Bookmarked by Reese’s Book Club

Episode: "Start Over, Stay Messy: A Conversation with Ashley Jordan"

Host: Danielle Robay

Guest: Ashley Jordan (author of Once Upon a Time in Dollywood)

Date: August 26, 2025

Overview

In this rich, candid episode of Bookmarked, host Danielle Robay sits down with Ashley Jordan, Reese's Book Club’s August pick author of Once Upon a Time in Dollywood. The conversation dives into building complex female protagonists, the messiness and joys of new beginnings, millennial culture, Black women’s communities, the aesthetics and meaning behind character choices, and the deep influence of pop culture and music—especially Dolly Parton, Beyoncé, and Lauryn Hill—on Jordan’s writing. Ashley also reveals her “manifesting” mindset, insight into literary mentorship, and her hopes for her next projects.

Key Discussion Points & Insights

1. The Story and Its Inspiration

• Summary of the novel (03:07):
  • Eve, a playwright, escapes a breakup and estrangement from her parents by fleeing to her grandmother's house in Tennessee “to write.”
  • She intends to be alone but gets involved with Jamie Gallagher (the “sunshiny single dad next door”).
  • It’s a classic “grumpy sunshine” romance—Eve is the grumpy one, Jamie the sunshine.
  • The undercurrent: Both characters have baggage and emotional exhaustion, but their journey is toward healing through vulnerability and learning to stop overthinking.
• Theme: “Start over, stay messy”—embracing imperfection as a path to growth.

2. Dedication and the Power of Black Womanhood

• Ashley reads her heartfelt dedication (06:06):
  • “To all the Black girls and women mistaken for difficult when they just needed to be seen. And to the village of Black women who not only raised me but lifted me. … I love you.”
• On the addition of “I love you”:
  • “It is the love of this village of women who made sure I made it to this point. So I thought it’s important to say, yeah, these are my grandma Hazels. And so thank you, I love you.” – Ashley Jordan (06:36)

3. Complex Female Protagonists & “Unlikable” Heroines

• Ashley argues for women’s right to be flawed:
  • “Why can’t she be unlikable? She’s going through something harrowing. … I think it’s really important that we let women be unlikable, especially when they have reason to. But even if they don’t have reason to be, let’s just be flawed and complicated and mean if we need to be.” (07:26)
• On writing Eve:
  • “She is really hurting and healing. The only way out of this is through, but she has to figure that out for herself.” – Ashley Jordan (08:18)

4. Generational, Cultural, and Millennial Context

• Eve’s millennial traits: Disney references, pop culture nostalgia, and a belief in fairy tales (09:33).
• On expectation vs. belief:
  • “You don’t have to believe you deserve it, you just have to expect it.” – Danielle Robay (10:30)
  • “Women are conditioned not to expect things, and so it’s hard to do that... But yes, I think that it’s powerful because then you put yourself in positions to get there.” – Ashley Jordan (10:49)

5. Pop Culture Infusion

• Eve as a blend of Molly Carter (Insecure) and Nora Durst (The Leftovers) (15:22)
• Ashley’s influences:
  • “She loves a Disney movie… she’s definitely a Disney millennial, and that part of her is definitely me.” – Ashley Jordan (09:33)
  • Frequent pop culture references, from Nene Leakes to Mad Men.

6. Character as Catharsis

• Ashley wrote from her own experiences of imposter syndrome and anxiety (16:05), especially during the pandemic:
  • “I kind of worked through that with her… when people started saying they liked it… I was just waiting for the other shoe to drop.”

7. Biblical and Symbolic Layering

• On naming Eve:
  • “She’s dealing with so much guilt, this desire to sort of carve her own path outside of what’s been expected of her. The way she walks away from her life is a bit of a fall from grace, in a way. But she’s not punished for it.” – Ashley Jordan (17:49)
• On Jamie:
  • “He’s almost like a biblical figure because he’s her road to healing… his gentleness with her and his grace with her felt almost like pastoral in a way. … While it wasn’t a conscious biblical reference, it ended up being one.” (18:28)

8. Motherhood and Identity

• Inciting incident: Eve’s miscarriage raises questions about what women really want, versus what’s expected or imposed by society (19:43).
• “That whole exploration of the idea of motherhood, I think, is super interesting because you get such a small window to do it. … Women have it hard.” – Ashley Jordan (21:20)

9. Self-Care During Creative Process

• Coping during the pandemic: writing and grad school as escapes from the heaviness of the world (23:25)
• On sleep: "No, I don't remember sleeping." – Ashley Jordan (24:10)

10. Journey to Publication & the Value of Community

• Experience as a 2023 Lit Up fellow gave Ashley mentorship (with Jasmine Guillory!) and a peer community (28:19).
• Manifestation works: “I manifested it... and next thing I know I got an email from Jasmine. So manifesting works.” – Ashley Jordan (28:48)

11. Music as Inspiration

• Music’s role:
  • “I can have music. I can’t have music with lyrics. So I usually just listen to, like, classical music or the Succession soundtrack. But I think music is, in general, just a very big inspiration.” – Ashley Jordan (32:19)
  • On fanfiction and Lemonade: “Albums are very much like books. You know, the songs are chapters. They tell a story. A really good album is a really good story.” (33:12)
  • Cranes in the Sky by Solange was a key song during editing.

