Coming of age in 1959, a naïve college junior leaves a small town in Southern Illinois to spend his summer vacation in Chicago. He is staying with his mother’s childhood friend, Dearie, who is Jewish, separated from her husband, lonely, and an alcoholic. Another family friend, a vice president at Chicago and Northwestern Railroad, orders the chief draftsman there to give him a job. Bruce has adequate skills for the task, but his two, few years older, married colleagues are jealous of his youth and freedom. The chief draftsman resents the way he was hired. Bruce is eager to explore an adult world in the big city where he hopes to repair a broken relationship with the love of his life. She is the reason he has made this trip, but things go sideways at a birthday party given to her by the male employees at a sheet metal shop where she works as a secretary. A would-be suitor slips him a Mickey Finn that terminates both the party and his love life. Dearie and Bruce find themselves alone, together. They are perfect for each other at this time and place and begin a summer that will never be forgotten.