Holiday Proposals in NYC: Magic, Mishaps, and Memorable Moments
In the heart of New York City during the holiday season, love stories unfold against a backdrop of twinkling lights and festive cheer. According to Proposal 007, a specialized company that has orchestrated over 2,000 marriage proposals since 2015, the Rockefeller Center ice rink reigns supreme as the most coveted spot to pop the question. However, this romantic setting comes with its own unique challenges. Co-founder Tatiana Caicedo reveals that the $1,500 package to rent the rink often leads to unexpectedly heartwarming moments as nervous suitors struggle to balance on ice skates while attempting to get down on one knee. “Most of the time, the guys are falling and the girls have to hold them,” Caicedo shares, recounting a recent proposal where the groom-to-be took a serious tumble before shakily getting into position. Despite the physical awkwardness, these moments often transform into “perfect Christmas proposals” straight from a Hallmark movie, with genuine surprise and emotion that can’t be scripted.
December marks the busiest season for Proposal 007, with 210 proposals planned this month alone, most concentrated around the Christmas weekend. The company, founded by Caicedo alongside photographer Vlad Leto, has witnessed countless memorable moments over the years, including what they call “the ring drop” – a surprisingly common disaster. One particularly dramatic incident occurred at Brooklyn Bridge Park, where a proposer accidentally dropped the engagement ring between the cracks of steps near Jane’s Carousel. The hiding family members immediately sprang into action, lying on their stomachs with sticks to retrieve the precious item. In another case, a panicked groom-to-be forgot the ring in an Uber and had to leave his blindfolded girlfriend with the proposal planners while he frantically tracked down the driver. These mishaps, while stressful in the moment, often become cherished stories in a couple’s journey.
Wardrobe malfunctions add another layer of unpredictability to these carefully orchestrated events. Caicedo laughs as she recalls a woman who unknowingly wore a shirt declaring “Just Say No” to her own proposal, creating an ironic scene as her boyfriend had arranged for an entire restaurant to serenade her while he proposed. Despite planning thousands of engagements, Caicedo has witnessed only one outright rejection in her decade of business – a particularly poignant moment where the hopeful proposer remained standing alone inside a heart-shaped arrangement of candles after his girlfriend walked away. More commonly, however, she notices couples who say “yes” in the moment but later separate before reaching the altar. “Because I follow everyone on Instagram, I see some couples are no longer together,” she admits, suggesting that the public nature and elaborate staging of these proposals sometimes create pressure that leads to acceptance despite underlying doubts.
The logistics of planning perfect proposals in New York City present their own challenges. Even with special event permits that reserve park spaces for an hour, public locations remain vulnerable to unexpected interruptions. Caicedo recalls a Fourth of July proposal where the climactic moment was photobombed by a passerby wearing a Nathan’s hot dog hat, immortalized forever in their engagement photos. The company’s most expensive offering – a $4,200 Times Square billboard proposal featuring the couple’s images and the words “Will You Marry Me?” for ten minutes – has occasionally fallen victim to New York’s notorious traffic, with some couples arriving too late to see their own proposal displayed on the massive screens above the crowded square.
These proposal mishaps, rather than detracting from the special moment, often enhance the authenticity of the experience. The nervous fumbling, unexpected falls on ice, and scrambles to retrieve dropped rings become part of the unique story that couples will tell for years to come. The unscripted moments – a fiancée steadying her wobbling partner as he attempts to propose on skates, or family members banding together to rescue a lost ring – demonstrate the support and teamwork that form the foundation of lasting relationships. Even when things don’t go exactly as planned, these imperfections often create more genuine, emotional memories than a flawlessly executed proposal could offer.
Despite the occasional mishaps, Proposal 007 continues to help hundreds of couples each year create magical moments in New York City’s most iconic locations. The company’s work captures a fascinating intersection of private emotion and public spectacle, personal milestones against famous backdrops. Whether it’s a secluded spot in Central Park or the dazzling center of Rockefeller Plaza, these carefully orchestrated proposals – mishaps and all – have become part of New York’s romantic landscape, especially during the holiday season. As Caicedo observes these life-changing moments, she witnesses not just the beginnings of engagements but the unfiltered, unscripted reactions that reveal the true nature of relationships. In a city known for its tough exterior, these vulnerable moments of love and commitment, complete with their stumbles and recoveries, offer a glimpse into the very human heart of New York.
