Once Upon a Time in Dollywood Summary, Characters and Themes

Once Upon a Time in Dollywood by Ashley Jordan follows Eve, a playwright whose life has been reshaped by grief, loss, and the weight of decisions made for her long before she understood their impact. 

After a painful breakup and a devastating history of miscarriages, she retreats to her late grandmother’s cabin in Tennessee, hoping to find air, clarity, and distance from the people who keep telling her how to heal. There she meets Jamie, a single father carrying his own wounds. Their unexpected connection forces both of them to confront the past, question their choices, and imagine futures they never believed they could claim.

Summary

Eve’s story begins at a breaking point. After a third failed pregnancy and a suffocating therapy session with her fiancé Leo, she walks out, unable to handle his anxious concern or her own waves of panic. Instead of returning to him, she goes to Maya, her closest friend, who offers support without pressure. Eve admits she feels trapped in New York and exhausted by trying to be the version of herself everyone expects. Searching for an escape that still gives her structure, she decides to go to her late grandmother Hazel’s cabin in Gatlinburg, Tennessee, a place tied to secrets she has never resolved.

When Eve arrives at her parents’ home to get the cabin keys, Leo is waiting. Her mother fusses, her father tries to stay upbeat, and both assume this trip is a writing retreat. But when Eve announces she plans to leave the next morning and doesn’t want Leo to visit, everyone reacts with questions and alarm. Feeling cornered, Eve impulsively ends the engagement in the middle of dinner and leaves with the keys, devastated but determined.

Meanwhile in Nashville, Jamie is in the final stretch of a custody hearing with his ex, Lucy. The judge grants him primary physical custody of their son, Jack, while Lucy receives weekends. Relieved but worn down, Jamie tries to be gracious as he drops Jack off at Lucy’s house, even as her fiancé’s presence stings. He tells Lucy he plans to spend some time at his own cabin in Gatlinburg to rest.

Eve reaches Hazel’s quiet mountain cabin and is overwhelmed by memories of being sent there at seventeen to hide her pregnancy. She settles into the solitude until she encounters a man near the property and assumes he’s trespassing. The misunderstanding clears when they realize they both knew Hazel. He is Jamie, the neighbor who has been looking after the place. 

Though Eve is wary, Jamie brings groceries and a small cake to welcome her, showing gentle, practical kindness she doesn’t quite know how to accept.

Days later, Eve runs into Jamie in town, then experiences a severe panic attack in the parking lot. Jamie recognizes what’s happening from helping Jack through similar episodes and steadies her with calm, clear guidance. Grateful yet embarrassed, Eve goes with him to breakfast and lets him drive her home. 

Their rapport grows, but when he mentions his son, Eve is jolted by memories of the child she was forced to give up. She retreats emotionally, yet later she chooses to accept his dinner invitation.

Their evening together becomes a turning point. In his small cabin, Eve learns about his life, his heartbreak, and his quiet resilience. He learns about her work as a playwright. 

They talk, drink, listen to music, and fall asleep side by side. In the morning, he leaves her a practical note before heading to Nashville to pick up Jack, which leaves her feeling rejected even though she knows his gentleness is genuine.

As days pass, Eve settles into a routine of writing and trying to make sense of her grief. When she receives career-changing news that a major theater is interested in her play, she spirals with pressure and self-doubt. 

A call to her parents only worsens things, especially when she confronts them about the choices they forced on her at seventeen. Her mother avoids responsibility, and her father insists they did what was best. Shaken, Eve drunkenly calls Leo, whose angry response leaves her even more hollow.

When Jamie returns to Gatlinburg, Eve cooks him dinner as a peace offering. Under the glow of synchronous fireflies, they speak honestly about their lives, their losses, and their fears. 

Their connection deepens, and they begin a relationship marked by trust, desire, and a slow healing neither expected. Over time, Eve becomes part of Jamie’s routine. She writes, works remotely, and spends weekends with him. He teaches her the rhythms of mountain life, and she encourages him to consider returning to school. They even experiment with long-distance intimacy when he’s in Nashville with Jack.

But their closeness becomes complicated when Jamie invites her to Thanksgiving in Nashville and suggests Jack meet her. 

Terrified of facing a child, and still burdened by the loss of her own, Eve pulls away. Their argument exposes every limitation and fear between them. Jamie refuses to be compartmentalized, and Eve cannot explain her hurt without revealing too much. They part in pain and silence.

