
In a game of baseball Gary (Vince Vaughn) is willing to link to the young and beautiful Brooke (Jennifer Aniston), an amateur who enjoys the game too. He succeeded and began a relationship in which they share a fabulous apartment in the city of Chicago.
But after 2 years of marriage, relationship is very difficult and after a small discuss that becomes a struggle beyond measure, and emotional demands of a couple in crisis, Brooke decides to break up her relationship with her boyfriend, Gary. She does not feel valued for the work done at home, and although she breaks the relationship, she tries to show him that he must change and value her in order to recover the relationship. But Gary is hurt, and through his friends and his brother, he tries to feel better with some new experiences, to forget that his wife has left him.
When he is not willing to leave the apartment they shared, the only solution is to continue living together as hostile roommates until one of the two sinks. They follow the wrong advices of family members and friends.
Gary is installed in the living-room of the apartment, where he makes strep-poker parties, plays the playstation, drinks beer and watches game summaries about baseball.
Brooke stays in the bedroom of the couple. She tries to make Gary jealous inviting handsome boys at home to go out for a drink or using weapons of naked women showing off at home.
When she is not getting the relationship back, she is disappointed in her room crying. Gary hears her and he decides to speak with her, then he realizes that she is right. Gary prepares a romantic dinner at the apartment, but Brooke comes with another boy, so Gary is shocked. The boy waits outside while they start to talk, but Brooke does not agree to have dinner with Gary.
One week later, the apartment is sold, they split the money and each of them decide to continue living separately. Gary will continue working as tourist guide, and Brooke will travel around the world, leaving for a season the gallery where she works.
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