Hopeless

Gather initial thoughts and broad opinions about the book.

1. Discuss your overall impressions of Hopeless. Which were your favorite or least favorite aspects of the novel, and why?

2. How did your experience reading Hopeless compare with your experience reading the other Chestnut Springs novels? Discuss overlaps between this title and other titles in the series, including Reckless, Powerless, and Heartless.

3. Compare and contrast Hopeless to other contemporary romance novels. What narrative and thematic overlaps do you notice between Hopeless and titles like Annabel Monaghan’s Summer Romance or Nina Lacour’s Everything Leads to You?

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

1. How did you respond to Beau Eaton and Bailey Jansen’s fake engagement plan? Have you ever entered into a similarly unconventional relationship? What was its purpose and result, and how did the arrangement compare to Beau and Bailey’s?

2. Which aspects of Beau’s and Bailey’s relationships with Chestnut Springs were most surprising to you? Have you ever felt similarly trapped by an insular community? How did your response to these circumstances compare with the characters’ reactions?

3. Discuss Bailey’s response to the revelation that Beau owned The Railspur. Would you have responded in the same way? Why or why not? Have you ever been in a similar situation where you felt that someone else’s decisions had robbed you of your autonomy?

4. The novel explores the transformative power of love. How does love change Beau and Bailey in ways that resonate with your own romantic experience?

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

1. The novel tangentially explores the impact of war on the individual’s psyche via Beau’s point of view. How does the author represent combat and mental illness through Beau’s experience, and what commentary does the novel make about Beau’s healing journey?

2. At 22 years old, Bailey has never had sex. Discuss the social and cultural implications of Bailey’s virginity. How does she regard sex, and why? How does Silver use her experience to comment on a woman’s autonomy over her body?

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

1. Hopeless is written from Beau’s and Bailey’s alternating first-person points of view. Discuss the narrative and thematic effects of this choice. How do their perspectives relate to and inform one another?

2. Explore how Beau’s and Bailey’s characters fit into the larger Chestnut Springs community. Which aspects of their community life contrast with those of the other Chestnut Springs characters? Why is their relationship with the town so different from the other characters’?

3. Identify three symbols not mentioned in the guide and explore their significance. For example, what do the engagement ring, the trailer, and the stuffed horse represent, and how do they relate to the novel’s central plot points and themes?

4. Explore the relationship between Beau and Bailey’s past and present lives. How do the characters’ personal histories impact how they conduct themselves in the present? How does their relationship help them overcome these challenges?

5. Identify the romance tropes used in the novel and discuss their significance to Beau and Bailey’s romance. For example, how do the age gap, fake engagement, and forced proximity tropes intensify or complicate the lovers’ dynamic?

Encourage imaginative and creative connections to the book.

1. Imagine you are adapting Hopeless into a film. Who would you cast in the leading roles? Which artist would make the soundtrack? Which plot points would you add, omit, or alter to make the adaptation your own?

2. Imagine a different ending for the novel. What if Beau and Bailey didn’t move to the city? Would their relationship last inside the confines of Chestnut Springs? Why or why not? Sketch out an epilogue that charts this different path.