5 Sweet Proposal Stories from New York Couples

New York-based to-be-weds share their romantic tales of engagement.
by Rachel Sylvester
  1. Tiffany & John

    central park carousel engagement shoot
    Great Romance Photography


    While visiting family in California, Tiffany woke up one morning to join a friend on a sunrise hike along the beach. But as they approached the water, Tiffany noticed an unexpected visitor waiting in the sand. “When I saw John, my heart dropped," she says. After leading Tiffany to a candlelit picnic, John pulled out a homemade scrapbook before asking her to be his wife. “The sweetest part was he had planned an after-party with all of my closest California friends whom I hadn't seen in years," Tiffany says. “He made a huge effort to get them all in the same place." The ring: Custom

  2. Lauren & Josh

    brooklyn boathouse engagement shoot
    Melissa Kruse Photography


    Two years after they met, Lauren and Josh traveled to Iceland to take in the Northern Lights. Soon after getting off the plane, Josh realized he left his bag— and, more importantly, the ring—on the airport shuttle bus. “Fortunately, I was able to sprint after the bus and get it back," he says. The pair visited the Gullfoss Waterfall on a sightseeing tour, and Josh anchored his camera in the snow to snap a photo. “I told Lauren I wanted to be with her forever, and her immediate response was, 'Are you kidding me?' " Josh says. “If you watch the video, it's hard to believe she even said 'yes' based on her physical reaction." The ring: Brian Gavin Diamonds

  3. Chaz & Grant

    brooklyn engagement shoot
    Sincerely, Emma


    Shortly after a dating website determined they were 99 percent compatible, Chaz (left) and Grant met over burgers and beer in Madison Square Park. “We fell fast and hard for each other," Chaz says. Four years later, the couple spent a routine Saturday at a yoga class before taking their dog, Gracie, on an afternoon walk. “I asked Grant to spend the rest of his life with me on the corner of State and Hicks," Chaz says of proposing in their Brooklyn Heights neighborhood. “I think Grant took the ring out of my hands before I could get the words out of my mouth!" The ring: Tiffany & Co.

  4. Chinny & Chike

    brooklyn engagement shoot
    Emma McDonald Weddings


    An impromptu trip to St. Maarten and a well-placed engagement ring resulted in a proposal neither Chinny nor Chike will forget. “Looking back, the signs were there," Chinny says. “He was even willing to take lots of cheesy selfies with me without protest." One night, after returning to their room, Chike stashed the ring under Chinny's pillow without first considering how he'd get her to find it. “We were chatting and he randomly brought up that there might be bugs in our bed, so we'd better check under the covers," Chinny says. “I lifted up my pillow, and there it was." The ring: James Allen

  5. Jackie & Zach

    central park engagement shoot
    Little Apple Photography


    With plans to shop for an engagement ring the following weekend, Jackie and Zach set out to purchase their first Christmas tree together. But as the two searched for the perfect pine to bring home for the holidays, Zach let Jackie know they wouldn't be ring shopping any time soon. “He asked, 'What would you do if I already bought one and it's in my pocket?' " Jackie recalls. That's when Zach dropped to one knee. “I had tree-cutting gloves on, so it took a moment before could I toss them over my shoulder and put the ring on!" The ring: Lauren B Fine Jewelry and Diamonds

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