Gather initial thoughts and broad opinions about the book.

1. Were you surprised by the reveal that Harley’s boyfriend was Jesse/Hutch, and not actually Cooper? Were there any other plot twists that stood out to you?

2. Which narrator did you find most compelling? Why?

3. How does this book compare to other thrillers by Freida McFadden, such as The Housemaid or The Boyfriend? What similarities or differences do you notice?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. When the novel opens, Debbie feels her life is a bit stagnant and boring. Have you ever felt stalled in your personal life or career? What steps did you take to change your circumstances?

2. Harley longs to be in a stable relationship, but struggles to find love in a healthy way. Have you ever had difficulties with dating and/or commitment? How did you navigate these issues? 

3. Debbie and Cooper keep long-standing secrets from one another. Have you ever kept a secret from someone important in your life, or realized someone was hiding something from you? How did your experience compare to Debbie and Cooper’s?

4. Readers of the Dear Debbie column write to Debbie for advice on their personal dilemmas. Have you ever written to an advice column yourself, or been a regular reader of one? If yes, how does your experience with advice columns reflect or diverge from the experiences of Debbie’s readers? If not, to where/whom do you typically turn for good advice?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. How does the book reflect contemporary conversations about misogyny and rape culture?

2. Discuss the influence of modern technology on the action of the novel. How would the novel be different if it took place 100 years earlier? How does the novel expose some of the advantages and pitfalls of modern tech?

3. Explore the novel’s depiction of modern romantic relationships. How is navigating romance different or similar for teens like Lexi and adults like Harley?

Dive into the book’s structure, characters, themes, and symbolism.

1. Discuss the structure of the novel. What is the effect of the novel’s short chapters and three distinct narrators? How does this structure impact the novel’s plot, characterization, and/or Themes?

2. How does Debbie’s character develop over the course of the novel? How has she changed—or failed to change—by the novel’s end?

3. Explore the significance of the novel’s setting in the suburbs of Boston. How is the setting described? What is its wider significance in the text?

4. Discuss the role of anger in the novel. How do different characters experience or weaponize anger? What does the novel suggest about the nature and dangers of anger?

5. Analyze how the novel utilizes or subverts common tropes of the thriller genre, or more specifically, the domestic thriller. How does Dear Debbie conform to or diverge from generic conventions?

Encourage imaginative and creative connections to the book.

1. If you were adapting Dear Debbie into a movie or television series, who would you cast in the roles of Debbie, Cooper, and Harley?

2. Do you think that Debbie will return to her violent ways? Imagine what might come next for Debbie and share your ideas.

3. Choose one of the Dear Debbie draft chapters, and write your own response to the reader. What advice would you give?