Flopping in a Winter Wonderland Summary, Characters and Themes
Flopping in a Winter Wonderland by Jason June is a LGBTQ+ holiday romantic comedy set on a magical island where Christmas is celebrated all year round. At its core, the story is about two teen boys—Aaron and Kris—grappling with love, loss, identity, and emotional vulnerability.
While one avoids feelings altogether to protect his family, the other embraces charm and theatrics to fight for a queer-inclusive legacy. The novel cleverly mixes humor, romance, and activism with snowy hijinks and tender self-discovery. Through a festive backdrop, it explores the emotional growth of two very different young men learning what it means to open their hearts, especially when the stakes are personal.
Summary
Aaron Merry arrives in Winter Wonderland with his heart firmly closed off and his mind focused solely on supporting his heartbroken older brother, Casey, who recently broke up with his long-time girlfriend Raquel. Aaron, known in his family as the one who holds everything together, prides himself on logic and emotional restraint.
He’s dedicated to helping Casey recover over the holidays and has no intention of letting anything—or anyone—distract him from that mission. But Winter Wonderland has a way of catching people off-guard, especially when it’s filled with flamboyant locals, over-the-top traditions, and a game called The Race, which turns romance into a strategic holiday sport.
Kris Bright, a senior on the island, is one of the Wonderers—locals who help tourists experience the magic of Christmas. Every year, the Fling Ring, a mischievous group of Wonderer seniors, participates in The Race: a contest where they compete to get a tourist to fall in love with them over the course of their vacation.
The winner gets a trip to New York with Anjelica Pérez-Kringle, the daughter of the island’s founder. But for Kris, the Race is more than just a holiday stunt.
His real goal is to secure an audience with the elusive Kringle and convince him to change the island’s traditions and allow queer representation—starting with reinstating Kris’s Uncle Toby, who was denied the role of Santa because he’s gay.
After a failed romantic attempt with another tourist, Kris meets Aaron through a slapstick accident at a flash mob event, where Aaron quite literally knocks Kris off his feet. What starts as a comedic moment full of awkward tension becomes the first step toward something deeper.
Aaron, unused to physical or emotional intimacy, is stunned by the rush of feelings he begins to experience. Kris, on the other hand, is intrigued by Aaron’s grumpy charm and logical mind.
When Kris shows up later with a gift basket for Casey, Aaron panics and slams the door in his face, unable to reconcile his feelings with his self-appointed role as his brother’s caretaker.
The story becomes even more tangled when Raquel shows up on the island with Liam, the most famous Wonderer, as her new boyfriend. Casey, hopeful and delusional, sees her presence as a sign that they are destined to reunite.
Concerned, Aaron decides he must prevent Casey from backsliding into heartbreak and recruits Kris for help. Their plan: orchestrate a romantic setup between Raquel and Liam to keep her distracted and away from Casey.
Kris and Aaron’s alliance forces them to spend more time together, navigating the island’s holiday spectacles while also confronting their own growing connection. Despite the scheme, their moments alone become filled with accidental closeness, nervous glances, and emotional confessions.
A midnight snowmobile ride ends with Aaron’s first kiss—a moment that shakes him to his core. Kris, too, is touched, recognizing in Aaron something far more meaningful than the scripted romance he’s used to performing in The Race.
Meanwhile, their sabotage plan goes awry. The romantic carriage ride Aaron and Kris set up for Raquel and Liam is hijacked by Casey, who mistakenly thinks it was meant for him and Raquel.
With the plan unraveling and their motivations growing more conflicted, Aaron and Kris chase after the couple through the snowy streets, their emotions in chaos. Kris begins to question the entire foundation of The Race, while Aaron starts to let go of his rigid emotional control.
Complicating the emotional chaos is Kris’s internal struggle with his reasons for participating in The Race. Though he plays it cool, his true purpose is tied to deep hurt: his Uncle Toby, a talented toymaker and a man Kris views as the rightful Santa, was rejected simply for being gay.
