In Chicago, the art dealer Brooke Meyers(Jennifer Aniston) feels not appreciated and neglected by her immature boyfriend Gary Grobowski(Vince Vaughn), who is partner of his two brothers in a tourism business, and decides to break-up with him to make Gary misses her. Gary misunderstands her true intention, both follows the wrong advices of family members and friends, beginning a war of sexes with no winner.
