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5 Romantic Winter Proposal Ideas

Get creative and surprise your love with one of these romantic winter proposal ideas!

By Kimberly Richmond

Engagement Ideas for the Holiday Season

Proposal season is almost upon us. Don’t get me wrong, there is no wrong time to propose, but one of the first things you learn when you’re planning a wedding is that everything has a “season.”

According to the WeddingWire Newlywed Report, nearly 40 percent of marriage proposals take place November through February. December — particularly Christmas time — is without a doubt the most popular month for “popping the question.” Whether it’s the twinkling lights, the snow flurries, the sparkly celebrations or all of the holiday festivities, the stage practically sets itself for a movie-worthy proposal.

If you’re planning on adding a little “bling” to your season with a holiday engagement, here is a roundup of winter proposal ideas that are sure to provide a beautiful start to your happily ever after.

1. The Surprise Visit

I’m a total sucker for surprises, and when it comes to an occasion like this, don’t you want the element of surprise?

Photo Credit: Unsplash

The holidays usually mean traveling home to see family, and often, they can be spread far apart from one another. Whether you’re loading up the car and driving to Upstate New York to spend the holidays with your soon-to-be fiancé’s parents or hopping on a cross country flight to spend Thanksgiving with yours, chances are you’re spending them together. The “surprise visit” proposal shakes things up and is the perfect scenario for couples who want to include their families in their special moment.

You could invent a last minute, bogus “work emergency,” which wouldn’t allow you to spend the holiday with your partner. While this might cause some turmoil and tension in the short term, I promise it will be worth it in the end. Once your beloved has made it safely to their family where they will be spending the holidays (“leaving” you miles behind), the look on their face when they answer the knock on the door only to find you there — on bended knee will be priceless. The best part about a holiday proposal is getting to celebrate with family afterwards.

2. Let it Snow

There is something whimsical, romantic, and downright magical about snow because it seems to bring out the inner child in all of us. It also provides scenarios for a spectacular, unforgettable, and fun proposal.

How about getting creative and building a snowman with “arms” sturdy enough to attach a ring box to? Or how about engaging (no pun intended) in a good, old fashioned snowball fight? Surprise your partner with a ring when they turn around to toss an epic snowball. What’s that I said about bringing out your inner child?

Photo Credit: Unsplash

There’s no denying that there is something extra captivating about the first snowfall of the season and it’s such a sensational view to wake up to. Write your proposal in the fresh fallen snow in big, bold letters so that it’s the first thing your partner sees when they wake up and look outside. Naturally, this should be followed by breakfast in bed!

3. Winter Getaway

It doesn’t get much more romantic than snuggling up by a roaring fire, tucked into a cozy mountain lodge, with a good bottle of wine, and a blustery snow storm roaring outside. A winter getaway can set the scene for an uber romantic proposal idea that can turn into a weekend-long celebration. If you’re the adventurous type, imagine the adrenaline rush of proposing at the top of a snowy mountain peak.

Or, how about popping the question on a ski lift or while dog sledding? Even if mountain sports aren’t your “thing,” mountain ranges are almost always synonymous with postcard-like towns that come to life during the holidays. A candlelit dinner in an old tavern along historic Main Street while taking in the magnificent snow-capped landscape isn’t a terrible setting either. Top that off with a moonlit sleigh ride and you’ve got yourself a pretty unforgettable winter proposal.

Photo Credit: Unsplash

4. The New Year’s Eve Proposal

New Year’s Eve is quite possibly the most perfect scenario for an unforgettable proposal. Whether you’re throwing a NYE party, celebrating on the town with friends, or have a romantic dinner for two planned — chances are, you will be in a festive mood, dressed to the nines and ready to celebrate. If you decide to propose at a New Year’s Eve party, enlist the help of your guests.

Photo Credit: Unsplash

I can think of few things more electrifying than a room full of people counting down to midnight and then stopping at “three” so that you can get down on bended knee and propose at the stroke of midnight. Not only will you have an amazing anniversary to celebrate every year, but you’ll have fireworks to go along with it! A New Year’s Eve proposal doesn’t have to involve a big group.

If you’re anything like me, I enjoy ringing in the New Year from the coziness of my home, away from the crowds. Plan a romantic evening in and suggest to your partner that you share your New Year’s Resolutions with one another. Make the final resolution on your list the resolution to spend the rest of your life with your partner. Whether you chose to do your resolution “reveal” before or after the ball drops is up to you — the champagne will be on hand either way!

5. Christmas Proposal

Pre-COVID, Christmas Day was the most popular day of the year to get engaged. While it’s dropped to number three (following Valentine’s Day and New Year’s Day), this jubilant holiday remains a favorite day to pop the question. The joy of the season, the parties, the mistletoe, the eggnog, and overall holiday cheer all serve as the perfect inspiration to ask that very important question.

Photo Credit: Unsplash

One of the beautiful things about the season are all the fun elements leading up to Christmas Day, giving you so many opportunities to get creative. While classic, putting the ring under the tree isn’t the only way to go. I’m a total sucker for a good stocking-stuffer, and while I would hardly call an engagement ring a stocking-stuffer, I love this idea!

I also love a good advent calendar — especially a personalized one that ends with a proposal. Whether you’re hiding the ring box in the tree, hanging the ring from Mistletoe, or engraving your question on an ornament — a Christmas engagement is nothing short of magical.

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