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.
The film grossed over $205 million worldwide, with a total of $118.7 million at the American box office.
Critical response
On Rotten Tomatoes the film has an approval rating of 34% based on 192 reviews with an average rating of 5/10. The site's critical consensus reads, "This anti-romantic comedy lacks both laughs and insight, resulting in an odd and unsatisfying experience."[2] On Metacritic, the film has a score of 45 out of 100 based on 37 critics, indicating "mixed or average reviews".[3] Audiences polled by CinemaScore gave the film an average grade of "C+" on an A+ to F scale.[4]
Film critic Rick Groen of The Globe and Mail wrote, "Although possessed of a laudable desire not to be yet another run-of-the-mill, wacky-impediment—damned if the picture can figure out how to be an anti-romance comedy."[5]
The film was released on DVD on October 17, 2006. It has grossed $51 million in the US from DVD/home video rentals. It was later released on Blu-ray on June 3, 2014, and again on October 16, 2018.
A double-feature Blu-ray was released by Mill Creek Entertainment on October 5, 2021. The release contains the film and The Dilemma, which Vince Vaughn also starred in.[6]
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