New Yorkers helped a South Carolina tourist get his marriage plans back on track after he bungled his surprise proposal — by dropping the engagement ring down a sidewalk grate in Times Square.
Chasmon Wilson’s nightmare began at 8 p.m. on a rainy Saturday in March when the truck driver brought his girlfriend of eight years, Kayla Pressley, to the Crossroads of the World to propose to her with a $1,600 princess-cut diamond, white-gold engagement ring.
As Wilson produced the small Kay Jewelers box, the ring suddenly popped out and fell through a sidewalk grate, falling 20 feet below ground to a trash-strewn ledge.
“It was like everything moved in slow motion,” Wilson, 33, told The Post. “I was in disbelief that this is what we came to New York for and it fell through. I felt like the worst man on the planet Earth.”
Wilson said he had planned to propose more than 1,000 feet above Midtown at One Vanderbilt, with its panoramic views, but got “cold feet” when he saw the crowds. He pivoted, opting to propose in Times Square.
Pressley had no idea this was the big day after nearly eight years together, and she missed the ring slip, as she was putting their umbrellas down.
“When I turn around, he’s on the ground looking with the flashlight on his phone,” Pressley, 29, said.
He initially told her he dropped the hotel key card, but between his dramatic reaction and effort to retrieve it, Pressley realized it was her engagement ring.
By sheer luck, a Consolidated Edison truck passed by and Wilson flagged it down.
“We got out, we looked where he dropped his ring to see if it was a Con Ed structure and what we found it was the [Metropolitan Transportation Authority’s] structure,” said Elvimar Rivas, a senior analyst at Con Ed.
Wilson wasn’t optimistic.
“I knew we wouldn’t get that ring back,” Wilson said. “I said, ‘It’s over with.’”
He, Pressley and their kids, Grayson, 7, and Skylar, 6, returned home to their 3,837-person town of Roebuck, SC, the next day.
Unbeknownst to the couple, Rivas reached out to the MTA after the weekend and hatched a plan to rescue the ring.
“It was in my head all weekend . . . he was broken-hearted,” Rivas, 40, recalled of Wilson.
A crew of five was sent to survey the situation and another crew of five to retrieve the bauble below Seventh Avenue near West 46th Street. The job had to be done overnight to avoid any disruptions from pedestrians and traffic.
“It made my whole year, just being able to help somebody recover a ring, especially in Times Square,” Rivas said. “That’s near impossible to do.”
Wilson got a text message about a week later that the ring had been recovered.
By the time the ring arrived in South Carolina, however, Wilson had already bought another, slightly different, ring, and proposed to Pressley on April 27 — far away from a sidewalk grate.
He finally popped the question atop Stone Mountain in Cleveland, SC.
Pressley, a registered nurse, said, “Yes.”
A religious couple, they now believe the engagement happened the way it was supposed to.
“I just felt it was all God’s timing,” said Pressley, who plans to keep both engagement rings.
To avoid any other mishaps Wilson is taking a backseat until their special day on May 24, 2025.
“I’m not handling the wedding plans at all,” he said.
