Based on the autobiography of G. Gordon Liddy who spent 54 months in prison following the Watergate scandal.

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.

Harry is a shy hardware store employee. But whenever he takes a part in a local amateur theater production, he becomes the part completely--while on stage. Helene is new in town, a lonely itinerant telephone company employee. On a whim, she auditions for and gets the part of Stella to Harry's Stanley when the theater group performs A Streetcar Named Desire. Before anyone realizes the growing affection between Helene and Stanley, she falls deeply in love with the sexy brute, not knowing what the real man is like.