Wild by Cheryl Strayed Discussion Questions

Instructor: Kerry Gray

Kerry has been a teacher and an administrator for more than twenty years. She has a Master of Education degree.

'Wild' is the true story of the author, Cheryl Strayed's emotional journey while hiking alone for three months on the Pacific Crest Trail. This asset offers discussion topics for high school classrooms reading this book.


When you are going through a dark period in your life, how do you cope? In Wild by Cheryl Strayed, the author's life seems out-of-control after surviving family dysfunction, her mother's death, and divorce. Realizing she needs to make some major changes, Cheryl decides to take a solo hike on the Pacific Crest Trail. As Cheryl learns about herself, students will reflect on their own experiences and coping skills. The following questions will support comprehension of this autobiographical novel.

Prologue & Part One

  • Why do you think the author chooses to include a Prologue? What do you learn about Cheryl during this section? How is Cheryl's lost boot a metaphor for life? What metaphor would you use to describe your life?
  • Describe Cheryl's relationship with her mother. What three adjectives would you use to describe Cheryl's mother? What are some ways she is similar and different from your mother? How does her mother's death impact Cheryl?
  • What role does Cheryl envision for herself after her mother's death? Why is this unrealistic? Compare Cheryl's dreams to Paul's dreams for their future. Do you think they could have realized their dreams together? Explain your answer. What implications does this have for choosing a marriage partner?
  • What are some ways Cheryl prepared for her journey? What are some ways she was unprepared? What can you learn about preparation from Cheryl's experience?

Parts Two & Three

  • Why did Cheryl decide to hike the PCT (Pacific Crest Trail)? What are some indications that Cheryl is not honest with herself? What do you think would have happened if Cheryl had not made this change?
  • What are some dangers Cheryl faces in the first part of her journey? Do you agree with her decision to hike alone? Explain your answer. Who are some of the people that help Cheryl along the way? Why is it important to accept help when it is offered?
  • How does Cheryl's stay at Kennedy Meadows prepare her for the rest of the hike? Why do you think it took Cheryl so long to agree to lighten her pack? What are some things you hold on to that just weigh you down?
  • Describe Cheryl's experience with therapy. Why do you think it was ineffective? How is hiking like therapy for Cheryl? What do you think she needs? What are some early signs that Cheryl is changing?

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