The title story of the collection, Goodbye, Columbus, was an irreverent look at the life of middle-class Jewish Americans, satirizing, according to one reviewer, their "complacency, parochialism, and materialism". It was controversial with reviewers, who were highly polarized in their judgments.
The story is told by the narrator, Neil Klugman, who is working in a low-paying position in the Newark Public Library. He lives with his Aunt Gladys and Uncle Max in a working-class neighborhood of Newark, New Jersey. One summer, Neil meets and falls for Brenda Patimkin, a student at Radcliffe College who is from a wealthy family living in the affluent suburb of Short Hills. The novella explores the classism which afflicts the relationship, despite the fact that Brenda's father, Ben, came from the same environment as Neil. The issue of assimilation is intrinsic, since Brenda is more assimilated than Neil. The title, Goodbye, Columbus refers to a record that Brenda's brother Ron listens to from his years as an athlete at The Ohio State University, further proof of the Patimkins' success at assimilation. As the story proceeds, Neil finds that their relationship is falling apart. Thus, the title may be seen as a metaphor for Neil saying goodbye to the affluent, assimilated world of the Patimkins.