A Reader's Guide for The Old Man and the Sea

The Wild Gentleman Book Club

Key Themes for Discussion

On Aging and Masculinity

"You are killing me, fish, the old man thought. But you have a right to. Never have I seen a greater, or more beautiful, or a calmer or more noble thing than you, brother."

How does Santiago's model of aging masculinity differ from the cultural messages we receive about staying young, staying relevant, staying productive?
What does it mean to age with dignity in a world that often treats older men as either irrelevant or as objects of pity?

On Solitude and Connection

Santiago's solitude seems both chosen and imposed. How do modern men navigate the tension between independence and isolation?
How does the masculine ideal of self-sufficiency sometimes prevent us from the connections we actually need?

On Mentorship

Who are the younger men in your life who might benefit from your experience, even (or especially) when you feel past your prime?
How do we mentor in an age where formal mentorship feels awkward or rare between men?

On Resilience and Purpose

When have you experienced the sharks taking your marlin—working hard for something only to have it stripped away? How did you respond?⠀

Discussion Questions

1. How does reading this book as an adult differ from reading it (or being assigned it) in high school? What stands out now that didn't before?

2. The relationship between Santiago and the boy is tender in a way that's rare in literature about men. What does the boy's defiance of his parents to care for Santiago tell us?

3. Santiago repeatedly calls the fish his brother, respects him, loves him—and still kills him. How do you understand this? What are the "worthy opponents" in your life that you respect even as you struggle against them?

4. Are the sharks villains, nature taking its course, or a metaphor for something deeper in life that Hemingway wants us to come to a conclusion about on our own?

5. Santiago returns with nothing but the skeleton in the final pages of the story. Does this make this tale a tragedy? A triumph? Both?

6. Santiago reflects: "I may not be as strong as I think... But I know many tricks and I have resolution." How does this conception touch on ideas of what strength and manliness mean in relation to age? What are the "tricks" older men have that younger men don't?

7. At the end, despite everything, Santiago still has, and has maybe even added to, his legacy as a fisherman. The boy seems to hold him in higher regard. He has not lost what matters most. Is there anything in your life that has been like this, achieving something, losing it, yet keeping that which is most valuable?⠀