The Great Gatsby: A Reader's Guide for The Wild Gentleman Book Club
Inaugural Meeting - August 5th, 2025
The Wild Gentleman Book Club
This week marks the beginning of something special—a community of thoughtful men exploring what it means to live with purpose, integrity, and authentic connection. For the first book, I chose The Great Gatsby because it raises uncomfortable questions about success, love, and being a good man.
Meeting Details
We are meeting on Tuesday, August 5, at Paddy's Public House in West Newton. The first group is small and experimental, and I am looking forward to starting something special with this group.
I have been sending out messages about the book club via this newsletter, The Wild Gentleman Instagram account, and through some chats. If you missed out on any of these and want to come to discuss The Great Gatsby or just to be part of this community in its earliest days, you can find all the information on the meeting here: The Wild Gentleman Book Club - Meeting #1.
Below is a reading guide to prepare for the first book club get-together. I'll be using this as a guide. Also, you can get a shorter, printable Reading Guide here.
Why The Great Gatsby for Men in 2025?
Experience: When I taught this to middle schoolers, they saw romance. Reading it as an adult man, other themes stand out: the true nature of relationships and friendships, and the difference between wealth and worth.
Reflecting Modern Struggles: Gatsby's story reflects many topics that The Wild Gentleman seeks to explore: public success versus private fulfillment, the idealization of performance over authenticity, and the challenge of building genuine relationships in a world that values status over character.
Moral Complexity: Every character in this novel is flawed. There are no heroes, only human beings making complicated choices. This creates space for honest discussion about our own contradictions and challenges.
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 yourself do you hide, or which do you perform differently?
- 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 Focused on Characters
- 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?
Deeper Questions To Dig Into
- 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?
Quotes Worth Discussing
On authenticity:
"I like large parties. They're so intimate. At small parties there isn't any privacy."
On moral complexity:
"They were careless people, Tom and Daisy—they smashed up things and creatures and then retreated back into their vast carelessness."
On friendship:
"I wanted to get somebody for him. I wanted to go into the room where he lay and reassure him: 'I'll get somebody for you, Gatsby. Don't worry. Just trust me and I'll get somebody for you—'"
Preparing for Future Discussions
Future Book Club Selections
Please share books you think we should feature for the monthly book club as we advance. I want the community to help pick the monthly books going forward after September.
Please email me here: dennis@thewildgentleman.com
September Preview
Our following selection (Man’s Search for Meaning by Viktor Frankl) will build on tonight's themes while exploring different aspects of what it means to be a thoughtful man in a complex world.
Final Thoughts
The Great Gatsby is considered a quintessential American novel. Why? It doesn't offer an All-American outline about how to live a good life. Instead, it shows us the complexity of human motivation, the cost of our choices, and the challenge of building authentic relationships in a world that often rewards performance over substance.
This week, we begin building something different. In this community, men can explore these questions together, support each other's growth, and discover that the most meaningful adventures often happen in conversation with other thoughtful people.
Unlike Gatsby’s pursuit of Daisy, I believe we are aiming to build something lasting and true with this book club: The possibility of creating an authentic community through literature, honest conversation, and mutual support.
Welcome to The Wild Gentleman Book Club. Let's see where this conversation takes us.
"And so with the sunshine and the great bursts of leaves growing on the trees, just as things grow in fast movies, I had that familiar conviction that life was beginning over again with the summer."
