1. What were your first impressions of Peter and Rebecca? What aspects of their marriage were presented in the opening scenes as they observed a traffic accident, attended a party, and went to bed?

2. Ethan’s nickname originated as a reference to his parents’ unplanned parenthood so late in life. Did the label shape his impressions of himself, or were his problems inevitable? Did his parents and his sisters (from eldest to youngest: Rosemary, Julianne, Rebecca) expect too little of him?

3. How did Peter’s and Rebecca’s families influence them well into adulthood? What did Peter and Rebecca offer each other when they were first dating? How did the basis for their attraction change over the years?

4. What is Peter’s role in the lives of the artists he represents, beyond securing a high price for their work? What intangible benefits does he sell to his buyers? What makes him good at his job?

5. How does the concept of leverage play out in By Nightfall? Who are the novel’s most vulnerable and most powerful characters?

6. How does Uta’s philosophy of life different from Peter’s? How does she balance the reality of her role as a businesswoman with the intuitive and emotional aspects of her profession? For her, is there any distinction between her profession and her passions?

7. What does By Nightfall say about making art, and marketing it? How does Peter’s work compare to Rebecca’s in shaping the futures of creative individuals? What new freedoms and challenges does twenty-first-century American culture bring to creative fields, and to our personal lives?

8. Ultimately, what is Bea blaming her father for? Is she right to blame him? What does he teach her to expect from men? When Rebecca worries about her daughter, what fears is she also expressing about her own future?

9. What purposes does sex serve for the novel’s primary characters? How did sexuality shape Rebecca’s self-esteem before and after she was married? What longings is Peter responding to at the moment of the kiss? For Mizzy, does sex present anything more than an opportunity to be manipulative?

10. How does the purpose of marriage evolve throughout Peter and Rebecca’s life together? What reasons do they have for remaining married after Bea has left for college? What identity did marriage create for them in their careers?

11. Michael Cunningham provides us with Peter’s thoughts throughout By Nightfall. How would the novel have unfolded if it had been told from Rebecca’s point of view instead?

12. Is Mizzy a victim or a victimizer, or both? If he were your little brother, would you respond to him the way Rebecca does?

13. The novel concludes with the beginning of an honest dialogue. How much of Peter and Rebecca’s previous talks had been truthful? Had they been honest with themselves? What predictions do you have for the closing line’s conversation and its aftermath?

14. Discuss the novel’s title: What symbolic nightfall exists in the characters’ lives? How does it apply to the concept of aging and other transitions that may seem difficult to navigate in the “dark”?

15. Through his fiction, what has Cunningham shown us about the nature of love and longing? What new facets are revealed in By Nightfall? What role do artists (literary, visual, and otherwise) play in his storylines?