The 10 Cutest Holiday Proposals (that we had to tell you about)

The holiday season is also known as “engagement season.”  With so many festivities and so much magic in the air, we get a little caught up in the spirit of things. From autumn strolls to winter weekends away, there are endless possibilities for a magical proposal. Here are some of our favorite holiday proposals. Enjoy!


Welcoming Fall: 

Fall is here and that means warm apple cider, football, and time to bring out those flannels! What better time of year to snuggle close to your loved one and kick off engagement season.

1. Autumn Strolls: The changing colors of the leaves make for breathtaking photo opportunities. Embrace the warm fall colors on a walk through the park, complete with a picnic and champagne, or maybe a hike in the mountains. Check out this couple who made the most of autumn’s natural beauty!

2. Pumpkin Proposal: What couple can resist searching for the perfect pumpkin together? Try presenting your choice pumpkin to her with the ring around its stem or maybe carving a sweet message for her to read. Brittany and Nick’s engagement is almost too cute for words. Complete with all the makings of fall; pumpkins, flannels, and a view!

3. Give Thanks: Thanksgiving is the perfect time to get everyone together and what’s more special than including close friends and family in your proposal! Check out this police officer who proposed in front of all of New York City (with the world watching).

A Holiday Proposal: 

Christmas is truly the most wonderful time of the year, especially for proposals! A holiday engagement is the perfect way celebrate the season.

4. Picking out the tree: A trip to the Christmas tree farm can be transformed into the most magical engagement. This festive proposal provides wonderful photo opportunities and a great way for you and your future fiancé to have a little fun with picking out a tree. Shereen was blown away by Josh’s intimate proposal complete with an already decorated tree! (Which will be cherished for years to come thanks to the help of a hidden photographer!)

5. Decorating for Christmas: Make plans to decorate the tree, put on some Christmas music, and then hide the ring for her to find. Try hanging it on a branch or ornament, or in her stocking!

6. Christmas Photo Surprise: This creative engagement surprise included friends, family, music and a ukulele. Plus, a hidden video camera captured the magic moment. This is MUST WATCH.

7. Puppy Proposal: We are obsessed with this growing engagement trend; I mean come on it’s a girls dream! Puppy – Check. Sparkly Ring – Check. New Fiancé – CHECK! This is the ultimate Christmas morning surprise.

Wintery Wonderland: 

There is no need to wait for a holiday to propose in the winter. Create your own special day in spectacular snowy setting.

8. Snowy Scene: On the city streets or away in the country side, snow can create the most magical setting for a winter proposal (just be sure to have some hot cocoa waiting inside).

9. Ski Trip: For the adventurous couple a weekend trip to a mountain lodge is a dream come true. As far as winter proposals, you can’t beat popping the question on top of a mountain! Or maybe after a long day on the slopes cozying up fireside for a proposal that’s sure to be romantic!

10. Sleigh Ride Surprise: Turn a winter weekend away into the memory of a lifetime. Plan a snowy sleigh ride and stop for a moment to “take a picture” aka, pop the question!

If you’ve got your own gears turning and you are looking for your partner to propose, check out this handy guide to getting him to propose on “The Knot.”

Tell us, which proposal is your favorite? Also, if you have a great story, please share in the comments below!

By: Dana Bates

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