When the Wolf Comes Home

Content Warning: This section of the guide includes discussion of child death and child abuse.

Gather initial thoughts and broad opinions about the book.

1. Evaluate the protagonist of the novel, Jess. Did you find her relatable, sympathetic, or annoying? Explain why.

2. How do you feel about the novel’s ending? Did you wish that the boy had survived his father? If not, what did you appreciate about the way Cassidy chose to end it?

3. How does this book compare to Cassidy’s earlier novel, Mary: An Awakening of Terror (2022)? How are the two works different or similar?

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

1. How do you deal with estranged relationships? Do you think it is better to reconcile with someone who has distanced themselves from you, or do you think it is better to maintain your distance? How might you relate your answer to Jess’s relationship with Tommy?

2. Discuss your personal approach to fear. Are you the kind of person who engages fear head-on, or do you flee at the first sign of something that scares you? What is the novel’s position on how people should engage with their fears?

3. Have you ever been in a situation where you realized that your experience could lend insight to a younger person? Describe that situation and compare it to the way Jess tries to guide the boy’s understanding of himself.

4. Do you think people are doomed to inherit the flaws of their parents? Look to your own experience for an answer. If you agree, discuss what you have done to address the behavioral flaws you feel that you have inherited.

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

1. How does the novel tackle emotional abuse within the family unit? What do you think about the “found family” that Jess builds with Margie, Cookie, and the boy?

2. Jess’s emotional reality probes into the modern origins of anxiety. What are the factors that influence anxiety today? Do Jess’s backstory and character circumstances align with the factors you cited?

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

1. How does Cassidy use speculative elements to represent the emotional reality of fear? Compare this to Stephen King’s It (1986), which also features fear as a prominent motif. How does Cassidy’s representation of fear differ from King’s?

2. The novel makes frequent allusions to classical fairy tales, such as the Big Bad Wolf and Sleeping Beauty’s spindle. How do these allusions serve Cassidy’s themes? Why do you think he deploys them in a modern setting?

3. How does Cassidy use the supporting characters of the novel to drive the stakes surrounding Jess and the boy?

4. Is the boy’s character arc unfulfilled by the end of the novel? Justify your answer by describing the role he serves in the narrative.

Encourage imaginative and creative connections to the book.

1. During the novel, Jess and the boy go on a road trip. Put together a mixtape of songs that represent their experiences up until the point they meet Uncle Pepsi.

2. The novel ends with the implication that Jess now has the boy’s power. How do you think she integrates it into her life as she returns to the status quo from the start of the novel?

Need more conversation starters? Inspire your group with our Discussion Questions tool.