12 Holiday Proposal Ideas That Will Guarantee a YES!


Updated 11/29/18

T-REX & Flower / Stocksy United

Oh, the holidays! Full of merriment, families, decorations, and plenty of proposals. If the most wonderful time of the year doubles as your idea of the best moment to pull out a ring, you’re not alone. It’s the most popular season to get engaged. That also means creativity is of the utmost importance, since well, a holiday engagement is the theme of many a rom-com. There’s always the box within a box idea—watch the Christmas classic Serendipity for inspo—but likely, you want something your future spouse hasn’t seen before that also stays true to your own traditions. That means no cheesy romantic gestures like the cue cards from Love Actually or getting down on one knee by the fireplace with chocolate-covered strawberries and Champagne. To help you take it up a notch, here are 12 ways to propose this holiday season.

01 of 12

Make it personal

dog ring bearer

Photo by Valorie Darling

Opt for something more authentic than the protocol of a Colin Firth film. “It'll be easy to pick an incredible spot to pop the question since most of the world will be one beautiful backdrop for the big moment, but think of something memorable to express how much love and thought is going into the moment itself,” explained Tommy Waters of The Renaissance in Richmond, Virginia. He suggests choosing the location and timing based on your past holiday memories, even if it’s something as simple as shopping for decor or walking your pup around the neighborhood one holiday morning. “Be as organic as possible,” Waters says.

02 of 12

At the Christmas tree farm

Kate Brewer

Dozens of photos of proposals surrounded by Douglas firs exist, which only proves this is one iconic holiday moment for popping the question. But don’t just show up without a game plan and hope for the best, says Heather Vaughn, founder of proposal planning company The Yes Girls. Organize the exact spot with the owners of the farm before you set foot there on the big day. You can even select the tree, purchase it, then decorate it to mark it as the one. The next day, dress in your best rustic attire and be sure to let your SO know to don a cozy sweater and warm winter hat too, as you’ll be shopping for this year’s tree. If friends or family tag along, designate one as the photographer or videographer. When you happen upon the clearing and the tree, ask for his or her hand in marriage. “Playing off a tradition as you would normally do is an easy way to get your significant other to a location without setting off suspicion,” she adds.

03 of 12

Under the mistletoe

<p>Couple Kissing Under Mistletoe</p>

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Plenty of carols speak of a mistletoe, but how often do you actually see one hanging for a kiss? Source fresh mistletoe from the local Christmas tree farm and hang it from a doorway, branch outside, or rafter where there is a handsome backdrop (for the photos, obv!). Lead your soon-to-be fiancé to the spot where you can act like it’s a normal kiss, thanks to the holiday plant. But before you give her or him a peck, pop the question.

04 of 12

As a riff on the 12 days of Christmas


We all know the beloved carol, so what better way to create an unique proposal than by personalizing the day to your love story? Brainstorm 11 gift ideas for your SO, one for each day leading up to day 12, when you’ll pop the question. They can be physical items, like her favorite candle or his favorite candy. Alternatively, pick 11 nostalgic moments from your relationship to share in a thoughtful way, such as a poem or heartfelt letter, before adding the new memory to the list.

05 of 12

On New Year’s Eve...while you get ready

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There are few things more cliché than taking a knee as the ball drops in Times Square on your television, so challenge your ideas of a perfect NYE proposal. Pick a moment when your SO least expects it: as you’re primping. Before you go out on the town, add an accessory to her glam look. Tell her she needs extra glitz for the sparkly holiday, then present her with the rock. It works for proposing to guys as well, since there is no such thing as too much shimmer as you countdown to midnight. Don your best cocktail or black tie attire and celebrate, one glass of Champagne at a time.

06 of 12

With the Wishbone at Thanksgiving or Christmas


Do you know the tradition of breaking the wishbone from the turkey? It’s when two people pull on opposites sides of the inverted-V-shaped bone from the bird. It will eventually snap, and the longer side wins. It’s a popular game with the kiddos, but it can also serve as the perfect moment for a proposal—whether you capture victory or suffer defeat. If the recipient wins, tell him or her that you’re sure to make the dream come true. Then take a knee and pull out the ring. If you win, tell your SO that your wish is to be together forever and open the jewelry box. How’s that for getting the best of both scenarios?

07 of 12

While brunching on New Year’s Day

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January 1 may be the year’s laziest day—cue football games on television and loungewear—so make it exciting by saving the ring and the big question for the morning’s brunch. If you plan to hit your favorite breakfast spot, organize with the restaurant ahead of time. (We have some great tips here!) At home more your style? Fry up eggs and bacon, then pop some bubbles as you pop the question. Just note that this may not be the best idea if you plan to be hungover!

08 of 12

At Rockefeller Center in New York

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What’s better than popping the question in front of the most famous Christmas tree? Plan an evening to visit the iconic decoration, complete with hot chocolate to gaze upon the lights Rockefeller Center. Not near New York City? No problem. Most town centers erect their own large tree, so make a date to watch the local lighting or wander the town square. When the moment strikes (or, as the lights come on), it’s your indication to pull out the ring. Just note this is likely the idea of another crafty proposer, so be sure to secure a reservation or stake out a spot early.

09 of 12

On Christmas morning in bed

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Forget wrapping the ring as gift or stuffing it in an obvious place like a stocking. Instead, keep it intimate and casual by rolling over for snuggles and that infamous question before you head to breakfast. For an extra surprise, stock the fridge with mimosa or Bloody Mary supplies. Waters suggests surprising your families to increase the celebration. Don’t tip them off to the plan, so when you roll down downstairs in your pajamas donning a brand new rock, they’ll be overjoyed. Then it’s time to toast with the breakfast cocktails.

10 of 12

During a holiday card photo shoot

Photo Courtesy of Etsy

This idea is perfect if you want a professional photographer involved—snap your proposal moment and print it on your holiday correspondence! Schedule a session and plan to pop the question mid-shoot, says photographer Emilia Schobeiri of Emilia Jane Photography. Let your photographer in on the secret. As a pro, they’ll help you select a photogenic backdrop for the big moment. Agree on a cue for the photographer so that on the day, you can give the signal that you’re about to do the deed. As you’re posing for the next frame, quickly drop to one knee to surprise your significant other with the life-changing question. Worried your SO will be suspicious of the shoot? “Say you’ve won a photoshoot through Instagram,” Schobeiri explains, noting that plenty of photographers do contests on blogs and social media to promote new services or kick off the holiday season.

11 of 12

With Christmas lights as your backdrop


If your town is anything like ours (and Home Alone), your neighbors get into the holiday spirit by covering their homes in lights and inflatable Santas. Plan a tour to gaze at the decorations, ending at what you deem the most well-lit home. One evening, take your soon-to-be-fiancé on a walk or drive. When you arrive to “the house,” propose with it as your backdrop.

12 of 12

Hanging as a Christmas ornament


This is not entirely original, but we do find it to be extremely sweet. Tie the ring to a pretty ribbon and hang it from the tree among the shiny ornaments. Jamie Chang of Mango Muse Events in San Francisco suggests turning it into a scavenger hunt by giving your SO a card with a clue to search the pine. It can even be multiple hints including a few different ornaments. When he or she finally discovers the ring, drop to one knee.

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