1. Lucky endeavors to steal only from rich people and to give some of her profits to those in need. Why do you think the author chose to instill this practice in Lucky?

2. Early in the book, John says: “What matters in one moment, it doesn’t matter the next. Things that fall apart eventually come back together again. Everything passes. You can be sure of that” (p.27). What do you think of this advice? Why do you think John wanted Lucky to believe this?

3. The present-day timeline takes place in 2008. Why do you think the author chose this year for the story? How do you think the story would have differed if it were set today?

4. Were you surprised that Lucky didn’t reveal herself to Steph when they met at the open house? Why do you think she made this decision, and what do you think might have happened if she came clean?

5. Why do you think Lucky chose to approach Priscilla before seeking out Gloria? Do you think she really believed Priscilla would help her, or was she nervous to meet her mother? Who would you have gone to see first?

6. Lucky’s dog, Betty, is present in many parts of the book. What do you think is Betty’s significance in Lucky’s life?

7. Cary and Lucky both grew up with con artists for parents. Do you feel sympathy for Cary? Do you think he could have stopped stealing if he really wanted to?

8. In what ways does the author defy our ideas of criminals? Were any of your perceptions of criminals, particularly female criminals, challenged?

9. What do you make of Margaret Jean’s character? Does she bear any semblance to the book’s main characters?

10. Throughout the book, we see Lucky try to find normalcy in her life and then return to stealing. At the end, Lucky seems to have found some safety and stability. Do you think she is done stealing for good, or will the cycle start over again? Why?

11. Lucky views the lottery ticket as her escape from the way she has been living her life. Do you think receiving this large sum of money is the only way out, or can you imagine other ways she could have changed her path?

12. At the end of the book, it appears that Valerie is going to help Lucky avoid a prison sentence by having her testify against Priscilla. Do you agree with this resolution, or did you have a different vision for the consequences of Lucky’s actions?