1. Lisa Wingate brings to life stories from actual "Lost Friends" advertisements that appeared in Southern newspapers after the Civil War, as newly freed slaves desperately searched for loved ones who had been sold away. Had you heard of the real "Lost Friends" ads before? What did you think of the words written so long ago? What did you learn about the Reconstruction era through this novel?

2. The Book of Lost Friends is a story of remarkable women who built legacies we benefit from today. There are many women from the past, like Hannie, who do not often make it into our history books. Who is one woman from history that you greatly admire and think that the world should know more about?

3. What lessons does Benny learn from her students? Do you think her students change her?

4. The town of Augustine is controlled by a powerful family with secrets. Have you ever learned of a secret in your own or someone else’s family? What was the reason for it, and what were the results of it coming out?

5. Hannie, Juneau Jane, and Lavinia are an unlikely trio when they start on their quest. How does their journey shape them as they come of age? How do Hannie and Juneau grow during their quest? What does each learn from the other?

6. Elam Salter is a character with a larger-than-life reputation. What is his role in the story? Why does Hannie find it hard to trust him?

7. Symbolism is used in this novel in a number of ways, including: the single ladybug, Hannie’s blue beads, and the church where the main characters hide. What do you think these symbols mean? Did you notice any other symbolism in the novel?

8. In what ways do Benny and Nathan help each other move forward?

9. What do you think Benny is going to do at the end of the novel?

10. A volunteer at the Historic New Orleans Collection sparked the idea for this novel when she wrote to Lisa about the Lost Friends database. Why do you think history, particularly that preserved in the voices of those who lived the experience, matters?

11. Visit the Lost Friends database. Choose one ad to share with another member of your book club.