After a tourist from South Carolina botched a surprise proposal by dropping his engagement ring on a sidewalk grate in Times Square, a New York resident helped him get his wedding plans back on track.
Chasmon Wilson's nightmare began at 8 p.m. on a rainy Saturday in March, when the truck driver took his girlfriend of eight years, Kayla Presley, to Crossroads of the World and proposed to her with a $1,600 princess-cut diamond and white gold engagement ring.
Wilson removed a small Kay Jewelers box, and the ring suddenly shot out, fell through a grate in the sidewalk and onto a trash-strewn shelf 20 feet underground.
“Everything seemed to be moving in slow motion,” Wilson, 33, told The Washington Post. “I couldn't believe this was what we came to New York for, and it had all failed. I felt like the worst man on the planet.”
Wilson had planned to propose at One Vanderbilt, more than 1,000 feet above Midtown Manhattan, with panoramic views, but was “daunted” by the crowds, so he changed plans and proposed in Times Square.
Presley had no idea that it would be a big day after nearly eight years of marriage, and ended up missing the ring exchange when he put his umbrella away.
“I turned around and he was on the ground looking at me with the flashlight on his phone,” Pressley, 29, said.
He initially told her he had lost his hotel key card, but his dramatic reaction and efforts to retrieve it led Presley to realize it was her engagement ring.
By sheer luck, a Consolidated Edison truck drove by and Wilson waved it down.
“We went out and checked to see if the place where he dropped his ring was the Con Ed building. And it was [Metropolitan Transportation Authority’s] “It's a complicated structure,” said Elvimar Rivas, a senior analyst at Con Ed.
Wilson was less optimistic.
“I knew I wasn't going to get that ring back,” Wilson said. “I said, 'That's it.'”
He and Presley, along with their two sons, Grayson, 7, and Skyler, 6, returned to Roebuck, South Carolina, a town of 3,837 people, the next day.
Unbeknownst to the couple, Rivas contacted the MTA after the weekend to make plans to salvage the ring.
“It was on my mind all weekend… He was heartbroken,” Rivas, 40, said of Wilson.
Five crews were sent out to assess the situation and another five were sent to salvage the decorations below Seventh Avenue near West 46th Street. The work had to be done overnight to avoid disruption from pedestrians and traffic.
“Just being able to help someone get their ring back, especially in Times Square, has made this year the best one yet for me,” Rivas said. “That's almost impossible to do.”
Wilson received a text message about a week later saying the ring had been recovered.
But by the time the ring arrived in South Carolina, Wilson had purchased a slightly different one, and on April 27, he proposed to Presley, far from any sidewalk grating.
He finally proposed at the top of Stone Mountain in Cleveland, South Carolina.
“Yes,” said Presley, a registered nurse.
As a religious couple, they now believe their engagement took place the way it was meant to be.
“It all just felt like God's timing,” said Presley, who plans to keep both engagement rings.
To avoid further mishap, Wilson is waiting until May 24, 2025, a special date.
“I'm not involved in the wedding planning at all,” he said.
