1. At the opening of the novel, Judith tells Teddy that he isn’t made for relationships. What do we learn about him early on that would give this statement validity?
2. How does Zoe view her father? What do you feel adolescent girls want most in a father?
3. At the Even Keel café on Nantucket, Zoe sets up rules for Teddy regarding women. What are they? What do these rules say, if anything, about how Zoe might want to be treated?
4. Teddy blames his mother for some terrible act that altered his life. And yet it gradually becomes evident that he admires her for several traits. What are they and why are they important to Teddy?
5. We come to see that the old family friend and caretaker, Frank, has an unrequited love. What advice does this cause him to give Teddy? There are other characters in the novel who possess love that has gone unrequited, as well as parts of themselves that have gone unfulfilled. Identify them and discuss what those unrequited or unfulfilled aspects are for each character.
6. How does Zoe express her pain? What other ways do people, young and old, use to express or bury that in life that most hurts them?
7. Why do you feel the author set this story on an island? Are there other kinds of islands in this novel?
8. Within this story, art plays a major role in healing and expressing one’s identity. The author’s own mother was a poet who, at the end of her life, suffered from Alzheimer’s. He has said that he and other family members were able to communicate with her through the use of poetry. What was there about art that allowed Teddy to “unlock” Kate’s memory? Do you feel art, and other forms of creative expression, might unlock parts of ourselves we don’t normally reach? Discuss how this could be applied to your life or the lives of those you love.
9. Kate initially becomes frustrated in trying to once again paint under Teddy’s guidance. What does her “handprint” signify to her and to Teddy? Imagine you are Teddy watching his mother paint again. Describe your emotions.
10. Liza has, herself, experienced tragedy. What does she say one must do with that pain in order to move on? Discuss the ways in which you or those you love have moved through difficult or tragic times. What or who helped you? What do you do with the pain?
11. Zoe takes a photograph that stuns Teddy when Liza shows it to him. What was the subject of the photo and what did it tell Teddy about the way his daughter sees herself?
12. Clearly, Zoe was keeping a secret from her parents. Would your child or grandchild be able to keep such a secret from you? What do we hide from those we love and why do we do it?
13. Gradually, the campaign back in California diminishes in importance in Teddy’s eyes, replaced by concerns about the three women he is dealing with on Nantucket. Discuss how each of these female characters alters him in some way. Are there women (or men) who have changed the way in which you see yourself and the world?
14. Why did Kate keep such a secret from Teddy? How did learning the truth change his view of his father and mother? How does he create a second chance for him and his mother? Discuss the importance of second chances in your own life and that of those you are close to.
15. Do you agree with Liza’s assessment that the Teddy we come to know at the end of the story would make a very different candidate should he ever decide to run again? How so?
16. The author has said he wanted to depict a character “rediscovering the artist in himself.” Do you believe there is an artist (however you interpret that) inside each of us?
17. What emotions does Kate’s final request of her son generate in you? How would you have responded?
18. Discuss Teddy’s decision in regard to his mother’s stunning last request and contrast his willingness to give up control and allow his mother her own choice. What is the author saying about love in this final act?