Kris believes that if he wins The Race, he can finally earn a conversation with Kringle and push for systemic change on the island. But with Aaron now in the picture, the boundaries between strategy and sincerity begin to blur.
When the Race comes to its dramatic conclusion, Kris and Aaron’s relationship is exposed, and it crumbles under the pressure. Hurt and heartbroken, Kris channels his feelings into a bold stand against Kringle, delivering a moving speech about love, inclusion, and the need for queer Santas.
His bravery and vulnerability move Kringle to change the rules, officially allowing queer representation in Winter Wonderland traditions. Uncle Toby is reinstated, and Kris becomes a quiet hero in his community.
Back in Newport Beach, Aaron begins to piece himself back together. He enters therapy with his dad and Casey, confronting the emotional walls he’s built since his mother abandoned the family.
With each session, Aaron slowly starts to understand that responsibility and vulnerability don’t have to be mutually exclusive. Watching Kringle’s press conference on TV, where Kris’s advocacy is praised, Aaron realizes the depth of what they had—and what he’s ready to fight for.
With some encouragement from Casey, Aaron reaches out to Kris and discovers that Kris has moved to Southern California to help launch Winter Wonderland Too, a holiday experience on the mainland. Their reunion is marked by openness and heartfelt confessions.
Kris shares that he still loves Aaron, and Aaron, now unburdened by his old fears, is finally able to say the same. Their relationship, once built on schemes and misdirection, now has the chance to thrive in honesty and love.
The novel ends with the two boys laughing, kissing, and planning a future where they support each other not because they have to, but because they choose to.
In the whimsical world of Winter Wonderland, Flopping in a Winter Wonderland delivers more than just holiday cheer—it gives readers a beautifully real and affirming love story.
Characters
Aaron Merry
Aaron Merry is a deeply introspective and emotionally guarded teen whose defining characteristic is his self-imposed role as the emotional anchor of his family. He views himself as the “robot”—logical, detached, and wholly responsible for keeping things together, especially after his brother Casey’s long-term relationship falls apart.
His internal world is marked by tension between duty and desire, and this dichotomy drives his narrative arc in Flopping in a Winter Wonderland. Aaron is fiercely loyal and believes that any personal indulgence, particularly in the realm of romance, would betray the commitment he made to support Casey through heartbreak.
This sense of self-sacrifice stems from earlier familial trauma—his mother’s abandonment—and manifests in a strict emotional code he struggles to break.
Aaron’s encounter with Kris unearths feelings he has long repressed. Their first meeting, infused with both slapstick comedy and instant chemistry, forces Aaron to confront desires he has carefully tucked away.
The romantic feelings that begin to stir within him are both exhilarating and terrifying. He is not accustomed to vulnerability, and his deeply analytical mind resists the pull of emotion at every turn.
Yet, Kris’s consistent presence and emotional generosity gradually chip away at Aaron’s walls. The evolution of their relationship becomes a mirror for Aaron’s internal journey—away from hyper-responsibility and toward openness.
The turning point for Aaron comes when he is forced to confront the emotional consequences of his stoicism. His breakdown in front of his father is not just a personal unraveling but a declaration of his need to be more than a caretaker—it is an admission of his humanity.
Aaron’s journey is about learning to let go, to accept love without guilt, and to embrace the chaos of feeling. By the end of the story, his growth is not only seen in his romantic vulnerability with Kris but also in his renewed efforts to reconnect with his family and heal old wounds.
Kris Bright
Kris Bright is a charismatic, witty, and emotionally perceptive native of Winter Wonderland whose extroverted personality often masks a deeper well of frustration and longing. While he initially appears to be simply a flamboyant and strategic competitor in “The Race”—a local tradition where residents try to win the affections of tourists—his motivations are far more profound.