On Thanksgiving, Jamie hosts a crowded, chaotic family dinner and learns Lucy is expecting a new baby with her fiancé. The news shakes him, but his family comforts him. That night, Eve arrives unexpectedly with flowers. They talk quietly, reconnecting with tenderness. 

He introduces her to Jack, and she instinctively steps into a gentle role in the boy’s day. The experience softens her fear.

That night, Eve tells Jamie the truth about her miscarriages and the grief that pushed her to run. He tells her she deserves joy and steadiness and says he and Jack could be hers if she wants them. 

They make a plan: Christmas in New York, New Year’s in Paris, and a future that belongs to both of them.

Over the next weeks, Eve becomes part of Jamie’s Nashville life, bonding with his family and helping Jack navigate the changes around him. Decorating a Christmas tree together, Eve realizes she no longer feels like she’s hiding from her life. She is choosing it. 

And as she looks ahead to Dollywood, Paris, and New York, she steps fully into the possibility of a life shaped by her own choices rather than the expectations of others.

Characters

Eve

Eve is the emotional center of Once Upon a Time in Dollywood, a woman shaped by grief she has carried privately for years. Her life in New York has been built around control, routine, and the silence she learned as a pregnant teenager whose choices were taken from her. 

This history fuels her fear of vulnerability, her struggle with self-worth, and her habit of withdrawing when intimacy feels too close. At the start, she is overwhelmed by loss, shame, and a long-standing belief that she must endure pain quietly. Her retreat to Hazel’s cabin becomes an unplanned confrontation with the pieces of herself she has hidden. 

Through her interactions with Jamie and Jack, she discovers unexpected strengths: tenderness, resilience, and the courage to speak truths she once buried. Her arc is defined by learning to accept comfort without guilt, claim a future not dictated by fear, and trust that her desires are allowed to matter.

Jamie

Jamie is gentle, steady, and sometimes uncertain of his own worth, shaped by betrayal from both his ex-partner and his mother. 

His life revolves around fatherhood, and much of his identity has narrowed into being Jack’s protector and provider. Beneath this devotion is a man who feels overlooked, exhausted, and unsure where he fits beyond the role he has fulfilled for eight years. His kindness toward Eve arises from instinct rather than calculation; he sees her distress and responds with care because that is how he navigates the world. Yet he also struggles with insecurity and fear of abandonment. 

When Eve pushes him away, his past wounds resurface, making him defensive. Jamie’s journey is about rediscovering his own ambitions, reclaiming pieces of himself he sacrificed, and recognizing that he deserves a partner who chooses him openly. His love for Eve becomes a catalyst for imagining a life defined by possibility rather than limitation.

Jack

Jack is a bright, curious child whose emotional intelligence reveals itself through direct questions and earnest attempts to understand the adults around him. He has already lived through parental separation, instability, and shifting households, which makes him perceptive to change and sensitive to being sidelined. 

Jack’s interactions with Eve show how easily he accepts her presence once he senses her authenticity. He asks questions not to test boundaries but to build connection. His behavior, from hoarding marshmallows to proudly showing Eve his room, reflects a child trying to create order in a world that keeps rearranging itself. Through Jack, the story highlights the stakes of adult decisions and the importance of stability, affection, and honesty. 

He becomes a grounding force for both Eve and Jamie, reminding them that love extends beyond romance into responsibility and trust.

Leo

Leo is Eve’s former fiancé, a man who cared deeply but lacked the emotional capacity to support her in the ways she needed. While he wants to help, his method often involves problem-solving and analysis rather than empathy, making Eve feel examined rather than held. 

His reliance on structure and his own therapy sometimes turns into pressure on Eve to heal on a schedule that suits him. Their relationship suffers because neither can articulate their fears without triggering the other’s defenses. When Eve leaves, Leo’s reaction is driven by hurt and confusion, escalating into anger during their later conversation. He represents a version of life that is orderly, predictable, and emotionally distant, a life Eve can no longer inhabit. 

Though flawed, Leo is not malicious; he is simply a man who cannot bridge the emotional gap between them.

Maya

Maya is Eve’s anchor in New York, offering loyalty without judgment. Unlike others in Eve’s life, Maya listens without trying to fix her. She respects boundaries, offers practical help, and understands that Eve’s grief cannot be solved through reason alone. 

Maya’s presence reflects the importance of chosen family: people who stay steady when others cling to expectations or obligations. Her blend of humor, honesty, and gentle confrontation gives Eve space to unravel safely. While she worries about Eve’s Tennessee retreat, she ultimately trusts her friend to navigate her own pain. 

