The novella "Goodbye, Columbus" was first published in Roth's 1959 collection, Goodbye, Columbus, and Five Short Stories, which won the National Book Award. Other stories in the collection include "The Conversion of the Jews," "Epstein," "Defender of the Faith," "You Can't Tell a Man by the Song He Sings," and "Eli, the Fanatic." "Goodbye, Columbus" was adapted to the screen in the 1969 movie by the same title, produced by Paramount, directed by Larry Peerce and starring Ali McGraw and Richard Benjamin.

"Goodbye, Columbus" is narrated from the point of view of Neil Klugman, a twenty-threeyear- old Jewish man who lives with his aunt and uncle in a lower-middle-class neighborhood in Newark, New Jersey, and works at a public library. It concerns his relationship over the course of one summer with Brenda Patimkin, an upper-middleclass Jewish college student staying with her family in the suburbs. Their relationship is characterized by the stark contrast of their socioeconomic differences, despite the fact that they are both Jewish. The summer ends with Brenda's brother Ron's wedding, after which Brenda returns to Radcliffe College in Massachusetts. When the two arrange to meet at a hotel over the Jewish holidays, she tells him that her parents have discovered her diaphragm and have both written her letters expressing their dismay and their disdain for Neil as a result. As Brenda feels she can no longer continue the relationship, Neil leaves the hotel, ultimately achieving a new sense of self-knowledge, which is expressed by the dawning of the Jewish New Year as he arrives back in Newark.

"Goodbye, Columbus" explores themes of Jewish identity, class divisions within the Jewish community, spiritual crisis over Judaism, love, sex and relationships, and the struggle for self-knowledge in a young man. Despite its serious subject matter and themes, the novella is characterized by humor, as expressed through the narrator's finely tuned sense of irony in his observations of both his own and his girlfriend's families.