Gary Grobowski and Brooke Meyers meet at
Wrigley Field during a
Chicago Cubs game and begin dating, eventually buying a
condominium together. Gary works as a
tour guide in a family business with his brothers, Lupus and Dennis. Brooke manages an
art gallery owned by eccentric artist Marilyn Dean. Their relationship comes to a head after the latest in an escalating series of arguments. Brooke, feeling unappreciated, criticizes Gary's perceived immaturity and unwillingness to work on improving their relationship. Gary is frustrated by Brooke's perceived controlling, perfectionistic attitude, and expresses his desire to have a little more independence, particularly when arriving home from work, wanting to unwind. Brooke becomes irritated when Gary fails to offer to help her clean up after a big dinner party at their home. Still frustrated from their unresolved earlier argument and feeling unappreciated, she breaks up with him (despite still being in love with him). Brooke seeks relationship advice from her friend Addie, while Gary talks things over with his friend Johnny. Since neither is willing to move out of their condo, they compromise by living as roommates; but each begins acting out to provoke the other in increasingly elaborate ways. Gary buys a pool table, litters the condo with food and trash, and even has a
strip poker party with Lupus and a few women. Meanwhile, Brooke has Gary kicked off their "couples-only" bowling team and starts dating other men, attempting to make Gary jealous. When their friend and
realtor Mark sells the condo, Gary and Brooke are given two weeks' notice to move out. Brooke invites Gary to an
Old 97's concert, hoping he will figure out that the gesture is meant to be her last-ditch attempt to salvage their relationship. Gary agrees to meet her but fails to understand Brooke's intentions and misses the concert—unwittingly breaking Brooke's heart. They fight one final time. Brooke says that Gary never matched her level of effort, and Gary retorts that Brooke was never clear about what she wanted. Later, Johnny points out that Gary has been selfish and emotionally distant from Brooke, dooming their relationship. Brooke quits her job to travel in
Europe. One evening, she brings a customer from the art gallery home. She finds the condo cleaned and Gary preparing a fancy dinner to win her back. He lays his heart on the line and promises to appreciate her more. For Brooke, it is too little too late, and she rejects the gesture. Gary seems to understand and kisses her before leaving. Both move out of the condo. Gary takes a more active role in his business, while Brooke travels the world, eventually returning to Chicago. Sometime later, they meet again by chance on the street. After some awkward but friendly catching up, they part ways but look back to smile at each other. ==Cast==