In Chicago, the art dealer Brooke Meyers feels not appreciated and neglected by her immature boyfriend Gary Grobowski, 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.

In Ohio, Priscilla Chase is the VP of a company that works bringing new business to Cleveland. She has been married for more than ten years with Jack Chase, the biology teacher from the local public school. Priscilla is successful in her career but is frigid and has never reached an orgasm, hurting her frustrated husband. When Priscilla decides to buy a vibrator, Jack is seduced by his teenage student Kristen Taylor and recovers his self-esteem, working out, losing weight and dressing adequately. Priscilla has new sexual experiences and becomes closer to Wayne the Pool Guy, the constructor of swimming pools in her neighborhood since she was a child. The new relationships upgrade the personal and professional lives of Priscilla and Jack.

For newlyweds Carl and Molly Peterson, life can't get any sweeter as they begin anew to settle down into married life. With a nice house and established careers in tow, nothing seems to get in their way. However, Carl is about find out just how much friendship means when Dupree, his best friend has been displaced from his home and fired from his job because of attending their wedding. Taking his friend in, what Carl and Molly are about to experience is that the fine line between a few days and whatever else is after, can be a lot more than they bargained for. Especially when their friend overstays his welcome in far too many ways than he should.

Two wealthy sisters, both heiresses to their family's cosmetics fortune, are given a wake-up call when a scandal and ensuing investigation strip them of their wealth.