A Reader's Guide for The Great Gatsby
The Wild Gentleman Book Club
Key Themes for Discussion
1. The Performance of Success
Gatsby creates a false identity to win love and acceptance.
Questions for Reflection:
- How do successful men today perform rather than simply be?
- What aspects of our own lives are "performance" versus authentic expression?
- How does social media amplify the pressure to perform successfully or at least to imply some levels of success?
2. Love vs. Obsession
Does Gatsby love Daisy or his idea of her?
Questions for Reflection:
- What's the difference between loving someone and loving the idea of them?
- How do we distinguish between a healthy pursuit and a destructive obsession?
3. Friendship and Loyalty
Nick's relationship with Gatsby seems to be one of the few genuine connections in the novel.
Questions for Reflection:
- What does real friendship look like between adult men?
- How do we support friends who are making destructive choices?
- What do we owe our friends versus what we owe ourselves?
- Is Nick actually in a healthy relationship with Gatsby?
4. Class and Authenticity
The novel exposes a brutal reality of American class distinctions.
Questions for Reflection:
- How do class dynamics still play out in professional and social settings?
- What does it mean to "belong" versus simply having access?
- How do we navigate professional advancement without losing authenticity?
More Discussion Questions
- What's your first impression of Nick as a narrator? Is he reliable? Why does this matter?
- What draws Nick to Gatsby initially? What draws us to charismatic but mysterious people?
- When we learn Gatsby's real background, does it change your perception of him?
- Gatsby says you can "repeat the past." Do you agree? What past moments do men often want to recapture?
- Why doesn't Daisy live up to Gatsby's dream of her? What does this teach us about idealization?
- How is Tom's affair different from Gatsby's pursuit of Daisy? What does this reveal about character?
- Why does Nick stick with Gatsby even after learning the truth about him?
- What does Gatsby's death symbolize? Why is Nick the only one who cares?
Questions Beyond the Book
- Have you ever achieved something you wanted badly, only to find it didn't fulfill you the way you expected?
- How do you measure success now versus how you measured it at 25?
- How do professional success and social expectations affect your ability to form genuine friendships?
- What aspects of yourself do you hide or perform differently in professional versus personal settings?
- How do you maintain authentic relationships while navigating social and professional hierarchies?
- How do you distinguish between healthy ambition and destructive obsession?
- What would you do if you realized a long-held dream was actually an illusion?
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