A perfectly picturesque proposal under the bright lights of Times Square in New York City took a terrible turn for the worse when South Carolinian Chasom Wilson fumbled the engagement ring just before popping the question to his long-time love, Kayla Pressley.
This was the small-town couple's first time in New York City and Wilson was not aware of the unspoken rule that proposals and expensive engagement rings should never be exchanged atop a metal sidewalk grate.
Wilson and Pressley were just a few steps from the red bleachers (aka the TKTS Red Steps in the heart of the city) at about 8 p.m. under a light drizzle when Wilson went down on one knee, pulled out a ring box, snapped it open, and watched a princess-cut diamond engagement ring fly out of the box and disappear through the grate.
“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.”
At first, Pressley was not sure why her boyfriend was using the flashlight on his phone to look through the grate, but it soon became apparent that the proposal had gone awry.
But, as luck would have it, Elvimar (Elvi) Rivas and Bertilio Caceres of Con Edison’s Steam Operations were doing routine safety patrols in the area. Wilson flagged down the utility workers in their truck and told them what had just happened.
“We took out a flashlight and we started looking down because we thought maybe it fell in one of our electric manholes," recalled Caceres, senior engineering designer. “We could see the ring, but it was super deep.”
But the duo quickly determined that the structure was not controlled by Con Edison. It was a subway vent operated by the MTA (Metropolitan Transit Authority). The ring had landed on a trash-strewn ledge about 20 feet below street level.
The Con Edison employees told a distraught Wilson to call 311 (NYC's non-emergency number) for assistance, but the deflated beau stated that he couldn't do that because they were returning to South Carolina the next day.
“I knew we wouldn’t get that ring back,” Wilson told The Post. “I said, ‘It’s over with.'”
“The whole weekend I kept thinking about this man's face and this ring,” recalled Rivas, senior analyst. “He was heartbroken.”
So, Rivas and Caceres called 311 on the tourists’ behalf and made it their mission to make sure the ring was rescued and returned to the couple in South Carolina.
On Monday, the pair sought the assistance of higher-ups at Con Edison and eventually an executive who was able to contact his counterpart at the MTA.
Soon after, an MTA Infrastructure Crew arrived at the scene of the loss. Since Times Square is so busy, they waited until the overnight shift so they could shut down the area to safely access the diamond ring.
The MTA team successfully recovered the ring and mailed it back to the couple.
“It made my whole year, just being able to help somebody recover a ring, especially in Times Square,” Rivas told The Post. “That’s near impossible to do.”
Pressley officially accepted Wilson's redo proposal on Stone Mountain in Cleveland, SC. The original ring had not made it to South Carolina in time for the ceremony and she accepted a similar replacement ring. Now she has two and she plans to keep them both.
Pressley told The Post that she believes the engagement happened the way it was supposed to.
“I just felt it was all God’s timing,” she said.
Their wedding is scheduled for May of 2025.
Credits: Couple photo courtesy of Kayla Pressley. Con Edison team (from left to right) Elvimar Rivas, Bertilio Caceres, Peter Knoblauch, Kiara Lebron, and John Masiello. Image courtesy of Con Edison.