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.

Frank is an expert professional safecracker, specialized in high-profile diamond heists. He plans to use his ill-gotten income to retire from crime and build a nice life for himself complete with a home, wife and kids. To accelerate the process, he signs on with a top gangster for a big score.