1. THE BOOK OF SOMEDAY opens with a quote from poet Antonio Machado: “Traveller there is no road, the way is made by walking.” How does this quote relate to what takes place in the novel? Why do you think the author chose it for the opening page?

2. When she’s a little girl, Olivia makes a list that contains dreams and wishes for her future. Some of the wishes on her list come true in very unexpected ways. Of the dreams for your life that you had when you were younger, what was the one that came true in a way that surprised you the most, and changed your life the most?

3. As the story unfolds, Livvi finds herself faced with incredibly difficult decisions. Choices that are life changing—for her, and for other people. Do you think Livvi’s commitments to the promises she made as a child are helping her in the choices she makes as an adult? Or are they hurting her?

4. Do you see Livvi as a woman who is strong and self-directed? Or a woman who’s allowing her past have too much of an influence on her future?

5. When Grace first appeared in the novel, what was your reaction to her? In Livvi’s place, what decision would you make about Grace?

6. When Sierra is talking about Livvi’s connection to Grace she says Livvi is just beginning her life and that Livvi’s responsibility is to herself and her own happiness. Do you agree?

7. At the end of the book, as Livvi is being offered the chance to make her sweetest dreams come true, should she let anything, even her feelings for Grace, stop her from claiming those dreams?

8. Do you think that someday Livvi might regret the choices she makes during the course of this novel?

9. At one point, Livvi asks Evelyn: “How does God decide who to bless and who to punish?” Would your answer to that question be different from the one Evelyn gives?

10. Among Livvi, Micah and AnnaLee, who did you relate to the most, and why?

11. If you were single, and David and Andrew were both available to you, which one would you choose? And what do you think your choice would say about you?

12. Do you think Andrew is a man doing his best to honor all of his commitments? Or is he a man who has found an intriguing way to avoid fully honoring any of them?

13. Does Andrew’s story suggest that there are times when it’s actually impossible to do the right thing?

14. Do you feel empathy or anger toward Andrew?

15. What are your feelings about David?

16. If you were to run into David five years after The Book of Someday ends, where do you think he would be in his life?

17. What do you think about Sierra’s theory of the “love goggles?” Do you agree that, at one time or another, every woman in the world has worn them?

18. Micah is described by one of the other characters as someone who gets off on making her own rules, going over the top, and being hell on wheels. How do these qualities affect your feelings about her? Do they make you want to put her in her place, or go out and have a cup of coffee with her?

19. Why do you think Micah gave away that anonymous ten thousand dollar gift? Was it openhearted generosity? Or a selfish attempt to buy a little bit of cosmic forgiveness?

20. Does knowing Micah’s background give you any sympathy for the way she lived her life and the person she turned out to be?

21. If life offered you what it offered Micah, the opportunity to be rich and famous, what would you be willing to sacrifice for that?

22. Some readers have said that they see quiet, shy AnnaLee as the strongest and most heroic of the women whose stories are told in this book. Do you agree or disagree…and why?

23. In your opinion, who was most responsible for what ultimately happened to AnnaLee?

24. If there were a way to bring Jack to trial for his failures, and you were on the jury, what would you convict him of? And what would you want his punishment to be?

25. At the heart of this novel is a mystery, a web of secrets. Secrets that ultimately cause the people keeping them to make incredible mistakes as they try to protect, and unwittingly betray, themselves and the people they love. Which secret in this book startled you the most? Was there one you thought was unforgivable?