10 Killer Proposal Ideas to Get Engaged This Winter

December 4, 2020

It’s the most cozy, warm, romantic time of year. It’s engagement season! Wedding bells are definitely in the air as proposals are happening like chimney fires on a cold, snowy night. So if you want to get engaged this winter and need some fun inspiration for getting down on one knee, read on!

1. The Christmas Gift

Maybe it’s cliche, but when you spend so much on such a small, long-lasting item, what better holiday to give it to your special someone?! You’re already surrounded by friends and family (or are seeing them soon!), so pop that question and make your moment merry and bright! Can you think of a more perfect stocking stuffer?

2. By the Fire

Is the fire as delightful as the weather is frightful? You could make it that much more delightful by taking advantage of the flames you’ve kindled in your fireplace and feeding the sparks between the two of you. Get down on one knee within the warm glow and comfort of your fireplace!

3. On the Slopes

Think you two are too adventurous for Winter to be romantic? WRONG. Hit the slopes! Whether you’re snowboarding or skiing, you’ll be planning your wedding by the time you’re down the mountain!

4. In the First Snow

The first snow is often coined as “magical”. Which is also often the feel soon-to-be-engaged couples strive for to make the dating to engaged transition – *cough cough* the proposal. Whether you’re wearing PJs while enjoying the falling snow or building a snowman that may need a ring, I can’t think of a moment in that first snow that wouldn’t be perfect.

5. Romantic Carriage Ride

If it’s in the movies AND her Pinterest feed, it may be perfect. If you’re after a picture-perfect, Hallmark movie moment, a beautiful carriage with a pair of gorgeous horses is your key!

6. Hot Chocolate

Winter is the season for warmth – whether that’s by bundling up or drinking liquids to warm you up from the inside-out. Why not write at to bottom of their mug, “Marry Me” to catch them off guard and all warmed up?!

7. Famous Locations

Make the setting you get engaged as breathtaking as the engagement itself! Visit some of the world’s most sought-after places like New your, Switzerland, or Northern Lights viewing locations. After COVID, of course.

8. Throw a Christmas Party (That’s Actually A Surprise Engagement Party)

A small, private engagement isn’t everyone’s jam. Surround yourself with friends and family through a “Christmas party” that will soon turn into a surprise engagement party after the question is officially popped!

9. DIY Advent Calendar

There are so many special days in December – no matter the holiday you’re celebrating… pick one to make it the “big day”, throw a ring in there and fill the rest with chocolate. On December 1st, have her open the first and let the countdown begin!

10. Ice Skating

If you’re looking for an engagement plan that’s understated, yet sweet and very fun, ice skating is such a fun way to celebrate what the season brings! It’s a fun, fairly common date night, so it won’t cause suspicion, and the creative scenes that ice skating rinks put on during the holidays will make your special moment picture-perfect.

Speaking of picture-perfect, I LOVE engagements here at Jimmy Song Weddings and would love to shoot your dream engagement this winter to capture those memories forever! Follow along with my photography endeavors at @jimmysonglove and good luck on that magical engagement!


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