1. In Fin and Lady’s world, what constitutes good parenting? What special wisdom do Fin and Lady share, despite their youth?

2. If you were to become the guardian of a young person in your family, who would be the best fit? What sort of life would you try to make for him or her?

3. How are Fin and Lady influenced by the memory of Hugo and Lydia? How is the siblings’ relationship affected by the fact that they have different mothers?

4. Which of Lady’s suitors were you rooting for? Was Fin an asset to Lady as she pursued love? What did her suitors teach him about the ideal man?

5. What are the similarities and differences between Tyler, Biffi, and Jack? How does each of them uniquely influence Lady’s life?

6. How does the 1960s time period affect the story line? Why is it appropriate for this tale to be set against a backdrop of social change in the face of tragedy?

7. What were your theories about who the narrator was? Is the narrator a sign of a new chapter for Fin, or is history repeating itself?

8. Discuss the irony of the names Lady and Fin (“end”). Do their names affect their sense of self?

9. What is Michelangelo’s appeal, in Lady’s eyes? How is he different from the other important men in her life, including her father?

10. Discuss Fin’s friendships with Phoebe and Donatella. What does he discover when he tries to find a love of his own?

11. What does Fin’s letter to Mabel, written from Capri (pages 219–20), reflect about this transitional time in his life?

12. On page 183, in the opening scene of the chapter “April Fool’s Day,” Fin asks himself, “If you’re the child someone never has to have, do you have to be an especially good one?” How would you respond to him? How is his life shaped by missing his mother?

13. Discuss the book’s three major locales --- rural Connecticut, Greenwich Village, and Capri --- and the ways in which they reflect the shifting personalities of the characters. Which locale would you prefer to call home? What does Fin and Lady’s globetrotting say about the meaning of home?

14. Cathleen Schine often creates characters who triumph in unconventional ways. Do Fin and Lady possess any of the traits you enjoyed in Schine’s previous novels?