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Discussion Questions
1. In the book's opening paragraph, Paul O'Rouke tells us that...

The mouth is a weird place: "not quite inside and not quite outside...but something in between...admitting access to an interior most people would rather not contemplate—where cancer starts, where the heart is broken, where the soul might just fail to turn up.

What kind of thematic concerns does this paragraph hint at for the book as a whole. Consider a later statement Paul makes that he is always "on the outside looking in."

2. How do the conditions of his patients' mouths affect, or perhaps simply correspond to, Paul's general view of humanity?

3. How would you describe Paul, his attitudes toward people and life, his relationship with women—in fact, his overall engagement in life? Betsy Convoy, his dental hygienist, accuses Paul of having a low opinion of humanity. Is that a fair assessment?

4. How has Paul's father's suicide affected his life as an adult?

5. What does baseball represent to Paul? Why is he such an avid Red Sox fan, and at the same time, why does he despair after the Sox finally win the World Series? SPOILER ALERT: Consider, too, the final pages of the book when Paul buys the Chicago Cubs cap...and agrees to play cricket with the Nepali kids in the street.

6. How would you describe Paul's relationships with women, primarily Samantha Santacroce and Connie Plotz. What does he want from them and from their families?

7. Paul tells us, "Everything is always something, but something—and here is the rub—could never be everything. What does he mean?

8. Why doesn't Paul believe in God? He tells us that he would have liked to: "Now there was something that could have been everything better than anything else." Why does he doubt?

9. What are the blog posts and Tweets in Paul's name about? How do they affect Paul? At first he is angry but becomes less and less so as the messages progress—why the change? Why do the posts offend Connie's Uncle Stuart? Are they antisemitic?

10. Who are the Ulms...and the Amalekites...and the Edomites? What is their relationship to the Hebrews in the Bible? The Ulms believe God has commanded them to doubt his existence. How is it possible to doubt the existence of God, who has revealed his existence to you?

11. What were Paul's reasons for not wanting to have children with Connie? SPOILER ALERT: He changes his mind toward the end of the book—why? What revelation does the pregnant patient elicit in Paul? Contrast his reaction to the expectant mother with his reaction to the marketing executive who just earlier had delayed treatment of his three cavities.

12. In what way is the billionaire hedge fund manager Pete Mercer a foil for Paul O'Rourke? How are they similar—and how are they different? SPOILER ALERT: Why does Mercer shoot himself after learning about Mirav Mendelsohn and Arthur Grant? How does Paul react o Mirav's story?

13. What is your reaction to the story of Arthur Grant and his desire to convert to Judaism? Consider how Paul O'Rouke's story parallels (to some degree) Grant's. What about Mirav—why after so many years has she returned to the fold?

14. Is this book religious...or anti-religious? Does Paul end up believing in God or not?

15. How has Paul changed by the end of the book? What do you predict for him?

(Questions by LitLovers. Please feel free to use them, online or off, with attribution. Thanks.)

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