1. Despite the disasters she experienced at the beginning of the novel, what was good about Lucy’s life before she won the lottery? What were the best and worst changes that took place after she deposited the check?

2. How did Lucy’s parents influence her future? What explains the big difference in the way Lucy and Emma handle money?

3. Do you think Lucy would have stayed with Elliott if she hadn’t caught him with Naomi? How did her breakup, and her newfound wealth, change the way she thought about men?

4. How did your opinion of Mal and Drew shift throughout the novel? How do they affect Lucy in different ways?

5. What sustains Maisie and Lucy’s friendship? How does it compare to Hayden and Lucy’s friendship? What gives Maisie the strength to turn down Lucy’s money?

6. How does Lucy handle the secrecy of her new identity? Did she make the right choice in going underground? When are secrets helpful, and when are they harmful?

7. In the end, both Hayden and Emma realize how deeply they have hurt Lucy. What did it take for them to have a change of heart?

8. Discuss the novel’s title. How much of the success portrayed in Good Luck comes from sheer luck? How much of it depends on good choices? Which one—luck or choice—plays the bigger part in having a happy life?

9. Several of the novel’s characters, including Lucy’s mother, want to spend their resources easing the suffering of others. What determines whether someone will do charitable things with wealth, versus those who use it to serve their appetites for power?

10. What makes Whitney Gaskell’s heroines unique? How does Good Luck, along with the author’s other novels, capture the tragicomic truth about the demands of modern womanhood?