1. “Her whole life she’s been peering at everything she’s ever wanted from the outside.” Why do you think Taylor has felt like an outsider her whole life? What appealed to her about Boston, and about Vivian in particular? How do you think Taylor grew over the course of the novel, and what did she learn from her experience with the Knox?

2. The Knox is very much a character in the story, with its own opinions and chapters. What did you make of its voice? How did having the Knox’s perspective add to the story?

3. “Do you know what secrets really are, Vivian? They’re chips to bargain with; they’re ownership.” Do you agree with Peter’s statement about secrets? What role did secrets play in the lives of the characters, and how did they shape the events of the novel? Which reveal surprised you the most?

4. The novel contrasts two women from very different social backgrounds: Vivian, the privileged Bostonian, and Taylor, the ambitious newcomer. How do their experiences mirror or challenge each other? What do their perspectives reveal about power, class and belonging?

5. The author drew inspiration from Boston’s true connection to the opium trade. How does that historical detail shape your reading of the novel? Does it change your perspective on the Knox or the characters’ motivations and decisions?

6. Both women’s relationships with their mothers shape their choices and outlooks on life. How do these mother-daughter connections (or absences) echo throughout the story?

7. The story is told across multiple timelines and perspectives. How did this narrative structure affect your experience as a reader? Did it heighten suspense or shift your sympathies?

8. There are many minor characters in the novel who play important roles in shaping the story. Which of these characters were you most drawn to, and why? How did their actions or perspectives influence your understanding of the main characters or the themes of the book?

9. What do you think draws people to organizations like the Knox? Ambition, curiosity, legacy or something else? Did your opinion of the society evolve as the story unfolded? If you were extended an invitation to a secret society in your own town or city, would you accept it? Why or why not?