Gather initial thoughts and broad opinions about the book.

1. The central premise of the novel is a bed-and-breakfast designed as a “heartbreak retreat.” Did you find this concept to be an effective engine for the story, and how did it shape your expectations for the romance between Lou and Henry?

2. Ellen O’Clover’s work, including her young adult novel Seven Percent of Ro Devereux (2023), often centers on emotionally complex characters navigating major life changes. If you’ve read her other books, how does The Heartbreak Hotel compare? If this was your first, did it make you want to explore more of her writing?

3. Did you find the novel’s balance between a contemporary romance and a deeper exploration of grief, family trauma, and mental health to be successful? Where did this combination feel most powerful or challenging?

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

1. Lou’s idea of home transforms from a physical house to a feeling of belonging with people she trusts. What does the concept of “home” mean to you, and how has that definition changed over your life?

2. Where do you draw the line between caring for others and taking on a “caretaker” identity? Do you think Goldie’s criticisms of Lou’s tendency to fix others’ problems were fair?

3. The Comeback Inn is built on the idea that healing is a communal process. What are your thoughts on this approach to recovering from heartbreak? Which of the guests’ stories or interactions resonated with you the most?

4. Has a beloved song, story, or place ever changed meaning for you over time, similar to how Nate’s song “Purple Girl” evolved for Lou? How do we reclaim parts of our personal history that are tied to painful memories?

5. Throughout the story, Lou struggles with feeling like a fraud because she hasn’t passed her licensing exam. Have you ever felt a similar sense of “imposter syndrome” in your own life, and how did you navigate it?

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

1. What does Lou’s entrepreneurial pivot to the gig economy, by creating a short-term vacation rental, say about financial independence for women after a major life change? How does it reflect modern solutions to personal economic crises?

2. The narrative frames Lou’s tendency to prioritize others before herself as a direct result of growing up with a mother who dealt with untreated mental health issues. How does this psychological context add depth to the family dynamics and the sisters’ differing coping mechanisms?

3. How does the concept of a “heartbreak retreat” engage with broader cultural conversations about wellness and mental health? In what ways does the book challenge the idea that people should grieve or heal in private?

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

1. What is the significance of the house on Cedarcliff serving as the novel’s central symbol? How does its meaning shift for Lou, from a physical anchor to a place of healing, and for Henry, from a site of trauma to one of hope?

2. How do the parallel secrets kept by Lou (failing her exam) and Henry (his past with Joss and Molly) drive the central conflict of the story? Why was it important for both characters to have a significant vulnerability to overcome?

3. Consider the supporting cast, particularly Goldie and Mei. In what ways do these two characters represent the different kinds of support Lou needs to achieve her personal and professional goals?

4. What role does the “Purple Girl” song motif play in tracking Lou’s character arc? How does Henry’s rejection of this label help her move from an identity defined by Nate’s perception to one she creates for herself?

5. Henry’s journey from an isolated man consumed by grief to a partner capable of intimacy shares thematic elements with stories like Fredrik Backman’s A Man Called Ove (2012). How does the community at the Comeback Inn, particularly Lou, help draw him out of his self-imposed isolation?

6. In what ways do the recurring repairs Henry performs around the inn function as a metaphor for his own gradual emotional healing?

Encourage imaginative and creative connections to the book.

1. You’re tasked with designing a welcome package for a new guest arriving at the Comeback Inn. What three items would you include to set the tone for healing and self-care, and what would each item represent?

2. What kind of workshop or group activity would you design and lead at the Comeback Inn to help guests process heartbreak in a constructive way? What would be the main goal of your session?

3. You’ve been asked to write a new chapter for the book, told from the perspective of a former guest like Rashad or Grace, six months after their stay. What would their chapter reveal about the long-term impact of their time at the inn?