1. The notion of the American dream figures prominently in this story. How should readers define "American dream"? Moreover, is pursuing the American dream necessarily a good thing, as evidenced by The Great Gatsby?
2. Explore the character of Nick. How are readers supposed to feel about him? In what ways does he come off as reliable or unreliable?
3. Fitzgerald's story shows the clear delineations between different strata of society: new money, old money, some money, and no money. How are readers to interpret his comments on each of these groups? Does he hold any one group above the other? Are there ways in which people of all groups are alike?
4. Throughout the story, Gatsby has difficulty accepting that the past is over and done with. Where do you find evidence of his trying to recapture the past? What does this say about him? Should people live their lives yearning for something in the past? Why or why not?
5. Part of Fitzgerald's strength as a writer comes from his imagistic style. His writing is very sensory-oriented. What examples of sensory-oriented imagery (sight, taste, touch, smell, sound) can you find in the story? What kind of atmosphere do these details help create? How do they affect you as a reader?
6. It is not uncommon to hear the term "a self-made man." In what possible ways might this term be explained? How does Gatsby fit that definition? In what ways does he take it too literally?
7. Although Gatsby professed to love Daisy, there is a sense that he was not in love with her as much as he was in love with the idea of her. Where can you find evidence of Gatsby's devotion to an ideal rather than an actual person?
8. Although Nick Carraway has his reservations about Gatsby, it is clear he thinks of him fondly; after all, he titles the book The Great Gatsby. He leads a questionable existence and comes to a tragic end, yet Nick (and by extension, the readers) feels empathetic toward him. Does Gatsby deserve to be called "Great"? In what ways is he great? In what ways is he not? In the end, which wins out: greatness or mediocrity?