Diamonds in the rough
January 28 • 2011

When a man pops the question, it’s an unforgettable moment he and his beloved will cherish for the rest of their lives. But some proposals are so memorable that they capture the hearts of even total strangers. Here’s a roundup of some of the most remarkable, headline-grabbing proposals from the last year (no pressure, fellas):
Endearingly geekiest: Brian Haggerty, an employee of LinkedIn, developed an iPhone app for his elaborate proposal to his girlfriend Jeannie. The treasure hunt app sent his soon-to-be fiancee around a heart-shaped route throughout San Francisco. After she solved all of the video clues, Jeannie found Brian waiting on a hilltop ready to propose.
Best choreographed: A guy brings his beloved to Madison Square Park in New York under the guise of a romantic afternoon stroll. They stumble upon a “documentary film crew” and he agrees to be interviewed, while she waits nearby. What follows is an expertly orchestrated testament of love, complete with singing and dancing by the love-struck guy and a bunch of his pals, “He hearts you” T-shirts, and even a few back flips. Watch the whole thing here.
Jim Henson-iest: Meet New Hampshire photographer Sid Creaser, also known as “the Muppet proposal guy.” Sid, a huge Muppet fan, proposed to his longtime love, Sara, with the help of two Muppet dolls he secretly created in their likenesses at an FAO Schwartz workshop. Sid then filmed a movie trailer about his relationship with Sara with the Muppets as stand-ins, and arranged for a local movie theater to play it after a lineup of three real film trailers. Sid and Sara sat down for the show, while their family and friends snuck in behind them, and a surprised Sara watched the proposal unfold on the big screen. Check out the trailer and a detailed account by Sid here.
Most heart-stopping: Matt Cawley had arranged to propose to his girlfriend, Stacey Scanlon, on a jetty overlooking the water in Cape Cod, but his romantic plan went horribly, unexpectedly awry. The $9,000 diamond ring he’d purchased for Sara came loose as she picked up a sand dollar he’d tied it to, and tumbled into the surf below. Four frantic hours of searching were fruitless, and Matt and Sara headed home. But here’s the happy ending: Matt proposed in the car, Sara said yes, and they later discovered that Matt’s pragmatic mother had insured the ring in full. And mothers-in-law get such a bad rap.
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