Maya embodies stability and unconditional support, and her confidence in Eve’s talent and resilience becomes one of the few lifelines Eve relies on.

Joan

Joan is a complex figure defined by control, fear, and good intentions warped by rigid beliefs. As Eve’s mother, she is deeply invested in appearances and propriety, convinced that strict guidance protects her daughter from harm. 

Her decision to force teenage Eve to surrender her baby comes from a blend of societal pressure, religious anxiety, and her own unresolved fears. Joan’s inability to acknowledge Eve’s pain creates a decades-long rift marked by silence and misunderstanding. 

Yet when Eve finally confronts her, Joan softens, revealing regret and a desire to reconnect. Her arc shows a woman who made damaging choices but is capable of growth once she allows herself to see her daughter’s suffering.

Roger

Roger is warm, approachable, and eager to maintain household harmony. He often acts as a buffer between Joan’s intensity and Eve’s sensitivity. 

However, his affable nature masks avoidance; he prefers comfort over confrontation, especially regarding the past. He genuinely loves Eve but struggles to face the harm caused by decisions made when she was seventeen. 

His quick retreat during the emotional conversation reflects his long-standing inability to engage with conflict. Roger represents a gentler form of parental failure: not cruelty, but passivity. Even so, his affection provides Eve with small, needed reminders of safety.

Lucy

Lucy is Jamie’s ex and a woman whose life has been shaped by instability and impulsive decisions. Though their romantic relationship deteriorated due to betrayal, Lucy is not portrayed as a villain. 

She is inconsistent, sometimes overwhelmed, and often caught between regret and new beginnings. Her engagement to Tyler and later pregnancy force Jamie to confront the parts of their past he hasn’t fully processed. Lucy’s presence highlights the complexity of shared parenting after heartbreak and the difficulty of rebuilding trust. 

Despite her flaws, she loves Jack and is trying to construct a stable life, even if she falters along the way.

Casey and Jelani

Casey, Jamie’s brother, and Jelani, Casey’s husband, form a supportive, vibrant duo who act as emotional scaffolding for Jamie. They bring levity, honesty, and a broad perspective, challenging Jamie’s assumptions and encouraging him to see his own value. 

They welcome Eve with warmth, reading her character quickly and recognizing how she helps Jamie open up. Their stable partnership contrasts with the chaos surrounding other relationships in the story, demonstrating what love looks like when built on trust and communication. Through them, Jamie gains reassurance, and Eve finds a place within a family structure that feels accepting and generous.

Hazel

Hazel, though deceased, is a quiet but powerful presence throughout the novel. Her cabin becomes a space where buried memories come to the surface and where Eve begins the long process of reclaiming her narrative. Hazel’s kindness toward both Eve and Jamie lingers in the way they remember her, shaping the environment that ultimately brings them together. 

The cabin, her legacy, stands as both a site of Eve’s deepest wounds and the place where she finally begins to heal. Hazel’s influence echoes through her actions in life and the refuge she leaves behind.

Themes

Themes

Grief and the Private Cost of Loss

Grief in Once Upon a Time in Dollywood is not treated as a single emotional state but as a full reshaping of identity. Eve’s sorrow comes from multiple directions at once: her miscarriages, the breakup with Leo, the unresolved trauma of her teenage pregnancy, and the exhaustion of constantly being expected to “recover” according to others’ timelines. 

Her pain is not clean or orderly. It shows itself through panic attacks, avoidance, emotional withdrawal, and an overwhelming sense that she has failed at both womanhood and adulthood. The book examines how grief becomes isolating when people around the sufferer insist on productivity, rationality, or emotional neatness. Eve’s parents want her to package her experience as a writing retreat, Leo wants her to accept his version of partnership, and her agent wants her to perform professional excitement. Every expectation piles on top of the core wound she has not yet spoken aloud: she lost a child at seventeen and was forced to surrender that grief before she even had the language to express it. 

Tennessee becomes the first place where she has space to experience loss without interruption. Jamie’s presence offers steadiness, not solutions, which allows her to finally acknowledge the cumulative weight of her experiences. The theme shows how healing often requires honest confrontation rather than silence, and how grief continues to shape choices long after the world expects a person to be “fine.”

