The Chaperone

Content Warning: This section of the guide contains discussion of racism.

Gather initial thoughts and broad opinions about the book.

1. Which aspects of Cora’s transformation from a conventional woman to a progressive thinker did you find most meaningful? How does her journey reflect broader social changes of the 1920s?

2. Jumping between different periods, from her childhood in the orphanage to her advocacy in later years, the narrative creates a complex portrait of Cora. How did this nonlinear structure affect your understanding of her character development? Did any particular timeline especially resonate with you?

3. The novel shares thematic elements with Edith Wharton’s The Age of Innocence, which Cora reads during her journey—both books explore societal constraints and personal desires. What similarities or differences did you notice between the two works?

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

1. What resonated with you about Cora’s search for her birth parents? Have you ever sought information about your family history or roots that changed your understanding of yourself?

2. Unconventional family arrangements feature prominently in the story, with Cora, Alan, Joseph, and their children living together under one roof. How does this family dynamic compare to your own experiences?

3. Louise’s fashion choices symbolize her rejection of traditional values while Cora initially clings to her corset. In what ways have you used clothing or other aspects of appearance to express your identity or values?

4. Cora reconciles with Alan after discovering his queer identity, creating an unconventional marriage that allows both to pursue happiness. Think about a time when you had to navigate a significant compromise. What influenced your decision?

5. Both Cora and Louise experience profound maternal rejection that shapes their lives in different ways. How did these portrayals affect you? What contributes to a healthy parent-child relationship in your experience?

6. Where have you felt the strongest sense of belonging in your life?

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

1. The 1920s depicted in the novel was a period of significant social change, particularly for women. Which cultural and political shifts of this period still resonate in today’s society?

2. When Cora attends an integrated theater in New York, she experiences a new cultural environment, different from segregated Wichita. How effectively does the novel address the racial discrimination of the period?

3. Attitudes toward sexuality evolve significantly across the decades portrayed in The Chaperone. In what ways have American views on sexual identity, agency, and consent changed since the periods depicted in the book?

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

1. What role do the contrasting settings of Wichita and New York City play in the novel? How do these locations function as more than mere backdrops?

2. Cora’s corset symbolizes constraint while Louise’s bob haircut represents liberation. Discuss how Moriarty uses these and other physical elements to reveal character development throughout the novel.

3. The concept of respectability runs throughout the novel. How do different characters define and relate to this idea? How does Cora’s relationship with respectability evolve throughout her life?

4. What irony does the title The Chaperone convey about Cora and Louise’s relationship?

5. Moriarty’s incorporation of Edith Wharton’s The Age of Innocence serves multiple purposes in the novel. How does this literary reference enhance the themes and character dynamics?

6. Moriarty reveals the outcomes of the characters’ lives decades after the main events of 1922. How does knowing these futures affect your interpretation of their earlier choices? Does this extended timeline enhance or diminish the story’s impact?

Encourage imaginative and creative connections to the book.

1. Describe a modern adaptation of The Chaperone. Which elements would remain relevant?

2. Write an alternate ending in which Cora decides to stay in New York with Louise rather than return to Wichita. Create a scene revealing how both women’s lives might have unfolded.

3. The novel ends with Cora feeling as though she’s on a train. Write a brief scene depicting her final reflections on the major turning points of her life.

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