1. Discuss how places and settings used throughout The Great Gatsby epitomize various aspects of American society during the 1920s. Contrast the setting of the Valley of Ashes with that of East Egg and West Egg.
2. On the surface, The Great Gatsby is a story of the thwarted love between a man and a woman. The main theme of the novel, however, encompasses a much larger, less romantic scope. It is a highly symbolic meditation on 1920s America as a whole, in particular the disintegration of the American Dream in an era of unprecedented prosperity and material excess. Discuss the various symbols used throughout the novel. Some examples include: the green light, the Valley of Ashes, and the eyes of Dr. T.J. Eckleburg.
3. What is Nick like as a narrator? Is he a reliable storyteller, or does his version of events seem suspect? How do his qualities as a character affect his narration?
4. Compare and contrast Gatsby and Tom. How are they alike? How are they different? Given the extremely negative light in which Tom is portrayed throughout the novel, why might Daisy choose to remain with him instead of leaving him for Gatsby?
5. Discuss Gatsby’s character as Nick perceives him throughout the novel. What makes Gatsby “great?”
6. What does The Great Gatsby say about the relationship between the American Dream and the accumulation of wealth?
7. What makes The Great Gatsby an American classic? Do you think the book is still relevant?
8. Discuss Fitzgerald’s use of the automobile in this novel. What do you think might have made the automobile an appealing symbol to Fitzgerald in the early 1920s?
9. Compare and contrast the characters of Daisy and Myrtle Wilson.
10. Tom and Daisy, we are told, drifted around before settling in East Egg, and Nick expects them to continue to drift. Other characters in the novel, while not drifters, appear to be rootless. How much does rootlessness have to do with the characters’ problems?
11. Nick says that Gatsby “represented everything for which I have an unaffected scorn,” and yet he also says that Gatsby “turned out all right in the end.” How do you explain Nick’s change of opinion?
12. One critic has written the “the theme of Gatsby is the withering of the American Dream..” What evidence in the novel supports this contention?
13. How does Fitzgerald use Gatsby’s parties to present a satirical portrait of the Roaring Twenties?
14. Discuss the relationship between Tom and Daisy. What do they have in common? Why do they stay together? Does their relationship change at all during the course of the novel?
15. Gatsby’s tragedy is that he chooses the wrong dream (Daisy). Has he been corrupted by society? Is his choice an indication that he is part of the corruption?

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