The Professional Proposal Planner Who Orchestrates Love in New York City

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If you want to see a marriage proposal this Valentine's Day, consider a visit to the foot of Central Park's iconic Bow Bridge. Time it right, and you may just witness a man get down on one knee — not just a half-kneel, either, but a full bend — take his girlfriend's hand, and ask her to marry him.

Scan the tableau, and you'll find a tall brunette lurking inconspicuously in the background, snapping photographs of the couple. That would be Ash Fox. In addition to photographing the proposal, Fox, 28, will have coached the groom-to-be on the right way to pop the big question and orchestrated the scene to maximize romance and minimize any awkwardness that comes from staging an intimate moment in a public space.

It will be a busy day for Fox. February 14th always is.

The Central Park scene is just one of three proposals scheduled for Valentine's Day proper. Meanwhile, on the days sandwiching the holiday, Fox has proposals lined up at, among other locations, Rockefeller Center, a hotel lounge, a midtown rooftop bar, and Central Park (again). Altogether, she will have crafted ten proposals over the course of this Valentine's Day weekend.

After all, Valentine's Day is a celebration of love, and Fox is in the business of romance. Proposals are her full-time job. While Valentine's Day is consistently nuts, her busiest period by far is the lead up to Christmas. "Most people get engaged before the New Year. It's insane — I don't have a life," she said. "I don't celebrate holidays." Last December, she organized 40 engagements.

To date, she estimates she's planned close to 1,000 proposals, all in the New York City area. (Shockingly, while a few proposals have been cancelled altogether, Fox says none of her clients have received a no.) Name an iconic or semi-romantic spot in the five boroughs, and Fox has orchestrated an engagement there. She's photographed dozens of couples in Times Square — on four separate occasions, she was also charged with renting out a billboard to help ask the big question — dozens more on rooftop bars and waterfronts across the city, one on a private yacht, and another in a castle in Tarrytown. A personal favorite was a proposal in the Nomad hotel bar The Library.

"That one was super cute," she said. Because the fiancée-to-be's favorite book was Jane Eyre, Fox helped her client incorporate the 19th-century novel into his proposal: They bought a copy, carved a heart shape in its center, and placed the ring inside. Fox strategically positioned it on a bookshelf at eye level by the bar. When the girlfriend arrived, she made a beeline for the book. As she opened it and glimpsed the ring, her boyfriend dropped to one knee.

"He knew her so well. He knew she was going to pick up that book!" Fox said. "That's the nice thing about a proposal where you're making it about the girl, not about yourself."

Fox didn't grow up pining to be a proposal planner — as with most meet-cute stories, it was more serendipitous than that. Originally from Bridgewater, New Jersey, Fox moved to the city to major in art at New York University. After she graduated in 2009, she got a job as a party photographer, chiefly for nightclubs and rock n' roll bands.

Naturally bubbly, she made friends with the men and women who consistently showed up at the same events, week after week. "One of my favorite things was seeing them fall in love and taking pictures of people who over time really got to know each other," Fox said. "I always loved photographing couples."

Wanting a more normal schedule, in 2011 she stopped shooting parties and began photographing weddings and family events. At one such gathering, she met Julie Sahni, a prominent Indian chef who wanted professional photographs of her son proposing to his girlfriend. Fox was hired to shoot the engagement, but she also helped plan the surprise proposal: An elaborate Central Park affair that involved family members throwing rose petals from Bow Bridge as the couple embraced below.

"It was a turning point," said Fox.

Previously, she'd viewed proposal photography as an intrusion of what should be a private, organic moment. But being part of that first proposal — witnessing how meaningful it was not just for the bride and groom, but their families as well — changed her mind. She was hooked.In the five years since, Fox's role has evolved from a proposal photographer to a full-service planner. Her services range from $550 for relatively bare-bones proposals, typically conducted in public spaces, to upwards of $1,500, for a more elaborate proposal in private venues with personalized setups. "If they want a rooftop with a musician and rose petals...I can do all of it."

Logistics aside, Fox finds what her clients — the vast majority of whom are young men in their 20s and 30s — need most is emotional support and guidance. Her role is a cross between a therapist and a strict coach. By this point, she knows what works and what doesn't. All clients receive a complimentary planning session to help them avoid the most common proposal pitfalls: a lack of directness and the failure to decisively take a knee once they've reached the chosen location.

In her early days, back when she was still primarily a photographer, "I noticed most guys' natural impulse was to take the girl to a spot, stand around — the seasons are changing while they're standing there — until the girl is like, 'Why are you acting weird?'" While most manage to eventually blurt out the question, it wasn't a very romantic approach.

To avoid this awkward pre-proposal shuffle, Fox walks through the ritual with her clients in person. "I show them how long to stay on their knee," she said. "I show them how long to hold her hand." Her constant mantra: it's not about the ring, it's not about the setup — ultimately, "it's just about her and you. This is a once-in-a-lifetime moment, so take your time."

Part of her job often includes convincing guys to tone down the theatrics. Whenever possible, she advises not to include friends and family. "They'll be there at the wedding. Make the proposal an amazing memory just between the two of you, so you can tell everyone together." And despite the surge in popularity, she is vehemently against staging viral proposal videos. "It's not about you," she said, clearly exasperated.

Her distaste for the genre is perhaps best summed up by a recent proposal clip, in which the guy asked his girlfriend to marry him via a homemade video that he publicly screened at their local theater before the trailers started. "The second the girl sees the guy on screen, she knows, ‘Oh, he's proposing to me,'" Fox said. "So by the time he went down on his knee, the whole expression on her face was lost." More upsetting, "The whole movie was about him.

Fox routinely steers clients away from the gimmicky and towards meaningful simplicity."I'm not into you dancing a jig before the proposal...showing off for friends or showing off for Facebook. To me, that's so not romantic," she said. "Instead, take her to a beautiful, serene area and propose to her. Focus on your words."

"This is a once-in-a-lifetime moment, so take your time."

While Fox always tries to put herself in the woman's shoes when proposal planning, despite the vicarious anticipation and witnessing hundreds of variations of the question "Will you spend the rest of your life with me?" Fox said she has no idea how she'd like her own proposal to play out. "Maybe it's because I've planned so many."

It doesn't help that the job makes dating hard. Typically, she saves the intricacies of her profession for the third or fourth date. "When guys hear what I do, they get nervous," she laughed. She's currently dating someone casually, "But honestly? I don't know if I'll ever get married."

For now, she's focused on building beautiful proposals for other people. That means she will not celebrate Valentine's Day with her new-ish boyfriend over a candlelit dinner. Instead, she will criss-cross the city, providing emotional support to a crew of jittery men as they prepare to ask one of the most important questions of their lives.