1. Discuss the way Tiffany chooses to tell her story: the reader is immediately thrust into prison, and introduced to her as an inmate before they are introduced to her as a person. What do you think about the chronology of the book?
2. Tiffany weaves humor into the memoir’s narrative. Which of her actions and thoughts were most surprising to you? How does her sense of humor impact your reaction to the scenes? Do you feel the humor or sarcasm take away from her experience, or do you think they make it more accessible?
3. Tiffany structures her story so that many of the chapters end in a shocking reveal. Did you find this to be an effective strategy for drawing readers in? What was the most shocking or surprising moment of her story for you?
4. In Chapter 18, Tiffany reveals her experience in solitary confinement. Based on what you have read or seen on television regarding solitary confinement, do you find her experience shocking? Are you surprised by the kindness the guard extends to her?
5. Many people consider addiction to be a family disease. Discuss how Tiffany’s drug addiction – and recovery – impacts her closest relationships. How are different family members and loved ones affected?
6. Further to the above, discuss the differences between Tiffany’s relationships while abusing drugs versus while sober in prison. She mentions that Sarah, who she met in prison, was one of her first true friends. Discuss her friendship with Kayla. What differences do you see between the women?
7. In Chapter 38, Dr. Peters questions the reality of Tiffany’s story. Did you ever feel that she wasn’t being completely honest? Or did you find her to be a reliable narrator? Discuss how your reactions to her story shifted over the course of the book.
8. If you were making a movie of this book, would you keep the same structure and flashback technique? What moments would you highlight? What relationships would you focus on?
9. The book ends with Tiffany sharing her story with a group of recovering addicts, many whose stories are much like her own. What do you think about her second chance at life, and how she has chosen to share her message? If you got the chance to ask Tiffany one question, what would it be?
10. Are there any parts of Tiffany’s life, like her family or her relationship with Eliot, which you would have liked to hear more about? Why do you think she chose to focus specifically on her time in prison and the months leading up to her arrest?
11. Did you find the story impactful? How does Tiffany change the way you think about your own life story? Compare this book to other memoirs your group has read. Is it similar to any of them? Did you like it more or less than other books you’ve discussed?
12. Did Tiffany’s story about the tumultuous nature of addiction change any preconceptions that you might have had about drug abuse or the opioid crisis in the U.S.? Do you feel more empathetic or more distanced from those in similar situations to Tiffany’s after reading her story?