Gather initial thoughts and broad opinions about the book.

1. What was your favorite part of the book and why?

2. Which character did you find the most compelling or engaging, and why? Were there any characters you wished received more attention in the narrative?

3. Have you read other books in the Winter Street series? If this was your first time, did the novel make you want to read the others? Why or why not?

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

1. Are there seasonal rituals in your own life that provide comfort or structure during difficult times? When have they helped or failed to help you?

2. How do you respond when life feels unresolved, or there are no clear answers? List some things that help you cope with those times.

3. What role does family play in your life? Do you have people you consider found family? What makes those relationships work?

4. Jennifer tries to cope independently before admitting she needs help. How comfortable are you asking for support when you are struggling? What makes it easier or harder for you?

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

1. Discuss how the novel portrays the holidays as emotionally charged events that amplify the characters’ joy and pain. How does contemporary culture pressure families to present unity and happiness during the holidays?

2. Considering both Mitzi and Jennifer, how does the novel comment on society’s attitudes toward female mental health, coping, and the stigma around substance use?

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

1. Analyze the book’s rotating narrative structure. How does hearing from multiple voices, including those outside the family, add to the story?

2. The novel takes place over the course of the weekend. How does this compressed time frame affect the pacing and tension?

3. How important is the setting in this novel? Give some examples of settings that play an important narrative or thematic role.

4. Analyze how, despite both Patrick and Bart being physically absent from the text, their presence looms large and affects the other each characters.

Encourage imaginative and creative connections to the book.

1. If you haven’t read the follow-up novel, Winter Storms, describe what you think will happen next for each of the characters. If you have read the next book, create an alternate timeline that takes the story in a new direction.

2. If you were to rewrite the novel from a single perspective, which character would you choose and why? How would that change or enhance the story?