1. Discuss how racism affects both women and their families, such as when Ruby goes stocking shopping with Aunt Marie or how she’s treated at the House of Magdalene. Would these instances be surprising today? Why or why not?

2. When Eleanor meets William’s family, she describes it as being “a room filled with white-faced Negroes.” How does colorism play out in the novel for both Ruby and Eleanor?

3. Both Ruby and Eleanor have mentors: Ruby with Mrs. Thomas and Eleanor with Mrs. Porter. How do these women support their mentees, and how would the story have played out if they weren’t a part of Ruby and Eleanor’s lives?

4. Ruby and Eleanor fall in love with men who are off limits and forbidden. Shimmy is Jewish and William is upper class. How do these conflicts affect their relationships and shape each woman’s decisions throughout the novel?

5. William and Shimmy may seem like opposites, but how are they similar? What prejudices do both men face?

6. Motherhood is a strong theme throughout the book. How do the actions of Rose, Eleanor’s mother-in-law, and Mrs. Shapiro, Shimmy’s mother, affect Eleanor and Ruby? Would you consider their behavior cruel or justified?

7. William and Shimmy propose upon hearing of their girlfriend’s pregnancies. Ruby says to Shimmy, “Your mother will crush our love. The world will stomp out our fire.” Could Eleanor have also said this to William? Why or why not?

8. Consider the other young women and the nuns at the House of Magdalene. How does religion bring shame to what happened to them? How does this stigma of shame and unwed mothers affect the women, and does it still exist today?

9. Despite hardships, the book carries a theme of second chances and hope. How do Ruby and Eleanor find hope, even in their darkest moments? What keeps them going?

10. Discuss the last chapter of the novel, where Ruby and Eleanor meet in person. How did it make you feel? If the book continued, would you want the women to connect over what happened or remain simple acquaintances?