Kris’s true aim is not personal glory but justice for his Uncle Toby, who was denied the honor of playing Santa Claus due to his sexuality. This backstory reveals Kris’s deep-seated commitment to advocacy, identity, and equity within his conservative community.
Kris navigates life through performance: he is expressive, charming, and quick to create romantic illusions for the sake of the Race. But this very performativity becomes stifling when he meets Aaron, who is so different from the usual emotionally available, flirty tourists Kris is used to.
Their chemistry feels real—raw even—and Kris begins to see that authenticity can offer more than performance ever could. With Aaron, Kris is not just a Wonderer or a competitor—he becomes someone who is seen, someone whose dreams and vulnerabilities are valued.
As the story progresses, Kris’s emotional depth becomes more visible. He grapples with guilt over his uncle’s past, fear of rejection, and the intense pressure to both win the Race and stay true to himself.
When his romance with Aaron becomes public and the deception behind the Race is exposed, Kris faces public scrutiny and personal heartbreak. But it is in this crucible of crisis that Kris finds his voice, delivering a moving appeal to Kringle that challenges institutional norms and demands inclusion for queer individuals.
His victory is not just about winning the Race—it’s about reshaping the very foundation of Winter Wonderland to make space for people like him and Uncle Toby.
Kris’s character arc is both romantic and revolutionary. He starts as a boy playing a role and ends as a young man advocating for systemic change, finding love and authenticity in the process.
His reunion with Aaron in Southern California is the final confirmation that love, when honest and fought for, can transcend even the most artificial of boundaries.
Casey Merry
Casey, Aaron’s older brother, plays a secondary yet pivotal role in shaping the emotional stakes of Flopping in a Winter Wonderland. Reeling from a devastating breakup with his longtime girlfriend Raquel, Casey arrives in Winter Wonderland heartbroken and hopeful—clinging to the idea that the magic of the holidays might rekindle their lost romance.
His character oscillates between childlike optimism and heartbreaking delusion, as he misinterprets nearly every signal from Raquel as a sign of destiny. This misguided hope adds a layer of tension to Aaron’s journey, as Aaron feels responsible for protecting Casey from further emotional harm.
Despite his emotional volatility, Casey is not portrayed as weak or foolish. Instead, he is a symbol of romantic idealism, someone who believes deeply in love’s power to transcend mistakes and time.
His over-the-top efforts to reunite with Raquel—often comically misguided—are tinged with a sincere vulnerability that endears him to the reader. In contrast to Aaron’s calculated nature, Casey is emotionally impulsive, which makes their brotherly dynamic all the more poignant.
Casey becomes both the reason Aaron resists romance and, ironically, the catalyst that pushes Aaron to embrace it.
By the end of the novel, Casey’s role evolves from the emotionally needy brother to someone capable of recognizing his own patterns and healing alongside Aaron. His presence also facilitates the family’s broader emotional reconciliation, particularly in therapy sessions back in Newport Beach.
While not the primary focus of the narrative, Casey’s character adds emotional depth and serves as a foil that highlights both Aaron’s growth and the enduring importance of familial love.
Anjelica Pérez-Kringle
Anjelica Pérez-Kringle is a dynamic and rebellious figure within Winter Wonderland’s tightly controlled holiday narrative. As the daughter of the island’s founder, she possesses a unique position of power and visibility, but she is estranged from her family and uses her influence to uplift marginalized voices—particularly Kris’s.
Anjelica is unapologetically bold, mischievous, and emotionally astute. Her home, which doubles as a palace and a kind of emotional refuge, becomes a sanctuary where Kris can speak freely and feel supported.
Anjelica’s role, while limited in screen time, is crucial to the unfolding of Kris’s arc. She is one of the few characters who genuinely listens to Kris and encourages him to step beyond the limitations imposed by the Race.
She represents both resistance to tradition and hope for a more inclusive future. Her faith in Kris validates his mission, and her revelation that Aaron might be falling for him becomes the emotional spark that propels Kris to open his heart.
