- Directors: Peyton Reed
- Producers: Vince Vaughn, Scott Stuber
- Writers: Vince Vaughn, Jeremy Garelick, Jay Lavender
- Genres: Comedy, Drama, Romance
- Actors: Vince Vaughn, Jennifer Aniston
A bickering couple, immature, iresponsible Gary (Vaughn) and Brooke (Aniston), live in a condo in Chicago. Both are driven in their careers, with Gary working as a city tour business guide in his brothers’ company and Brooke working in an art gallery. Early in the movie, they separate after a bitter argument. Their conflicts are largely due to Gary’s immaturity and inflexibility.
Their social backgrounds contribute to the division that becomes apparent between them. Brooke has applied feng shui books from her mother in the interior design of her and Gary’s condo; her brother Richard is part of an a cappella group called The Tone Rangers; her friend Addie uses phrases of advice such as “Remember, we’re always owning our actions, right? And we’re always healthy with it, yes?”; and Brooke bemoans how many times she has dropped “hints about the ballet” to Gary, but to no avail. By contrast, Gary likes action-oriented teen video games, is an avid Chicago sports fan, and wants a pool table in the condo. Brooke is fighting for their relationship to stay alive. However, the condo ends up becoming the subject of a war in which both try to outwit and outdo each other through blind dates, drunken parties, and broken promises.
Gary, realizing what he has lost, returns to his tour business while Brooke travels the world, eventually finding her way back to Chicago. At the end of the movie, they meet again by chance on the streets of Chicago. After some awkward but friendly catching up, they part ways but catch each other glancing over their shoulders and share a smile.