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Reading Group Guide

Discussion Questions


1. How did Cassia’s newly acquired wealth play a role in her seemingly newfound resentment toward Edward? Were her feelings new or did the money simply bring to the surface emotions she had suppressed for years?

2. After Edward first announced to his parents that he and Cassia, unbeknownst to her, were engaged, should she have prolonged her trip in order to express her feelings, concerns, and doubts about their relationship? Or do you think it was her duty to stand by and support him in his endeavors?

3. What is your reaction to Cecily and Benedict remaining married even after he opens up to her about his homosexuality? Why was it so important to Cecily and Benedict to appear as a happily married couple, even after they both knew that it would not work out? What would their alternatives have been? What is the reaction that most of the characters have toward homosexuality? Is it much different than today?

4. What role did wealth and status play in this book?

5. When Edward decided to take on an assistant without consulting or discussing the issue with his wife, did Cassia have a right to be angry after all of the things she had taken upon herself to experience and enjoy? Why?

6. Why did Edward feel that he was right in demanding that Cassia move to Scotland with him in order to return to medical school? Why was Cassia right in defying his wishes?

7. How were unwed pregnant women treated in the book?

8. How did Cassia’s unhappiness in her own life play a role in her work at the clinics? How did the stress of an unfulfilled life and an unhappy marriage make her more sympathetic toward the women she treated?

9. Social failure was, to many in the book, absolutely unacceptable. Which characters do you think sacrificed the most, and in what way, for the sake of their reputations?

10. What significance did Cassia’s decision to skip her Friday morning ritual with her children in order to tour a hospital for her own benefit have? Was this the start of a dangerous trend?

11. Each of the three leading ladies (Cassia, Cecily, and Edwina) made life-changing discoveries about themselves or their lives. In what ways were they the same? In what ways did they differ?

12. Despite the time period in which Windfall is set, what statement do you think Vincenzi was trying to make about feminism?

13. Why do you think Vincenzi decided to foreshadow Cassia’s story with that of the King’s? What impact does this have on the rest of the story?

14. How did the two incidents involving blackmail differ (first with Benedict and his former lover and second with Rollo Gresham and Harry)? Which, if either, seemed more acceptable and why?

15. Why did Cassia blame Harry for the misfortunes that befell her after receiving her inheritance? Why was she right or wrong in her conviction?

16. How did Cassia’s stubbornness at the end of the book make you feel? Was she protecting herself from making another life-altering decision that might upset her for the rest of her life? Or was she simply being difficult?

17. How did Cassia’s relationship with Edward change throughout the book? Did it get better or worse over time?

by Penny Vincenzi

  • Publication Date: October 1, 2009
  • Hardcover: 624 pages
  • Publisher: Overlook Hardcover
  • ISBN-10: 1590202473
  • ISBN-13: 9781590202470