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This Surprise Madison Square Park Proposal Was Almost Ruined by Two Guys Just Trying to Do Their Jobs

This graphic designer’s boyfriend had the perfect ploy in place: A romantic stroll in the park—what could go wrong? But just before he could pop the question, security guards stepped in.

Associate Digital Editor
Photography by: Max Wanger

In the summer of 2009, somewhere along I-95 between Baltimore and Brooklyn, graphic designer Katie Evans began to suspect she wanted John Reeves to be her copilot for longer than just the drive to New York City. The two met through a mutual acquaintance in their home state of Florida when Katie was in high school and John was in college. They were friends throughout her college years, but by the time they talked about dating, “I was going to New York for a job,” she says, “and John was still studying in Florida, so we said we’d wait until he graduated.” In the meantime, he agreed to help her move. It was in the U-Haul, she recalls, that “I said I wanted him to be my boyfriend—right then.”


The first year, they had a long-distance relationship. “I’d come up to visit, and we’d meet in Madison Square Park, near her office,” says John, now a sales manager. Their park dates became a tradition, and one year after John followed her to the Big Apple, he knew it was where he wanted to propose. 


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Photography by: Joseph Guertin

On a blustery fall day in 2011, he managed to get Katie to join him for a walk there by insisting on a lunch at Shake Shack. “He was being so strange, and I started to wonder if he was trying to plan something,” Katie recalls. But when she kept pressing the point, John said, “Stop questioning me; I just want to go!”


Burgers and fries in hand, John suggested they go sit on a particular bench—the one where they used to meet when they were dating long-distance, and the one John had instructed their friend Joe, hiding nearby with a camera, to focus on. Only, Katie didn’t want to sit there. Being cold, she said she’d rather sit by the heaters (“I was just really messing it up like the whole day,” she laughs), but she went along with him anyway. 


When she realized that bench was right by a garbage can, she insisted they switch to a spot a few benches down, and Joe adjusted his position to capture the moment. 


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Photography by: Joseph Guertin

John was just launching into his speech about love and their relationship when park security came over to warn the pair that someone was taking their picture. “I was shaking my head, trying to cut the guys off,” John says. Luckily, Katie didn’t catch on, instead assuming someone must be snapping photos of the hawk they had seen earlier flying around with a mouse in his mouth. The guards retreated, leaving John finally free to get down on one knee and say, “I want to be with you forever; will you marry me?”


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Photography by: Joseph Guertin

“Yes,” Katie said, through tears of joy. “After he put the ring on my finger, I was like, ‘I can’t see it’—my eyes were so watery and blurry.”


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Photography by: Joseph Guertin

Shortly after, the security guards returned and apologized for almost ruining the moment. “Let us be the first to congratulate you,” they said. Katie was confused about what they meant, so John explained that their friend Joe was the man behind the tree and he really was taking pictures of them.

Photography by: Joseph Guertin

Katie’s takeway: “If you’re getting vibes that your boyfriend is about to propose, don’t give him a hard time. I was challenging John a lot throughout the day to mess with him, but looking back, I should’ve just gone with the flow.”


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