Sideways cover

Sideways

by Rex Pickett

Sidewaysis the story of two friends--Miles and Jack--going away together for the last time to steep themselves in everything that makes it good to be young and single: pinot, putting, and prowling bars. In the week before Jack plans to marry, the pair heads out from Los Angeles to the Santa Ynez wine country. For Jack, the tasting tour is Seven Days to D-Day, his final stretch of freedom. For Miles--who has divorced his wife, is facing an uncertain career and has lost his passion for living--the trip is a weeklong opportunity to evaluate his past, his future and himself. A raucous and surprising novel filled with wonderful details about wine, Sidewaysis also a thought-provoking and funny book about men, women, and human relationships.

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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?