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Falling in love: These NYC marriage proposals flopped— literally

December 20, 2025
in News
Falling in love: These NYC marriage proposals flopped— literally

They really fell for their fiancées.

The most sought-after NYC spot to pop the question during the holidays is the ice rink at Rockefeller Center, according to Proposal 007, a company that helps men plan lavish engagements in the Big Apple.

However, most guys don’t consider how tricky it is to get down on one knee on a sheet of ice — a package that costs $1,500, which includes renting out the rink, photos and video.

“Everyone wants to propose on the ice rink, but not everyone knows how to skate. You need to get on one knee in the skates, so if you’re not a professional, it’s really hard to do. So most of the time, the guys are falling and the girls have to hold them,” the company’s co-founder Tatiana Caicedo told The Post.

A man has fallen on his back on an ice skating rink while a woman stands over him during proposal at Rockefeller Center
Many of the men who rent out the Rockefeller Center ice rink to propose actually don’t know how to skate. Vlad Leto
A man proposes to a woman on an ice rink at night, with a large illuminated Christmas tree and golden statue in the background.
December is the busiest time for the Proposal 007, a company that helps plan lavish engagements in the Big Apple. Vlad Leto

“One we had two days ago, he was skating to get to the spot to propose and he just fell really bad. Then he’s getting on one knee, and you can see he’s shaking, trying to keep his balance. And she’s holding him, saying, ‘You can do it.’”

December is the busiest time for the company, which planned 210 proposals this month, with most happening this weekend.

Caicedo, an event planner — who launched the company in 2015 with photographer Vlad Leto and has orchestrated more than 2,000 proposals — said another common disaster is “the ring drop.”

“It happens so many times,” she lamented.

Man dropping the ring in Brooklyn bridge park.
One common proposal mishap is “the ring drop,” Tatiana Caicedo, co-founder of Proposal 007, told The Post. Vlad Leto
A group of people looking for a dropped engagement ring in Brooklyn Bridge Park.
“The family ran out and I have pictures of them all laying on their bellies, trying to get it out,” Caicedo recalled. Vlad Leto

One of the worst occured in Dumbo’s Brooklyn Bridge Park — with a man asking for his girlfriend’s hand on the steps behind Jane’s Carousel.

“The man is proposing, their family is hiding, and then the ring fell in the crack of the steps. And the family ran out and I have pictures of them all laying on their bellies, trying to get it out,” she said.

“They got sticks and they did take it out.”

Some grooms-to-be misplace the sparkler before even getting to the venue.

“A guy forgot his ring in the Uber. The girl was blindfolded. He was calling the driver, and went to find him. He left her with us and said, ‘Can you watch her?’” Caicedo recalled, laughing.

A man proposing to a woman wearing a
This unsuspecting fiancée-to-be wore a “Just Say No” t-shirt the day her boyfriend popped the question. Vlad Leto

There have also been some wardrobe mishaps, where the unsuspecting fiancée-to-be dresses inappropriately for the once-in-a-lifetime occasion.

“I had a girl in a shirt that said, ‘Just Say No,’” Caicedo said.

“We were all like, ‘Oh my God, how is that possible?’ And the guy organized it in a restaurant and he hired a group of singers and then the whole restaurant was singing. That was funny.”

A heart outlined by candles and string lights, with red rose petals and a bouquet of red roses inside, and illuminated
One woman said “No” after her boyfriend proposed with a candlelit heart. Vlad Leto

In the decade she’s been in business, she’s only witnessed one “No,” during a proposal that featured an outline of a heart on the ground made out of candles.

“He was pulling her in the heart and she was like, ‘No,’ and she left and he stayed there,” she said.

Caicedo said there are women who feel compelled to say “Yes,” since the proposals are so elaborate and photographed — and she eventually finds out they never made it down the aisle.

“Because I follow everyone on Instagram, I see some couples are no longer together,” she said.

“Especially when you’re in public, like Central Park or Brooklyn Bridge Park, there’s a lot of pressure because everyone’s there watching.”

A
Proposal 007 offers a Times Square billboard package that costs $4,200 for 10 minutes. Vlad Leto

Although the company gets special event permits for their park proposals, those only allow you to reserve a spot for one hour — which doesn’t stop pedestrians from ruining the intimate moment.

“I had a guy, it was the 4th of July and literally the second he got on one knee, this guy with a Nathan’s hot dog hat passed by, and I have him on camera, blocking him,” she said.

Their most expensive offering is a Times Square proposal, where the couple’s photos and the words “Will you Marry Me?” are featured on billboards — which costs $4,200 for 10 minutes.

“I had two couples who missed it,” Caicedo said. “They were stuck in traffic.”

The post Falling in love: These NYC marriage proposals flopped— literally appeared first on New York Post.

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