A South Carolina tourist’s marriage proposal in Times Square turned into a nightmare when he accidentally dropped the engagement ring down a sidewalk grate. Chasmon Wilson had planned to surprise his girlfriend of eight years, Kayla Pressley, with a $1,600 princess-cut diamond ring.
The mishap occurred on a rainy Saturday evening in March. Fortunately, New Yorkers came to his rescue, helping him retrieve the ring and get his proposal plans back on track, as reported by the New York Post.
Wilson recalled recently that he fumbled with the engagement ring, which fell through a sidewalk grate and landed 20 feet below on a trash-strewn ledge.
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“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.”
Initially, Wilson intended to propose at One Vanderbilt, which is high above Midtown and has panoramic views. However, he changed his mind due to the large crowds and decided to propose in Times Square instead.
Pressley was unaware of Wilson’s surprise proposal as she was busy with their umbrellas when the ring fell.
“When I turn around, he’s on the ground looking with the flashlight on his phone,” Pressley, 29, said.
Initially, Wilson told her he had dropped the hotel key card. However, his dramatic reaction and frantic attempts to recover the item led Pressley to realize it was the engagement ring he had intended to use for his proposal.
By chance, a Consolidated Edison truck drove by, and Wilson managed to flag 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.’
The next day, Wilson, Pressley, and their children, Grayson, 7, and Skylar, 6, returned to their hometown of Roebuck, SC, which has a population of 3,837. After the weekend, Rivas contacted the MTA and devised a plan to recover the ring, unbeknownst to the couple.
“It was in my head all weekend . . . he was broken-hearted,” Rivas, 40, recalled of Wilson.
A ten-person team was dispatched to address the situation: five to assess it and five to retrieve the ring from below Seventh Avenue near West 46th Street. The operation was conducted overnight to minimize disruption to 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.”
About a week later, Wilson was notified that the ring had been recovered. By the time it reached South Carolina, Wilson had already purchased a new, slightly different ring and proposed to Pressley on April 27.
He chose a more picturesque setting, proposing atop Stone Mountain in Cleveland, SC, instead of near a sidewalk grate. Pressley, a registered nurse, said, “Yes.”
The couple, who are religious, now believe that everything that happened was meant to be.
“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.
