In the summer of 2014, Abbey Lipson and Jeffrey Silver swiped right on each other on the same dating app. Their relationship started off slow—in part because of Abbey’s long work hours at the time—but once it started picking up speed it just never slowed down. Two years later, Jeffrey took Abbey out to dinner at their favorite French restaurant in their New York City neighborhood. There, Jeffrey announced he had planned a surprise weekend getaway. The pair had been discussing an engagement for some time and Abbey knew he was working on the ring, but the
groom-to-be knew he had to deceive her so she didn’t see the proposal coming. “I’m a hopeless romantic and wanted to do something over the top,” says Jeffrey. So, off to Mohonk Mountain House in the Catskills they went.
Upon arrival, they decided to go on a hike. He was nervous, and she kept stopping at gazebos and other viewpoints. “I was over the moon to just get away from the city and be out in nature,” Abbey says. “I was soaking everything in and actually told Jeffrey that it was too bad the ring wasn’t ready because this would be the perfect place to propose.” As they approached the summit, he spotted a sky tower and knew that’s where he knew he wanted to pop the question. Abbey ran ahead of him where she once more was taken aback by the views and scenery—not noticing Jeffrey behind her, down on one knee. She didn’t turn around until he said, “Hey Abbey…” and that’s when she spun to see him, the diamond-ring glistening in the sunlight, and then started bawling. The question was asked, the answer was given, and they celebrated with a picnic, a spa trip, and some horseback riding.
Eighteen months later, they went to another equally spectacular setting for their destination wedding—Montego Bay, Jamaica. On December 3, 2017, with 87 loved ones in attendance, they tied the knot at Round Hill Hotel & Villas, a spot that inspired the design of the day. Graphic stripes, tropical prints, dark wood, and a pineapple motif were used throughout the event. As for the mood? “It really felt like we were on vacation with all of our closest friends and family and a wedding was just thrown into the mix,” says Abbey. “Everyone was there to celebrate us and at the end of the weekend no one wanted to go back to reality. It was a surreal, dreamlike fantasy.”