1. The novel's action occurs in 1922 between June and September. How does Nick's nonchronological narration shape your response to the events surrounding the mystery of Jay Gatsby?
2. Nick believes he is an honest, nonjudgemental narrator. Do you agree?
3. Gatsby believes that the past can be repeated. Is he right?
4. Why does Daisy sob into the "thick folds" of Gatsby's beautiful shirts?
5. What do the faded eyes of Doctor T.J. Eckleburg symbolize? Is there a connection between this billboard and the green light at the end of Daisy's dock?
6. Perhaps the novel's climax occurs when Gatsby confronts Tom in New York. Did Daisy's ultimate choice surprise you? Is it consistent with her character?
7. Do you agree with Nick's final assertion that Gatsby is "worth the whole damn bunch put together"? Why or why not?
8. How does Fitzgerald foreshadow the tragedies at the end?
9. Does the novel critique or uphold the values of the Jazz Age and the fears of the Lost Generation?
10. Fitzgerald wrote, "You don't write because you want to say something, you write because you have something to say." What did he have to say in Gatsby?
11. Fitzgerald scholar Matthew J. Bruccoli claims: "The Great Gatsby does not proclaim the nobility of the human spirit; it is not politically correct; it does not reveal how to solve the problems of life; it delivers no fashionable or comforting messages. It is just a masterpiece." Do you agree?

If you're intrigued by the 1920s, you might enjoy reading:
Ernest Hemingway's The Sun Also Rises (1926)

If you're intrigued by novels about lives of privilege, you might enjoy reading:
John O'Hara's Appointment in Samarra (1934)

If you're intrigued by the Fitzgeralds, you might enjoy Zelda's only novel:
Zelda Fitzgerald's Save Me the Waltz (1932