Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Who was your favorite Boleyn girl: Mary or Anne? Explain who you were rooting for and why.

2. Do you identify with the characters who struggle to resolve conflicting loyalties to their family at the cost of their wishes? Have you witnessed this in your own life?

3. Gregory depicts Henry VIII in this book as a vain, selfish, and spoiled tyrant. What do you think this portrayal serves? How accurate do you think it is?

4. Of what do you think Anne (and George) are guilty? How far do you think Anne went to get her prince? Point to the hints from the book that support your suspicions.

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. How realistic do you find the portrayal of how women operated under the strict patriarchal control of this era? What rebellion or autonomy do you see them achieving, and what can this tell us about contemporary gender roles?

2. What did you learn about the English Reformation from this book? Do you think Gregory is successful in showing the human rather than the philosophical side of this debate? Why or why not?

3. What questions do you think Gregory poses about systems of authority and obedience? Do you see any parallels between the absolute monarchy of Henry VIII and the present day?

4. While men make the decisions that rule public life, women oversee the inner world of emotions and desires. What evidence does Gregory provide to argue that women’s influence might have contributed as much, if not more, to these historic events?

Dive into the book’s structure, characters, themes, and symbolism.

1. What do you think of the novel’s suggestion that Anne’s ambition is her tragic flaw and that she sows the seeds of her downfall?

2. What does it add to the novel to make Mary and Anne foils? What perspective does George offer to the theme of Support and Rivalry Among Women?

3. Discuss the book’s opposition between the pageantry and excess of court and the more natural rhythms of life at Hever. How does Gregory use setting to highlight these two different worlds and their impact on characters? 

4. What do each of Mary’s lovers teach her—William Carey, Henry, and William Stafford? How does each man contribute to her maturation, growth, and character arc throughout the story?

5. What narrative techniques and symbolism does Gregory use to enhance the novel’s exploration of parenting and motherhood? Consider the focus on blood and lineage. How do these elements drive the central conflict and shape the characters' motivations and struggles?

6. Compare and contrast the key women in the novel—Mary, Anne, Queen Katherine, and Jane Seymour. How do they each function as rivals and foils to one another? You may additionally wish to discuss the role of Jane Parker.