Make Your Question Pop!

Asking someone special to spend the rest of their life with you is one of the most memorable moments of your life. Here are some local gentlemen who popped the question in fanciful, romantic and certainly unforgettable ways.

Grant Gyesky took his proposal to new heights when he asked Mia Perovetz to marry him at Mount Arenal in Costa Rica. After Mia said, “Yes!” they slid down the earth- carved water slides into the natural hot springs. (Greenwich Magazine, January 2010)

James Bradley convinced Rebecca Babcock to join him in on a vacation for Christmas. Rebecca worried she’d feel homesick for her family on Christmas Day until Jimmy proposed to her on a private beach in Hawaii on Christmas Eve. Talk about a perfect Christmas gift. (Greenwich Magazine, January 2010)

Kent Dresser knew he wanted to sail into the future with fellow avid sailor Meaghan McCarty. So he surprised her, after she sailed in the 2008 Newport-Bermuda Race, by flying to Bermuda and proposing under a starlit sky at the Reefs Hotel. (New Canaan-Darien Magazine, January/February 2010)

Jeremy Cole decided to take the plunge literally when he proposed to Shannon Simpson while they were on vacation in Florida. Jeremy gave Shannon the engagement ring he designed while they swam in the ocean! After she said, “Yes!” they went on a romantic dinner cruise Jeremy had planned. (New Canaan-Darien Magazine, November/December 2010)

Andrew Schoff and Heather Smith’s dog, Claybin, played a pivotal role in Andrew’s proposal. The couple often joked about Claybin’s last name. Heather said his last name would be Schoff when she became a Schoff, too. So when Andrew decided to propose he had a special dog tag engraved with “Claybin Schoff” and attached the ring to the tag on the dog collar. Claybin woke up Heather, showed off his new collar, and then she saw the tag and the ring! (New Canaan-Darien, November/December 2009)

Matthew Evan Smith enlisted a trusted neighbor to help with his proposal to Jessica Lee Richman. One evening after a walk through Battery Park in New York City, they returned to their home to find it filled with flowers, candles and a bottle of Champagne. With the scene set for romance all Matthew needed to do was ask the question. (Westport Magazine, November/December 2009)

Patrick Leahy hid the engagement ring in his girlfriend, Jennifer Kinberg’s, bag planning to surprise her after a day of sightseeing while on vacation in Hong Kong. Jennifer discovered the ring box before they even left the hotel so Patrick quickly got down on one knee and proposed right there. (Greenwich Magazine, February 2010)

Conor Flynn struck a pose when he proposed to Meredith Eves. While vacationing in Paris they took a walk in the gardens of the Rodin Museum and Conor mimicked “The Thinker” sculpture. While Meredith was pulling out her camera to capture the funny scene, she looked up to find Conor on one knee with a ring. (Greenwich Magazine, February 2010)

Tell us your engagement story, comment below!

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