Autonomy, Control, and Reclaiming Personal Narrative

The struggle for autonomy fuels Eve’s journey. Her parents removed her agency when they dictated the terms of her teenage pregnancy, sending her away and making decisions that shaped the next decade of her life. In adulthood, Leo continues this pattern in subtler ways—managing her feelings, pushing therapy formats that suit him, and assuming she cannot withstand solitude or conflict. Even well-meaning characters try to shape her path, offering their versions of what stability should look like. 

By leaving New York abruptly, Eve asserts the first significant act of self-direction in years. Yet autonomy is not simply the ability to leave; it is the ability to understand why departure was necessary. Through writing her play, examining old wounds, and confronting her parents, Eve begins to claim her narrative rather than inhabiting the version others wrote for her. 

Her relationship with Jamie complicates this process because she is drawn to him, but fears becoming a secondary figure in someone else’s life again—especially a life centered around a child. Autonomy becomes less about running and more about choosing honestly. When she finally tells Jamie the truth about her losses, she asserts control through vulnerability rather than avoidance. 

The theme reveals how personal freedom requires both boundary-setting and the courage to tell one’s own story without apology.

Parenthood, Caregiving, and the Weight of Expectations

Parenthood appears in the novel not as a single role but as a collection of pressures that influence every character differently. Eve sees motherhood as something she has been denied, first by force and later by fate. Her miscarriages intensify a belief that her body and her choices are unreliable. 

Jamie experiences fatherhood as both grounding and limiting; he loves Jack deeply yet feels his identity has been swallowed by responsibility. Lucy views motherhood through instability and longing, trying to reclaim her place in her son’s life after losing custody. These differing experiences intersect when Eve and Jamie connect. 

Jamie’s steady, practiced caregiving initially comforts Eve, but it also terrifies her because it reminds her of the child she never held and the years stolen by her parents. Meeting Jack becomes a symbolic threshold: it forces her to recognize that caregiving is not only about biology but about presence, patience, and humility. 

The book uses parenthood to explore how adults carry expectations shaped by culture, religion, and family narratives. Eve’s fear of being included in a family dynamic stems from the belief that she is broken or unworthy. Jamie’s fear of trusting a partner again reflects the consequences of betrayal. Through these fears, the novel questions who is permitted to feel unsteady while parenting and who is judged for it. 

Caregiving becomes a shared responsibility rather than a gendered expectation, challenging traditional ideas of what a “good parent” or “good partner” should look like.

Shame, Silence, and the Long Afterlife of Trauma

Shame shapes Eve’s emotional landscape more than she realizes. Her panic attacks and avoidance are rooted in years of being told not to discuss her teenage pregnancy, not to question her parents’ decisions, and not to complicate her relationship with Leo by expressing anger. Silence becomes the default mode for managing discomfort. 

This pattern keeps Eve locked in old wounds, unable to believe she deserves tenderness without proving her worth through emotional obedience. When she reaches the cabin, physical distance allows emotional truth to surface. Memories return not as sudden revelations but as steady pressure building toward confrontation. 

Jamie’s honesty about his own past—his mother’s affair, Lucy’s betrayal, and the loneliness that followed—creates a space where Eve begins to speak openly rather than filtering every thought for acceptability. The most significant moment in this theme occurs when Eve confronts her mother and finally names the harm done to her. Instead of restoring harmony immediately, the confrontation highlights how silence protected the adults at the expense of the child. 

The theme demonstrates that trauma does not disappear simply because time has passed; it lingers in behavior, relationships, and self-worth. Healing comes from refusing to remain silent, even when the truth disrupts family comfort.

Love as Choice Rather Than Rescue

Romance in Once Upon a Time in Dollywood does not follow the pattern of one character saving another. Instead, love becomes a series of choices that demand honesty, responsibility, and flexibility. Eve and Jamie are drawn to each other because each recognizes in the other a familiar loneliness. 

But attraction alone cannot overcome their fears: Eve fears being consumed, Jamie fears repeating past betrayals. 

Their separation after the argument in Tennessee shows that desire does not erase structural realities such as distance, custody, and career. When they reunite, the relationship deepens because they choose to reveal the parts of themselves that feel least safe—Eve’s losses, Jamie’s insecurities, and the tangled histories they carried alone. Jamie deciding to move to New York is not portrayed as a grand sacrifice but as a thoughtful decision rooted in what he wants for himself and Jack. Eve choosing to let him back into her life is not presented as romantic surrender but as grounded acceptance of partnership. 

The theme argues that love is strongest when built on mutual clarity rather than fantasy. It grows when both people understand each other’s pain, respect boundaries, and move toward each other not out of desperation but intention.