1. When Pheby is moved to work in the house for Missus Delphina, she has a moment where she sits in Missus Delphina’s chair and uses her hairbrush. She looks in the mirror and muses “with a little rouge and a proper gown, I could fit in like a member of the family.” Why would Pheby want to fit in like a member of the family? In what ways did this scene foreshadow what would happen to Pheby in adulthood?

2. Why do you think Miss Sally took an interest in Pheby? In what ways do you think that her influence affected Pheby’s personality and outlook on her future predicaments?

3. When Pheby is serving dinner to Master Jacob and Missus Delphina, she is instructed to stand against the wall and pretend not to listen. She says, “Mama always said the way to keep peace with white folks was to be available and invisible at the same time.” How does this resonate with modern times, and what are the current sociopolitical implications of this?

4. Though Missus Delphina is aware that Pheby is Master Jacob’s daughter, she seems to take her wrath out on Pheby rather than her mother Ruth. Why do you think this is?

5. In the novel, children are portrayed oftentimes as either a source of joy for a family, a blessing, or a source of sorrow and tragedy. There are many scenes of mothers losing children in a myriad of ways. Discuss the sacrifices enslaved mothers had to make during this time in history.

6. Compare and contrast Pheby and Essex’s treatments as a man and woman within the institution of slavery. In what way was their different modes of survival different based on their genders?

7. What was it about Pheby that made the Jailer choose her? Even when he fathered children with other enslaved women, why do you think he chose to keep Pheby as the mistress of the jail?

8. Many times, Pheby wants Monroe to speak “properly” like her. Monroe is afraid to do so in case he is punished for it. She says to him: “People will judge you on the way that you speak.” To which Monroe responds: “Silver-head man did not like me speaking like white folk...told me to watch my uppity ways.” Discuss speaking styles such as improper or proper ways of speaking and what it means for Monroe and Pheby’s survival. In what ways does the way we talk or how we use language define us?

9. Pheby is anything but a damsel in distress. Where do you think her strength and resilience comes from? How do you think she endures her life with the Jailer in the parts of her story we don’t get to know?

10. Pheby describes the Jailer as looking at her with love in his eyes. Historians of slavery, particularly black feminist historians, have fiercely contested narratives (both fiction and nonfiction) that encourages such an interpretation, insisting that there could be no love between master and enslaved. Most see these “romantic” relationships as simply rape. What are your thoughts on their relationship? Could the Jailer, as Pheby’s oppressor, actually love her?

11. What were the dangers of Pheby’s daughters passing as white women in post-bellum society? Why do you think Birdie chose to stay with her mother and to not pass for white? Compare and contrast Birdie and Hester’s childhood and personalities and why they chose their own separate paths.