Nick and Russel, two air traffic controllers, compete for dominance in their work and outside of it. Nick gets ahead by fucking Russel’s wife (Angelina Jolie). But then, Russel may have gotten his revenge by fucking Nick’s wife (Cate Blanchett) too.
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip’s urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip’s mother. The division between the friends is further deepened when a cheating scandal engulfs the school.