The Great Gatsby reflects an era that may be like our own, in many ways. A great deal of thought might be given to the ways in which Fitzgerald represents an age with problems and impulses that may be found in today's troubled world. Some thought may be given to how historically accurate Fitzgerald's picture of the 1920s is, how much of what he presents is "real," in the same manner that historians and journalists often attempt to detect the realities of the 1960s and the current period. Topics that might be discussed are the idealism and the prejudices of the time — such discussions of a postwar period have been especially stimulating over the years, and Fitzgerald was, more than most, affected by the unsettled times after World War I.
Another useful approach is to compare the film(s) and novel. It is also interesting to discuss whether Nick or Gatsby should have narrated the story.
1. What are the chief symbols in the novel, and what do they represent (e.g., the light on Daisy's dock and the eyes of Dr. Eckleburg)?
2. Does the vagueness of Gatsby's background and somewhat criminal activity cause the work to be less effective than a more detailed presentation would achieve? What details might be included in order to create a fuller picture of the protagonist?
3. Is Nick Carraway's admiration of Gatsby truly supported by the text of the novel? Should there be more of an objective reason for this feeling? Or, is it adequately supported by the text?
4. In what ways does Gatsby seem to be a product of his time and place?
5. Can the reader derive from the book a real sense of the postwar feeling of loss of values and even "quiet desperation?"
6. Do you sympathize with Gatsby? What qualities of his create your reaction? Is he at all really "great?"
7. Is the conclusion of the novel too contrived? Could it have been made more realistic, more credible? How?
8. Does the relationship between Nick Carraway and Jordan Baker in any way parallel that between Gatsby and Daisy Buchanan? Was there an intention by Fitzgerald to create an effect thereby?
9. How big a part does "illusion" play in the book, and does a real sense of "disillusion" permeate the text?
10. What seems to be the prevailing "tone" of the work. Does it enhance the impact of the text on the reader?