The Great Gatsby

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Several characters, most notably Jay Gatsby, create personas for themselves that contrast with their inner selves. Could you relate to this practice? Do you think most people engage in it to some extent?

2. The novel focuses on the disillusionment of the central character and, through him, the reader. Discuss a time in your life when you felt disillusioned with a person, place, or idea. Did that disappointment have a lasting impact on your worldview?

3. The Great Gatsby is widely assigned in US high school classrooms. In your opinion, what makes a book a good fit for this kind of educational setting? Are there books you remember reading in school that you look back on particularly fondly?

4. Consider the relationship between wealth and personal value as presented in the novel. Did this idea resonate with you, or did you find it to be misleading?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. Consider the novel’s depiction of “The American Dream.” Has this ideal ever been realistic? In what ways has America changed since Fitzgerald’s time, and do those changes make the novel’s critique more or less relevant?

2. The Great Gatsby was written long before the advent of the internet and social media. How would this novel have been different if it took place today? Would these technological developments have changed the outcome?

3. What role do gender politics and social expectations for women play in the novel? Does it offer any solutions to the problem of rigid gender roles?

Dive into the book’s structure, characters, themes, and symbolism.

1. Is Nick an unreliable narrator? Why or why not, and how can you tell?

2. Contrast the static and dynamic characters in the novel. Who changes the most? What might this characterization say about the novel’s perspective on gender?

3. Fitzgerald called this a novel of the “jazz age.” What does jazz represent in this story? Discuss what jazz might encompass beyond a musical genre.

3. Tom and Daisy arguably have the strongest relationship in the novel. Upon what is the strength of their relationship based? Is it love, or something else?