Book Club Discussion Questions and Guide for The Windsor Affair by Melanie Benjamin

1. The novel alternates between Wallis Simpson and Queen Elizabeth. How did your sympathies shift between them, if at all?
2. The novel suggests that women, though excluded from formal power, wield influence behind the scenes. How do Wallis and Elizabeth each exercise power differently?
3. In what ways do class and social standing shape the characters' choices and limitations?
4. How does the book portray the tension between personal desire and public duty?
5. Jewelry plays a recurring symbolic role for Wallis. What do her jewels represent—security, identity, power, or something else?
6. The novel questions whether great love stories are real or constructed. How does this idea play out across the narrative?
7. How do public perception and gossip influence the characters' lives and decisions?
8. In what ways do both women actively shape their own narratives versus being defined by others?
9. The novel presents a speculative version of events (especially regarding the jewel theft and political intrigue). How did this blend of fact and fiction affect your reading experience?
10. Did the story change or deepen your understanding of the abdication crisis and its broader impact on the monarchy?
11. What are the similarities between the crisis of 1936 and the modern difficulties facing the royal family?

Unless otherwise stated, this discussion guide is reprinted with the permission of Delacorte Press. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.