnancy or abortion, she offered the loan, and that she proclaimed her dissatisfaction with the relationship first. At home, hoping to find answers to why he is always rejected, Rob calls Alison’s mother. After learning that Alison married Kevin, Rob enthuses that he was rejected only because of a love that was destined to last. Inspired, he makes a date with Penny, who discloses that she was devastated when he broke up with her, and slept with the next boy out of confusion, resulting in a fear of sex that lasted for years. She runs off in tears, leaving Rob cheered by the thought that he abandoned her and not vice-versa. He then visits Sarah, whose intense depression stirs him to congratulate himself for not adding to her misery. Soon after, Laura visits Rob, and, although insisting there is little chance of reconciliation, delights him by revealing she has not yet slept with Ian. In celebration, that night he sleeps with Marie, whom he attracts by pretending to be sensitive, and about whom he forgets the next morning as soon as he leaves her apartment. He begs Laura to meet him, but after she admits that she has now slept with Ian, he spends the evening repeatedly calling her from a pay phone. The next day, Rob is pleased to receive an invitation to a dinner party from Charlie, but then is visited by Ian, an unctuous hippie who proposes “conflict-resolution.” Although Rob fantasizes about violently attacking Ian, he does nothing. At Charlie’s party, Rob realizes that she is pretentious and condescending, and feels only slightly hurt when she tells him that she preferred the “sunnier” Marco. Days later, as Barry plans to rehearse with his new band and Dick meets his new girl friend, Anaugh Moss, Rob goes home alone. There, he finds Laura, and after she leaves he lists the top five things about her that he misses, including her sense of humor and cute mannerisms. Later, Rob hears a piece of music he admires, and upon learning it was written by shoplifting skateboarders Vince and Justin, impulsively offers to produce their record on his label, which he names Top Five Records. He calls Laura, but she tearfully informs him that her father has died. Rob attends the funeral, but after Laura’s sister Jo and Liz insult him, he finds Laura and tells her that he is sorry, then leaves in the rain. He is sitting at the bus stop when Laura drives up and asks him to make love to her. Afterward, she tells him she is too tired not to be with him, and they go home together. For weeks, they enjoy a romantic reunion, but Rob soon meets pretty rock journalist Caroline Fortis and finds himself creating a compilation tape for her, a sure sign of his romantic interest. One day, he sees a poster Laura has put up advertising that he will D. J. at the release party for Vince and Justin’s band, and that Barry’s band, inauspiciously named Sonic Death Monkey, will play. Appreciating her faith in him, and finally realizing that he cannot just jump from relationship to relationship, Rob proposes to Laura, who laughs at him but is pleased that he is maturing. At the release party, Rob is a hit, and Barry shocks everyone by singing Marvin Gaye songs with great skill. While Vince and Justin steal CDs, Rob considers the compilation tape he will make for Laura, filled with all the songs that she likes, for once reflecting her tastes rather than his own.