Content Warning: This section of the guide contains discussion of gender discrimination.

Gather initial thoughts and broad opinions about the book.

1. Which character did you identify with most, and why?

2. Did you find the ending satisfying or disappointing? Why?

3. Why do you think initial reviews of this book were so lackluster? How has this perception changed today?

4. How did your experience of this book compare with that of reading other works by this author, such as The Beautiful and the Damned or The Last Tycoon? Which is your favorite, and why? If this is the only novel by F. Scott Fitzgerald that you’ve read, what books would you compare it to?

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.