Gather initial thoughts and broad opinions about the book.

1. What was your initial reaction to the novel’s nonlinear structure? Did you find that jumping between timelines made the story more or less compelling? How did your understanding of the structure and its function change as you read?

2. Flournoy’s previous novel, The Turner House, focused on a large biological family. If you’ve read both novels, how did her exploration of a “chosen family” in The Wilderness compare? If this was your first time reading Flournoy, what other works would you compare this one to in its depiction of kinship?

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

1. The novel presents the friendship between the four main characters as a “chosen sisterhood” that is a source of immense support and a site of conflict. Reflect on the important friendships in your own life. In what ways do they function as a “fallback culture,” as Monique describes it?

2. Monique writes about her “Scared and Stingy years” (200), a period when she prioritized professional goals over personal relationships. Can you relate to this idea of having distinct personal “eras”? How has your own perspective on balancing ambition and relationships evolved over time?

3. Desiree’s search for a “livable life” leads her to a vision of quiet contentment rather than grand ambition. What does a “livable life” mean to you personally? How has your definition of it been shaped by your own experiences?

4. January’s experience with postpartum depression and pelvic organ prolapse is depicted with raw honesty. How did her flight to Nakia’s house for refuge speak to you about the importance of having a safe place to land during a crisis?

5. The characters often feel a deep connection to the cities they live in. Think about a place that has been significant in your own life. How has that place shaped your identity or your sense of belonging?

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

1. How did grounding the story in real-world events like the 2008 financial crisis, gentrification, and 2020 protests against police brutality affect your reading experience? In what ways do the fictional “Bunker Hill Uprisings” feel reflective of current events and predictive of future events? How does Flournoy use these events to create a deeper sociopolitical commentary?

2. Monique’s experience on the university committee highlights the sanitization of history, specifically regarding enslavement. Where else do you see this kind of historical revisionism happening in society today? What does the novel suggest about the importance of confronting uncomfortable truths?

3. Nolan Richard’s plan to seek assisted suicide brings up the complex “right-to-die” debate. What different perspectives on autonomy and end-of-life care does the novel present through the conflict between Desiree Richard and Danielle Joyner? How did this storyline make you think about the ethical and emotional questions surrounding this issue?

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

1. The novel’s title, The Wilderness, has metaphoric meaning. What does this “wilderness” represent for each of the four main characters? How do their journeys through “the wilderness” differ, and what tools do they use to survive?

2. Monique’s blog, “Black in the Stacks,” functions as a distinct narrative form within the novel. What role do these posts play in the overall story? How does Monique’s public voice as a writer contrast with her private struggles and interactions with her friends? How would the novel differ without them?

3. The deep, complex friendship between the four women is central to the novel. How does this depiction compare to other famous literary friendships, such as in Toni Morrison’s Sula? What makes the bond in The Wilderness feel unique or particularly resonant?

4. Physical spaces are highly symbolic, from Nakia’s Safe House Café to the “Miss April Houses.” Choose one significant location from the book and explore what this space reveals about the characters who inhabit it and the societal forces at play.

5. A central tension exists between private memory and public narrative, especially after Nakia’s death. How do the surviving friends attempt to reclaim Nakia’s story from the media? What does the novel ultimately say about who gets to control a person’s legacy?

Encourage imaginative and creative connections to the book.

1. Design a small zine or a social media graphic that explains Monique’s concept of a “fallback culture.” What images, text, or anecdotes would you use to capture the essence of what it means to be a “fallback” friend?

2. Create a memorial for Nakia that truly captures who she was, beyond the “Local Restaurateur” label. What form would this memorial take, and how would its elements honor her spirit, her work, and her relationships?

3. Step into the role of one of the surviving friends—Desiree, January Wells, or Monique L.—five years after the novel ends. Write a short journal entry from the perspective of this character. What does your life look like now, and how has Nakia’s memory continued to shape your choices and relationships?