August 27, 2025

In Conversation: Once Upon a Time in Dollywood

In partnership with our friends at Reading Group Choices, bring our August pick into conversation with these tailored discussion questions. Happy reading!

In Conversation: Once Upon a Time in Dollywood

In partnership with our friends at Reading Group Choices, bring our August pick into conversation with these tailored discussion questions. Happy reading!

Prepping for your August book club? We’ve got you covered with these 10 discussion questions developed by our friends at Reading Group Choices. Want more discussion question inspo? Learn more here!


1. In an interview, Ashley Jordan said, “Because we live in a world that demands perfection from women, expecting us to hold everything together, without complaint, while carrying the weight of everyone else’s needs, I wanted to create someone who eschews those expectations, and still gets to be seen, chosen, and loved.” How do you see Eve navigating societal expectations of perfection, particularly as a woman? Does her relationship to those expectations evolve throughout the story?

2. The book’s dedication includes the line, “To all the Black girls and women mistaken for difficult when they just needed to be seen.” How does Eve’s experience as a Black woman intersect with the societal pressures to be “perfect” or “acceptable”? What moments in the novel reveal the weight she carries? What helps her begin to let go of some of that weight?

3. Throughout the novel, there is an ongoing conversation about the tension between doing what you should do and what you want to do. Both Eve and Jamie feel bound by responsibilities to others that often conflict with their own desires. How do they each navigate and eventually balance these competing forces? What do you think the author is inviting the reader to reflect on through this theme?

4. Eve’s friendship with Maya provides something distinct from her romantic and familial relationships. What does this friendship offer her that her other relationships do not? Why do you think friendship becomes a safer, more nurturing space for growth? Does Jamie’s relationship with his brother serve a similar purpose?

5. Jamie’s relationship with his ex, Lucy, and his concern for his son are a painful part of his past and present that deeply effect his relationship with Eve. Were you surprised by the conversation he and Lucy were able to have at the end of the book in their empty house? What did you make of her self-awareness and acknowledgement of the pain she caused?

6. Therapy is portrayed in the novel not only as a tool for healing, but also as something something characters initially resist. Were you surprised by Eve’s or others’ hesitation around therapy? What societal or personal factors contribute to this resistance?

7. The book opens with a quote from Audre Lorde, “Pain is important: how we evade it, how we succumb to it, how we deal with it, how we transcend it.” How do both Eve and Jamie relate to the concept of pain? In what ways does pain shape their personal growth? Do you think their love story could exist without the pain they each experienced?

8. Eve processes her experiences and pain through her writing. What role does her creative process play in her healing? Were there any artistic choices she made that surprised you? Did she make any sacrifices for her art that surprised you? What inspired you about her journey as a writer?

9. The chapters alternate between Eve and Jamie’s points of view, and text messaging is used as an epistolary form of communication. How did the dual perspective shape your understanding of their inner lives and motivations? What might have been lost or gained if the novel had been told solely from Eve’s point of view? What did the text exchanges additionally reveal about Jamie and Eve’s communication styles and the evolution of their relationship? Have you read other books that use either of these structural choices? Did these formats enhance or detract from your reading experience?

10. Near the end of the book, Jamie quotes Audre Lorde, “Once we recognize what it is we’re feeling, once we recognize we can feel deeply, love deeply, can feel joy, then we will demand that all parts of our lives produce that kind of joy.” Eve recognizes the quote. How does this moment bring the novel full circle from its opening epigraph? In what ways have both Eve and Jamie transformed in order to be able to “demand joy” in their lives?

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