Holly’s Holiday 2012

Holly Maddox [Claire Coffee] Claire Coffee works in advertising at Quin+Gunn in New York City, where she has her own office and a bumbling but sweet secretary Meg Annie Quinn. Two weeks before Christmas, Holly feels a bit disappointed that it isn’t snowing, even as Meg keeps a lighthearted eye on Holly’s offbeat office life—like the impulse to order pizza at 2 a.m. on a Sunday. Holly is someone who tends to wear a smile, though, and her friend and co-worker Deena Gabrielle Dennis has Marcos Aketza López Totorika and is pushing Holly to find a man of her own.

Holly’s boss Livingston sets a new assignment: a campaign for Chelsea Diamonds, requiring Holly and photographer Milo Ames Jeff Ward to brainstorm ideas near the holiday season. The two clash in the conference room about how the campaign should feel—Holly wants to prove that Christmas magic means happiness through image and aspiration, featuring the most polished, successful people; Milo believes the heart of the message should come from real, relatable people. The debate is pointed but ultimately professional, and it begins to reveal ad philosophies that will pull Holly in two different directions.

Meanwhile, Darryl, the tech guy, has a crush on Meg, adding a touch of small-town charm to the high-energy office vibe. To shake things up, Holly slips into a flashy dress Deena provided and heads to a noisy dance club, where she runs into Deena and Marcos. Marcos catches the eye of other pretty women, but Deena is confident that Marcos will always come back to her. Holly, however, doesn’t lock eyes with anyone that night, though Milo is there and ends up taking a picture of Holly holding hands with him, a moment that will later feel like a tease of fate.

The next morning, a call from Milo about work pulls Holly back toward reality. On her walk to the office, Holly falls and hits her head, and when she wakes, she meets the perfect man—tall, charming, and seemingly tailor-made for her. Bo Ryan McPartlin helps her up and suggests dinner. Holly arrives at the restaurant with a flutter of excitement, but Bo is already mingling with others, and he reveals that he used to work in advertising and has a track record in campaigns. He shares a bittersweet truth about past relationships and explains that his parents—who are a bright, almost too-perky contrast to Holly’s sensibilities—are coming to join them for a look at “the perfect life.”

Back at the office, Holly and Deena behave like teenagers again, their laughter echoing through the halls with a dolphin-like soundtrack that punctuates their chemistry. Milo, meanwhile, continues to push for a breakthrough on the Chelsea Diamonds project, reminiscing about his earlier journalism days and his affinity for small-town life, a thread that hints at his longing for authenticity and belonging.

When the scheduled photo shoot finally arrives, the crew finds out it has been canceled. The only deposit that matters is Bo’s word, but the truth is more complicated: Bo is behind the cancellation, and Dex—an ambitious, well-known photographer—begins staging “perfect” shots with models who don’t radiate happiness. Holly and Meg are asked to participate, but the atmosphere remains uneasy, as Bo’s ex Brandi appears, injecting tension into the set. The shoot collapses, leaving Milo to salvage whatever he can from the wreckage and push forward with a more grounded approach.

Back at the office party, Meg Annie Quinn brings music to life, while Marcos arrives with Brandi, looking dazzling in the wrong setting, and Deena confronts Marcos about his priorities. Deena, in turn, shares the true story with Livingston, revealing that Holly wasn’t at fault and that the supposed “perfect” shoot was more fragile than it appeared. Deena also introduces Kyle, a new connection from upstairs who might be a better match for Deena than Marcos ever was.

Milo remains hopeful that Holly will realize he’s the right person for her, but Holly’s feelings aren’t clear yet. As the party unfolds, she chases a realization that breaks her heart—the glamorous fantasy Bo represents isn’t what she wants. A misstep sends Holly crashing to the ground again as she pursues what could be, and Milo is there beside her, a quiet anchor in the chaos.

Holly wakes in the hospital with Milo by her side, confessing that he claimed to be her husband to stay with her. The reality is gentler but harder to face: Holly has lived through a fantasy that never truly existed, and she learns that nothing has happened the way she imagined. The doctor advises rest, but Holly’s determination to finish the Chelsea Diamonds campaign remains unwavering. She presses for her laptop and the tools she needs to work, insisting that her project deserves honesty, even if it has to be reworked from scratch.

Kyle, not from Australia, appears as a perfect match for Deena, complicating the office dynamics in subtle, hopeful ways. As Holly surveys the evidence of what unfolded in her “perfect world,” she realizes that the campaign should celebrate ordinary people, not idealized glamour. The only image with real meaning beyond the fantasy is the hands of Holly and Milo dancing at the club—the moment that feels most authentic.

In the final act, the Chelsea Diamonds campaign is reimagined around genuine connection rather than glossy perfection. The film closes on that shot, a single, honest image projected on a bus with the Chelsea Diamonds logo and slogan, while the department store mannequin fades from the frame. The message lands with quiet resonance: authenticity can outshine illusion, and sometimes love arrives not as a flawless fantasy but as a shared, imperfect moment that endures.