If You Give a Grump a Holiday Wishlist Summary, Characters and Themes

If You Give a Grump a Holiday Wishlist by Ann Einerson is a romantic comedy set against the snowy backdrop of a small-town holiday.

The story follows Presley Stafford, a spirited assistant with a love for holiday traditions, and Jack Sinclair, her stern, workaholic boss with a reputation for being a “grump.” When Jack’s professional demands threaten Presley’s long-awaited holiday with her family, the pair are forced into an unconventional arrangement that blends business with family festivities. As their worlds collide in the midst of laughter, chaos, and heartfelt moments, they discover that sometimes the greatest gifts come when you least expect them.

Summary

The story opens with a glimpse into the past. Jack Sinclair, the powerful and notoriously grumpy CEO of Sinclair Group, finds himself unexpectedly drawn to Presley Stafford during her unconventional interview.

Presley lacks the polished credentials Jack typically requires, but her confidence and determination win him over. This sets the stage for a complicated working relationship.

Fast forward to the present, Presley’s dreams of spending a cozy holiday in her hometown, Aspen Grove, Maine, are dashed when Jack demands her presence at work just before Christmas.

In a fit of frustration—and perhaps a touch of desperation—Presley negotiates a deal. She’ll work remotely from her family home, but only if Jack helps her complete her holiday wishlist, a cherished tradition.

Jack, ever the control freak, surprises everyone (including himself) by agreeing. The two board his private jet for Maine.

Presley’s family is warm and enthusiastic, quickly pulling Jack into their orbit. Caught off guard, Jack blurts out that he’s Presley’s boyfriend, hoping to deflect awkward questions about their working relationship.

Presley is mortified by his impulsive fib, and their awkward dynamic is only heightened when they’re forced to share her childhood bedroom. Despite the snark and bickering, a new, vulnerable side of Jack begins to surface.

As they tackle Presley’s wishlist—ice skating, decorating the house, caroling, and more—Jack’s lack of holiday spirit becomes apparent, often leading to comedic disasters. Presley’s patience and cheerfulness chip away at his icy exterior, and Jack’s efforts to participate, no matter how clumsy, endear him both to her and her close-knit family.

Presley’s protective brothers, especially Dylan, watch Jack closely, determined to ensure he doesn’t break her heart.

With each shared activity, the walls between Presley and Jack begin to crumble. Jack finds himself genuinely enjoying family games, local traditions, and the simple joys of small-town life.

Pranks from Presley’s brothers—ranging from harmless jokes to landing Jack briefly in a holding cell—test his resolve. These moments also force him to openly defend and clarify his feelings for Presley.

As they stumble through holiday mishaps, Presley and Jack’s chemistry deepens. The line between their professional roles blurs as they share increasingly honest conversations and moments of unexpected tenderness.

Presley, used to handling everything herself, struggles to trust Jack’s intentions. Jack, for his part, grapples with emotions he’s never allowed himself to acknowledge.

The holiday magic weaves its way through their days. There is a late-night snowstorm, a quest for the perfect Christmas tree, a horse-drawn sleigh ride, and heartfelt exchanges by the fire.

Jack, in a moment of vulnerability, begins to admit the feelings he’s been hiding behind sarcasm and stubbornness. Presley’s doubts linger, especially as she wonders what will happen when they return to their regular lives and demanding jobs.

Family, forgiveness, and self-discovery are at the heart of their journey. Presley’s family’s acceptance of Jack—even after learning the truth about their “fake” relationship—helps him see the possibility of a future beyond business deals and boardrooms.

For Presley, the holiday becomes not just about traditions, but about opening her heart to love, risk, and new beginnings.

By the end of their holiday together, both Presley and Jack are forever changed by the chaos, joy, and unexpected warmth they found—not just in each other, but in the magic of letting go and embracing the unknown.

Characters

Jack Sinclair

Jack Sinclair stands at the center of the story as the CEO of the Sinclair Group. He is initially depicted as a stern, disciplined, and sometimes emotionally distant boss.

Jack’s wealth and power seem to serve as a shield against personal vulnerability. His initial interaction with Presley reveals his tendency to keep people at arm’s length.

Beneath the gruff exterior, Jack is a man deeply uncomfortable with chaos and sentimentality. This makes him particularly susceptible to the unexpected warmth and messiness of Presley’s world.

As the novel unfolds, Jack’s carefully managed emotional defenses begin to crumble. Presley’s close-knit family and her infectious holiday spirit draw him out.

His journey is marked by gradual self-discovery and moments of embarrassment and humility, such as when Presley’s brothers prank him. Jack’s willingness to join Presley’s holiday wishlist, even when out of his element, signals his growing affection.

By the story’s end, Jack’s arc is one of opening up. He learns to express love and finds comfort in emotional vulnerability and family connection.

Presley Stafford

Presley Stafford is introduced as an ambitious, quick-witted, and resourceful woman. She refuses to let her lack of a traditional background hold her back.

Presley is hired by Jack for her moxie and competence. She consistently challenges him, both professionally and personally.

Her deep love for holiday traditions, small-town roots, and close relationship with her family are central to her identity. These traits directly contrast with Jack’s isolated, work-obsessed existence.

Presley is fiercely independent and deeply loyal. She never hesitates to stand up for herself when Jack oversteps.

At the same time, Presley possesses a playful, nurturing side that draws Jack out of his shell. Her emotional journey involves moving past skepticism and fear of heartbreak.

