1. What is the significance of the title? Who in the book is lost?
2. What is the distinction between being lost and being missing?
3. What is Caroline searching for?
4. How does Ellie’s disappearance affect the relationship between Madeline and Caroline?
5. How is setting important in How to Be Lost? Where does Caroline feel most comfortable, and why?
6. What role does alcohol play in the novel? How does it initiate, complicate, or smooth out circumstances?
7. In what way do Winnie and Peggy function as surrogate sisters for Caroline?
8. There are a number of mothers in How to Be Lost: Isabelle, Sarah, Winnie, Madeline, and Mrs. Lake. Discuss these different images of motherhood. Are any of these mothers revered? Criticized? What role do these women play in protecting their children and offering them a sense of the world?
9. Bernard tells Agnes that “There’s always another chance to take what you deserve.” Do you think that Bernard’s belief is always possible? Do any other characters in the novel seem to hold a similar view?
10. Roxie utters only a few words in the novel, but she leaves a strong impression on Caroline. What role does Roxie play in Caroline’s journey? What sort of revelations do Roxie and Olivia provide for Caroline?
11. Compare and contrast Charlene with Agnes. Both are lost to their families but there is a distinct difference—the element of choice. Discuss these two women and how the element of choice affects their separate lives.
12. At the beginning of the novel, Caroline attempts to avoid going home to her mother’s condo in New York for the holiday, but by the book’s end, she feels at home there. What brings about this change? How is home defined for her in the end?
13. Ward uses multiple perspectives—Caroline’s first-person account, Agnes’s letters, and a third-person, omniscient narrator—to tell this story. How did this structure affect the story and your understanding of it? What is the role of the reader in the unraveling of the mystery of the Winters family?
14. If you have read Ward’s previous novel, Sleep Toward Heaven, do you see any common themes or elements in How to Be Lost ?