Tis the Season! 10 Romantic Holiday Proposal Ideas

Brianna Kozlarek / Thursday November 12, 2020

After the craziness of this year, we are EXTRA excited about the holiday season. At this point we’re taking any reason to celebrate, make things sparkly and focus on the love in our lives. There’s something extra special about a holiday proposal, so it’s no surprise that your timeline will probably start blowing up with announcements over the next few months. Things are a little (okay, a lot) scaled back this year, but there are still a lot of really creative & sweet holiday themed proposal ideas that we’re loving right now. None are too hard to do, but all of them are incredibly thoughtful (and photo-worthy). Check out 10 holiday proposal ideas below:

1.) Make the Most of Christmas Day

Kate Headley Photography | Classic Bride

“The holidays are filled with family, love, and tradition, such a magical time for a proposal! If you are thinking of proposing on Christmas day you may be wondering the best time to do this. Take your partner on an intimate walk after presents or before dinner. There will be so much magic in the air, your proposal will be private and a way to make for the most memorable Christmas ever. When you return home to your family there will be so much excitement to share and celebrate with those dearest to your hearts!” – Kaeleigh Testwuide, Founder of The Diamond Reserve

2.) A custom made advent calendar

Via Cuvus on Etsy

Make it yourself, or order one on Etsy that can be used as a tradition each year to come. Fill each date with special chocolates or tiny ornaments, pick the day you think best and sneak inside THE RING, maybe on Christmas Eve or even Christmas Day! This will be the most endearing surprise. Every year when you two use your advent calendar it will bring back the memories of the holiday season that meant your forever.” – Kaeleigh Testwuide, Founder of The Diamond Reserve

3.) Take advantage of the twinkling lights

Brooke Schultz Photography

Hire an amazing photographer. Typically, with holiday proposals, it is more than likely going to be in the evening time. Have to show off those gorgeous Christmas lights! With that, you want to make sure you hire a photographer who knows how to capture the moment in dim light. As amazing as our cell phones are, a professional photographer will do so much better at capturing and editing the moment.” – Krisy Thomas, Southern Sparkle Wedding Planning

4.) Incorporate your (or a new!) furry friend.

Sign via Tenmile Peak Shop on Etsy

One of the easiest things is to tie the ring around your pup’s neck with a ribbon (make sure ribbon isn’t too loose and dangles so your pup can chew the ring! Keep it collar-length.) You could also attach it to a cute sweater they’re wearing saying “marry me?” For the super trained pup — you can train them to pick up the ring box and carry it over to you!” – The Puppy Academy

5.) Plan a “Picnic with your Person!”

Nikki Santerre Photography |  Glamour and Grace

Jillian Rose Photography

To pop the question. The perfect way to celebrate, whether at the beach with a perfect sunset, a park, or your backyard. Talk About A Party created an experience to intimately and safely celebrate the occasion, and it includes decor, flowers, cheese & charcuterie, and water for 2.”

6.) Propose with her favorite color!

JoPhoto | Mountainside Bride

Propose with a fancy colored lab grown diamond. Colored diamonds are a way to make her ring stand out in a crowd, and choosing a center stone in her favorite color can add an extra personal touch to your custom engagement ring.” – Lindsay Reinsmith, Founder, Ada Diamonds

7.)Have a cozy night in

Via The Angelinos

…doing the things you love the most. Sometimes there’s nothing more romantic or unexpected than a quiet night in on a holiday when fancy dinners are expected. Have a comfy, cozy night in including takeout, some wine, a favorite movie, and just the two of you at home. One way to throw in a surprise and pop the question could be to opt for ordering some Chinese food takeout to complete your cozy, casual night in. Instead of using the fortune cookie from the restaurant, you could replace it with your own note that says “Marry me?!” for the ultimate surprise and plot twist to your date night in! There’s just something so romantic about the proposal taking place in your own home, with it being quiet as just the two of you share the special moment.” – Stephanie Allen, Allenbrooke Farms

8.) While Decorating the Tree


9.) A sweet breakfast in bed proposal.

Photographer: Sean Cook Weddings|Flowers: Bloominous|

Catch her off guard and start the day off with a surprise, rather than waiting until the evening to pop the question. It’s the perfect opportunity to treat them to a special meal you made yourself, brought to them in bed before they have to get up and get ready for the day (who doesn’t love to be woken up by the smell of freshly-baked French toast?!). Why not add a bouquet to the tray of breakfast, and last but not least, a hot cup of coffee that has a proposal engraved at the bottom of the mug, so once they’re done sipping they get surprised by a sweet note etched into their mug asking them to marry you!” – Stephanie Allen, Allenbrooke Farms

10.) Pop the question on the run – literally!

Casey Hendrickson Photography

If you and your better half are a fitness-loving couple, sign up for a holiday 10k! Not only will you get to spend lots of pre-race training time with your partner, but when you propose at the finish line you’ll both feel like winners. Invite friends and family to greet you at the finish line with signs that say “Congratulations!” or “He/She said YES!” It’s the perfect built-in excuse to have all your loved ones there to watch – and photograph! – the big moment. After you’ve stepped away from the other racers, take that ring out (of the zippered pocket or compartment where it was securely hidden), get down on one knee, and finally say those four, indelible words…it will surely be a moment the two of you will never forget!” – Jenna Miller, Creative Director at Here Comes the Guide

Couple: Amber Lynn Photography
Dessert Table: Amber Lynn Photography
Table Setting: Emilie Anne Photography via Ruffled Blog
Bouquet: Nadia D Photography via Project Wedding
Invitation: Rahel Menig Photography | Flower Girl: Hoffer Photography