She learns to trust her own feelings and allows herself to believe in the possibility of a lasting romance. Presley’s interactions with Jack push her to examine the boundaries between her professional and personal life.

Her vulnerability in the later chapters highlights her complexity as both a romantic partner and a confident individual.

Dylan and Mrs. Stafford

Presley’s family, especially her brothers and her mother, play an essential role in grounding her. They also shape the story’s emotional landscape.

Dylan, the most vocal and protective brother, serves as a foil to Jack. He is openly skeptical of Jack’s intentions and unafraid to confront him.

Dylan’s protectiveness is a source of tension and a catalyst for Jack’s self-reflection. Jack is pushed to prove his sincerity and deepen his commitment to Presley.

Mrs. Stafford, Presley’s mother, embodies warmth, acceptance, and gentle wisdom. Her knowing approach adds a subtle layer of emotional support.

Mrs. Stafford quietly observes the budding relationship and recognizes the pretense before anyone else. She provides acceptance and reassurance.

The family as a whole represents everything Jack lacks but comes to cherish. They offer a sense of belonging, tradition, and unconditional acceptance.

Their playful dynamics, including pranks and teasing, bring levity to the narrative. They also expose the vulnerabilities of both Presley and Jack.

Themes

Professional Identity and Personal Vulnerability Within Power Imbalances

One of the most compelling and challenging themes in If You Give a Grump a Holiday Wishlist is the struggle faced by characters as they navigate the blurred lines between professional identity and personal vulnerability, especially in the context of significant power imbalances. 

Jack Sinclair, as a wealthy CEO, embodies the persona of untouchable authority, driven by expectations of control and efficiency.

Presley, his assistant, enters the relationship at a disadvantage, lacking both the formal credentials and the social status typically valued in his world. 

The forced proximity during the holidays intensifies their interactions, compelling both characters to confront how much of themselves is shaped by their public roles versus their private longings.

As the relationship evolves, the risk for Presley is not just heartbreak but professional fallout, while for Jack, it is the threat of losing the self-mastery on which his identity relies. 

The book interrogates whether true intimacy is possible when one person holds most of the cards, ultimately suggesting that vulnerability—though frightening—can be a transformative equalizer in relationships fraught with inequality.

Redemptive Power of Family Rituals and Small-Town Traditions in Healing Emotional Isolation

A nuanced theme running through the narrative is how the grounding force of family rituals and small-town traditions acts as a salve for emotional wounds and chronic isolation. 

Jack, accustomed to the sterile luxury of urban corporate life, finds himself utterly adrift amidst Presley’s boisterous, tradition-rich family in Aspen Grove.

The holiday wishlist, which might seem trivial, becomes a deeply symbolic tool—a roadmap to belonging and reconnection. Each activity Presley shares with Jack is an opportunity for him to confront the hollow routines of his life and rediscover joy, spontaneity, and the emotional nourishment found in genuine human connection.

The novel treats these rituals not as mere festive diversions, but as essential acts that mend old hurts, rebuild trust, and foster the kind of emotional intimacy that neither wealth nor status can buy. 

Through ice skating, pranks, and sleigh rides, the holiday customs expose hidden fractures, demand apologies, and inspire forgiveness, proving that such seemingly simple moments hold the power to redeem and transform even the most hardened hearts.

Negotiating Authenticity in the Face of Social Performance and Constructed Narratives

Another sophisticated theme explored is the struggle to maintain authenticity while being compelled to perform roles dictated by social and familial expectations. 

The entire premise of Jack posing as Presley’s boyfriend is an elaborate charade born out of convenience and professional necessity, but it quickly spirals into a high-stakes negotiation of truth and facade.

The novel deftly explores how every character, not just Jack and Presley, performs a version of themselves for family, community, and even for personal safety. 

Presley’s family—quick to test Jack’s intentions, yet keenly aware of the performative aspects of holiday reunions—are not mere foils, but participants in a collective storytelling where the truth often lurks beneath polite fictions and traditions.

The tension between what is real and what is merely performed generates conflict but also deep moments of self-recognition, as characters must decide whether to persist in the safety of constructed narratives or risk exposing their most vulnerable selves to potential rejection. The book suggests that authenticity, while difficult and sometimes painful, is ultimately the only sustainable path to lasting love and belonging.

Reconciling the Legacy of Emotional Detachment with the Desire for Intimacy and Acceptance

At its emotional core, the novel is a meditation on the legacy of emotional detachment—how habits formed in response to loss, disappointment, or professional demands create barriers to true intimacy. 

Jack, shaped by years of prioritizing business over pleasure, approaches relationships as transactions to be managed, not as sources of mutual nourishment.

Presley, too, has armored herself against disappointment, using her sharp wit and competence as shields against vulnerability. 

Throughout the narrative, both characters are forced to confront the emptiness of a life spent keeping others at arm’s length.

Through moments of conflict, confession, and reconciliation, the story investigates how characters learn to recognize and dismantle their emotional defenses. 

The slow shift from calculated detachment to tentative openness is not portrayed as a magical transformation, but as a messy, nonlinear process involving setbacks, awkward admissions, and, ultimately, the acceptance that to be fully loved, one must risk being fully seen.

The novel’s epilogue, with its focus on continued nurturing and the maintenance of romantic spark, underscores the idea that intimacy is not a destination but a practice—a daily choice to show up, to apologize, and to love without guarantees.