Beyond her function in Kris’s journey, Anjelica serves as a symbolic figure—a bridge between oppressive tradition and progressive reformation. Her character, with her sharp wit and warm generosity, embodies the transformative potential of allyship and familial defiance.
Uncle Toby
Uncle Toby is the quiet, emotionally powerful heart of Kris’s backstory. Though he appears sparingly in the narrative, his influence looms large.
Toby was denied the role of Santa Claus solely because of his sexuality, a rejection that led to his self-exile and emotional estrangement from the community. Kris’s mission in the Race is deeply tied to avenging this injustice and restoring his uncle’s dignity.
Toby’s existence in the margins of Winter Wonderland’s story is a commentary on systemic exclusion and the quiet pain of erasure.
Despite his past trauma, Toby is a source of wisdom and emotional clarity for Kris. When Kris faces his lowest moment, Toby counsels him not to withhold his feelings out of fear.
His presence is a calming, grounding force, and his final reappearance—through Kris’s successful appeal to Kringle—symbolizes both personal vindication and broader societal acceptance. Toby’s character is a poignant reminder of the personal stakes behind systemic change, and his eventual reinstatement into the Christmas canon is one of the novel’s most cathartic victories.
Themes
Emotional Vulnerability and Healing
Aaron’s journey is defined by his resistance to vulnerability and his eventual realization that emotional exposure is not a weakness, but a necessary step toward personal healing. Having taken on the emotional burden of his broken family—particularly after his mother’s abandonment—Aaron believes that stoicism and control are the only ways to protect himself and those he loves.
His approach to life is rooted in logic, responsibility, and self-sacrifice, leaving no room for unpredictability or affection. This coping mechanism, though effective in preventing pain, also prevents joy and connection.
When he meets Kris, whose warmth and charisma are immediately disarming, Aaron’s emotional shell begins to crack. Their accidental physical closeness during the flash mob ignites a discomfort he doesn’t understand at first, and his panicked, often hilarious attempts to ignore his feelings only highlight how deeply unprepared he is for romantic intimacy.
The kiss they eventually share doesn’t just signal attraction—it forces Aaron to confront the absence of closeness he’s long accepted as normal. His eventual emotional breakdown, especially in front of his father, marks a crucial turning point: Aaron no longer needs to maintain the illusion of perfection.
Through Kris and the relationships he rebuilds with his family, he begins to understand that love requires risk and that vulnerability is a gateway to healing, not harm.
Queer Identity and Inclusion
Kris’s arc centers on the tension between performative acceptance and genuine inclusion, especially within the context of Winter Wonderland’s rigid traditions. While the island outwardly celebrates joy and love, its refusal to embrace a queer Santa—exemplified by the exclusion of Kris’s uncle Toby—reveals a deeper conservatism masked by festive decor.
Kris, raised in a world where he’s expected to entertain and charm guests, learns how to wield charm and affection as tools, especially through his participation in the Race. Yet his confidence is a veneer, a way to claim power in a space that refuses to validate him fully.
His relationship with Aaron opens a new dimension of authenticity for him, one not rooted in performance or strategic gain. But the injustice against Toby remains unresolved in his heart, driving his need to win not just the competition, but a place at the table where decisions are made.
Kris’s passionate confrontation with Kringle is the narrative’s most overt political moment, transforming his personal longing into a broader fight for justice. His successful advocacy leads to institutional change: queer Santas become part of the Winter Wonderland mythos.
Kris’s triumph is not just romantic or emotional—it’s a reclaiming of history and an act of visibility that affirms the importance of being fully seen, not merely tolerated, within one’s community.
Family Obligations and Personal Freedom
Both Aaron and Kris are caught in the tension between loyalty to family and the pursuit of personal freedom. Aaron has devoted himself to caretaking, especially when it comes to his brother Casey, whose breakup drives the initial decision to travel to Winter Wonderland.
