24 Book Club Discussion Questions for Once Upon a Time in Dollywood by Ashley Jordan

If you’re a book club organizer on Bookum, reader, or discussion leader looking for thoughtful and engaging questions about Once Upon a Time in Dollywood by Ashley Jordan, this guide is designed to help you spark meaningful conversations around themes of healing, love, and starting over. These questions are perfect for contemporary romance and women’s fiction readers seeking to explore character development, relationship dynamics, and the emotional layers of the story.

Characters, Relationships & Emotional Truths

1 - How does Eve Ambroise’s choice to leave her old life behind resonate with readers facing personal reinvention?

2 - What challenges does Jamie Gallagher face as a single dad, and how does that shape your understanding of his character?

3 - How do Eve and Jamie’s past traumas influence the way they connect and build trust?

4 - In what ways do the townspeople and community setting act as both support and obstacle for Eve?

5 - Does the dynamic between Eve and Jamie feel authentic for a second-chance romance? Why or why not?

Plot, Stakes & Real-World Parallels

6 - How does the Tennessee mountain setting enhance the emotional tone of the story?

7 - What are the key turning points in Eve’s journey toward healing and self-discovery?

8 - How realistically does the book portray the complexity of starting over after difficult relationships?

9 - How do themes of family, custody, and personal freedom intersect through Jamie’s storyline?

10 - Were there moments in the plot that surprised you or challenged typical romance conventions?

Conflict, Heartache & Growth

11 - When does Eve’s vulnerability become most apparent, and how does this impact reader empathy?

12 - How does Jamie manage balancing his responsibilities as a father with his budding romance?

13 - What internal conflicts prevent the characters from fully opening up to each other?

14 - Which character’s personal growth felt the most compelling, and what lessons can readers draw from it?

15 - Is the resolution of the story satisfying and believable within the context of the characters’ struggles?

Big Themes & Social Commentary

16 - How does Once Upon a Time in Dollywood explore themes of forgiveness, grief, and self-care?

17 - What insights does the book offer about the importance of boundaries and personal healing?

18 - How does community, both biological and chosen, influence the characters’ paths?

19 - In what ways does the story address the challenge of trusting love again after loss?

20 - What metaphors or imagery related to the natural setting stood out and deepened your understanding of the themes?

Final Reflection & Reader Engagement

21 - After finishing the book, how hopeful do you feel about Eve and Jamie’s future together?

22 - How does this novel compare to other contemporary romance or women’s fiction you’ve read recently?

23 - Would you recommend Once Upon a Time in Dollywood to someone seeking stories about healing and new beginnings? Why?

24 - What is one memorable quote or moment from the book that will stick with you?

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