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Rules of Engagement—Tips for a Perfect Proposal

proposal tips

Ever hear of proposal season? While couples definitely get engaged all year long, there is a real uptick in proposals during the period from Thanksgiving through Valentine’s Day—about 40 percent of proposals happen during that time, according to “I think it’s because it’s a time for family filled with joy and love; a time of coming together to enjoy the important people in your life,” says Kristen Estela of Lovely Event Planning, based in White Plains, NY. If you’re thinking about taking that next step in your relationship, read on for tips to help you plan the perfect proposal—including some gorgeous engagement ring picks—and guidance on what to do first (once your partner says yes).

Get Creative with the Location

Popping the question in a place that’s meaningful will make the moment even more
memorable. “Meg played college softball and it was a huge part of her life,” says Estela,
recounting a friend’s engagement. “At a softball game with her old teammates, Joe arranged to propose right on the field in front of everyone. It was super romantic for everyone to see and share in their celebration.” Another couple got engaged on a trip that marked the beginning of a new tradition: “After hiking through the night in Machu Picchu, they arrived at the Sun Gate at the break of dawn, and he proposed,” says celebrity wedding planner Brian Worley. “Now they’ve made it their mission to visit all the Wonders of the World.”

proposal tips

Involve Your Family

If you’re on the traditional side, you’ll probably ask your partner’s parents for their blessing before proposing. But why not take it a step further and invite them to be a part of the day? Bruce Plotkin, a Weston, CT-based photographer, captured the proposal of one man who flew his soon-to-be-fiance’s parents out from the west coast for the occasion. “He asked her to marry him by the water in Bridgeport, and meanwhile the parents were hiding in their cars,” he says. “When they popped out afterward to toast the couple with champagne, she was totally surprised.” Estela worked with another couple who got engaged while on vacation with his family—but he also sneakily invited his fiance’s family to celebrate with them over the weekend. 

proposal tips
Will proposed to Aly on Block Island—and even invited her parents as a surprise.

Hire a Photographer

Having a hidden photographer or videographer to capture the emotion of the moment can be well worth the investment. “It’s one of those memories you’ll watch over and over—maybe more than your wedding video if the surprise element is really there,” says Worley. And when you hire a photographer, take advantage of their expertise to ensure the photos turn out well. “Get them involved in decisions like the time of day and the location,” says Plotkin. They’ll think of details you might not, like that the light at high noon may not be so flattering, or that a Central Park proposal will mean strangers in the background of your photos.

proposal tips
During a sunset beach walk in Kennebunkport, Ben asked Julie to marry him.

Set the Scene

All you really need is a ring and a few heartfelt words, but the right backdrop can make your proposal even more special. “One couple I worked with really loved Disney, so Andrew asked a theme park photographer to take their picture right in front of the Cinderella Castle,” says Estela. Right then, he got down on one knee, and the pair got an amazing photo. Custom props are another sweet way to add to the scenery. Plotkin photographed a beachside proposal where the groom-to-be set up a hand-painted sign with the meaningful places the couple had been—including one lettered “Will you marry me?”

proposal tips
Max popped the question to Lindsey on Compo Beach in Westport.

Make It Yours

Remember, however you decide to pop the question, it will be a special, emotional moment—so don’t feel like you have to create the next viral proposal video to make it meaningful. “It doesn’t have to be a big, extravagant undertaking, it just has to come from the heart,” says Estela.

Engagement Rings We Love
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