A smooth-talking ad executive attributes his remarkable success with women to his ability to manipulate their emotions from the moment he first meets them. When his teenage nephew drops in for a visit, he soon learns that his approach isn't as foolproof as he thought when he attempts to teach the boy how to pick up women.

A fascinating and touching portrait of isolation in big cities, Roger the Dodger features an extended interview with a man who was arrested by the police for loitering near a train station. The man shares his discontent with the local government, and American politics at large. An avowed Marxist, he thinks that carrying a picture of Fidel Castro when arrested probably did not endear him to the police. He discusses his thoughts on loneliness, specifically the ways in which big cities such as Chicago and New York contribute to feelings of isolation, particularly for those who do not enjoy popular pastimes such as sports and rock music.