Discussion questions for calypso

  1. Middle age and mortality are recurring themes. How does Sedaris use humour to explore these heavier topics?

  2. The essays often center around Sedaris’s family. Which family dynamics felt most relatable or surprising to you?

  3. In “Now We Are Five,” Sedaris reflects on the loss of his sister Tiffany. How does this essay shape the emotional tone of the collection?

  4. Sedaris frequently discusses his partner Hugh. What role does Hugh play in grounding or challenging Sedaris’s worldview?

  5. How does the beach house, the “Sea Section,” function as a symbol throughout the book?

  6. Sedaris is known for his observational wit. Were there moments where his humour felt too sharp or perfectly timed?

  7. How does Sedaris balance vulnerability with sarcasm? Did you find one more effective than the other?

  8. What did you make of Sedaris’s reflections on aging and his changing relationship with his body?

  9. Were there any essays that stood out as particularly poignant or laugh-out-loud funny?

  10. How does Calypso compare to Sedaris’s earlier works, if you’ve read them?