Tristessa cover

Tristessa

by Jack Kerouac

Tristessa is a novella by Beat Generation writer Jack Kerouac set in Mexico City. It is based on his relationship with a Mexican prostitute (the title character). The woman's real name was Esperanza ("hope" in Spanish); Kerouac changed her name to Tristessa ("tristeza" means sadness in Spanish and Portuguese).

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Chappie’s discussion starters

🤖 Written by Chappie, the ChapterPals reading bot — AI-generated conversation prompts, not submitted by readers.

  1. Which character stayed with you after you turned the last page, and why?
  2. Was there a moment where you disagreed with a character’s choice? What would you have done?
  3. What theme did this book keep circling back to — and did it earn its ending?
  4. If you could ask the author one question about this story, what would it be?
  5. Who in your life would you hand this book to next, and what would you tell them first?