Aaron’s sense of duty to Casey is so strong that he suppresses his own desires, convinced that any pursuit of joy—particularly romance—would be a betrayal. This burden he places on himself reveals how deeply he equates love with responsibility and guilt.
Meanwhile, Kris’s obligation manifests differently: he wants to restore his uncle’s dignity and seeks to change the island’s discriminatory traditions, even if it means compromising his own chances at love. Each boy must navigate what it means to love family without sacrificing their own happiness.
Aaron learns that being there for Casey doesn’t require martyrdom, and Kris discovers that advocacy can coexist with personal truth. Their respective journeys highlight the importance of boundaries and the realization that true love—familial or romantic—should never demand self-erasure.
Love Beyond Performance
The dynamic between Kris and Aaron constantly questions the authenticity of romantic expression. For Kris, romance begins as a game—a performance honed over years as part of the Race.
His charm, wit, and attentiveness are real, but they’re often deployed strategically. The tension for him lies in distinguishing what is genuine from what is enacted for advantage.
Aaron, in contrast, avoids performance entirely. He is guarded to the point of emotional paralysis, suspicious of any expression that seems too easy or too polished.
Their romance evolves against the backdrop of this tension, with each boy slowly learning to unlearn their coping mechanisms. For Kris, love with Aaron is not a game to be won but an experience that challenges his belief that performance is his only value.
For Aaron, loving Kris requires letting go of control and surrendering to the messy, unpredictable reality of affection. When their relationship nearly implodes after the truth about the Race comes out, it is not the spectacle of the holiday competitions but their quiet, vulnerable moments—emotional breakdowns, heartfelt conversations, and the decision to reunite—that affirm the realness of their love.
The story insists that true connection arises not from grand gestures, but from honesty, humility, and shared emotional labor.
Transformation Through Conflict
Conflict acts as a catalyst for growth throughout Flopping in a Winter Wonderland, forcing characters to confront uncomfortable truths and revise long-held assumptions. Whether it’s the external conflict of sabotaging a romantic rival or the internal struggle between desire and duty, both Aaron and Kris are shaped by the friction around them.
Aaron’s conflict with Casey over Raquel’s return becomes a mirror for his own unresolved feelings about control and abandonment. His decision to manipulate the situation in order to protect Casey ironically mirrors the very behavior he despises in others—intervention without consent.
Kris, on the other hand, navigates the emotional conflict of being both a competitor in the Race and someone who genuinely falls for Aaron. These layers of contradiction—between strategy and sincerity, between pride and vulnerability—create a narrative where growth is never easy, but always honest.
Importantly, the resolution of these conflicts doesn’t erase the hurt; instead, it leads to a deeper understanding of the self and others. The transformation comes not from avoiding pain, but from sitting with it long enough to extract meaning, change course, and move forward with more clarity and compassion.
Reimagining Holiday Magic
The setting of Winter Wonderland is crucial—not just as a backdrop but as a thematic device that critiques and reimagines the cultural myths of Christmas. Traditionally, holiday stories emphasize magic, family, and happily-ever-afters, often excluding or marginalizing queer experiences.
In this narrative, the familiar elements—reindeer, snow, Santa Claus, matchmaking schemes—are all present but subverted to include diverse identities and emotional realities. The Race, while framed as a whimsical romantic contest, becomes a vehicle for exploring deeper issues of performativity, exploitation, and authenticity.
Kris’s goal to insert queer representation into the fabric of the island’s traditions forces a reevaluation of who gets to be part of the magic and who gets left out. Aaron’s emotional journey from cynical bystander to open-hearted partner also reflects a broader reframing of what holiday joy looks like: not in idealized perfection but in authentic, sometimes messy connection.
The culmination of the story—where queer Santas are publicly affirmed and a romance built on mutual respect blossoms—redefines Christmas not as a static tradition but as a living, inclusive experience. In doing so, Flopping in a Winter Wonderland transforms the holiday genre into something more expansive, more truthful, and ultimately, more magical.