12. Interactive Writing & Audience Consideration

• Influence of fanfiction:
  • “When you are writing fanfiction, you are posting usually one chapter at a time and getting feedback.” (34:29)
  • “I wrote with those sort of comments in mind, like, okay, don’t do this, because this will piss them off.” – Ashley Jordan

13. Manifesting and Next Projects

• Calling in: Hopes to write about Eve’s best friend Maya and her fiancée Siobhan:
  • “I would really love to write something about Eve’s best friend, Maya and her fiancée Siobhan. … We’ll see what happens.” (38:33)

Notable Quotes & Memorable Moments

On the Dedication:

• “To all the Black girls and women mistaken for difficult when they just needed to be seen. And to the village of Black women who not only raised me but lifted me. … I love you.” – Ashley Jordan (06:06)

On Writing Unlikable Heroines:

• “Let women be unlikable, especially when they have reason to. … Let’s just be flawed and complicated and mean if we need to be.” – Ashley Jordan (07:26)

On Fairy Tales and Manifesting:

• “You manifest your destiny. I really do believe that. And so, yes, wanting that fairy tale, even if you don’t feel like you deserve it. I think that’s how Eve ended up where she did.” – Ashley Jordan (10:03)

On the Biblical Allusion in Character Design:

• “He’s almost like a biblical figure because he’s her road to healing. … His gentleness with her and his grace with her felt almost like pastoral in a way.” – Ashley Jordan (18:28)

On Music & Storytelling:

• “Albums are very much like books. … the songs are chapters. They tell a story. A really good album is a really good story. So I think that I use them in that way. They inspired me to write.” – Ashley Jordan (33:12)

Important Segment Timestamps

• 03:07 – Ashley summarizes Once Upon a Time in Dollywood
• 06:06 – Ashley reads her book dedication
• 07:26 – Discussion on writing “unlikable” female characters
• 09:33 – Defining Eve as a millennial and nostalgia in the character
• 15:22 – TV characters that influenced Eve (and Ashley)
• 17:49 – Symbolism behind the protagonist’s name, “Eve”
• 19:43 – Why Ashley chose a miscarriage as the genesis of the novel
• 21:20 – Societal pressures and the “clock” of motherhood
• 28:19 – Ashley’s experience as a Lit Up fellow and mentorship with Jasmine Guillory
• 32:19 – Music’s role in Ashley’s writing (and Cranes in the Sky as a book theme song)
• 34:29 – Fanfiction roots and reader participation
• 38:33 – Hopes for next book, focused on Maya and Siobhan
• 39:34 – “Bookmarked This Week” – Ashley highlights the Black Romance Book Festival
• 40:11 – Speed Read rapid-fire book/literary Q&A

“Speed Read” Highlights

(40:11–41:53)

• Trope Ashley would ban: Enemies to lovers ("If I’m your enemy, we are not falling in love.”)
• Trope she'll defend: Grumpy sunshine and forced proximity
• Book she wishes she’d written: An American Marriage by Tayari Jones
• Favorite book to gift: A Love Song for Ricky Wilde by Tia Williams
• Dream library neighbors: Abby and Menace
• Favorite Dolly song to cry to: "I Will Always Love You"
• Favorite Beyoncé song to dance to: “Tyrant”
• Page-to-screen adaptation: Pride and Prejudice (2005)
• Book she wishes she could read again for the first time: Beloved by Toni Morrison
• Book that shaped her worldview: The Color Purple by Alice Walker

Tone & Style

• Warm, honest, deeply engaged with craft, keenly aware of both pop culture and literary tradition.
• Jordan speaks with humor, candid reflection, and an undercurrent of gratitude for her community—both personal and professional.

Closing Thoughts

This episode is a celebration of messy new beginnings, millennial nostalgia, literary community, and complex, flawed women—on and off the page. Ashley Jordan’s insights invite readers and writers alike to own their mess, claim space for vulnerability, and manifest their dreams—even (especially) when they seem audacious.

Selected and handpicked mentions, not directly content-related:

• Ashley’s favorite concerts and music influences, plus Breezy, pop-culture lit references kept the conversation lively.
• Rich commentary for both serious book lovers and fans of fun, inclusive conversations.

For more, connect on Instagram @ReesesBookClub, or check out Reese’s Book Club picks via Apple Books.