Holiday engagement party invitations

Snow falling, holiday lights galore, families gathering together — it’s the perfect time of year to ask your significant other that big, special question! But what’s the best way to pull off a holiday engagement?

We’re here to help with all of our favorite holiday proposal ideas. There’s a reason the holiday season is one of the most popular times to pop the question. Discover how you can plan a wonderful, personalized proposal moment with these tips, location ideas, and creative holiday engagement ideas.

12 Holiday Proposal Ideas to Help You Plan the Perfect Festive Engagement

Holiday engagement: man proposing to a woman

With so much love and joy in the air, it’s no wonder that holiday proposals are so popular. If you’re planning to pop the question this season, enjoy some of our favorite holiday and Christmas proposal ideas — from picking out the perfect ring to creating a dreamy festive scene.

1. Think About What Your Partner Would Love

Holiday engagement: Corner Confetti Announcement

Design: Stacey Meacham Design, LLC (photo courtesy of Angela & Evan Photography)

Matching announcement: Corner Confetti Announcement

Before you dive into brainstorming holiday engagement ideas, consider what your significant other would love the most. You know them best, and this is a big moment for you both, so plan with that in mind.

Would they say yes if you plan a surprise proposal in public, or would they prefer a more quiet, intimate moment? Would they love you to recreate your first date, or plan an exciting, completely new adventure instead? Is a public proposal perfect, or is a proposal at home more their style?

2. Take Inspiration From a Movie

Do the two of you have a favorite Christmas movie? Is there a holiday classic that your beloved watches every year? If either of these are true, why not base your proposal location, activity, or words on that film?

Whether you pop the big question in New York City under twinkling lights, get down on one knee in the park, or ask the question when you’re snuggled up at home, using a scene from a movie as inspiration for holiday engagement ideas is a wonderful way to make it feel special and personal.

3. Choose an Engagement Ring That Suits Their Taste and Personality

For every aspect of a marriage proposal, personalization is key. It’s something that’s especially important when it comes to buying an engagement ring (and later on, the wedding ring) as your significant other will wear it every day.

Choose an engagement ring that matches your partner’s style and preferences. If you can, talk about preferences before you get engaged — that way you can be sure you’ve chosen a style, metal, and gemstone that they will adore. If you want to keep the whole thing a surprise, gather insights from the types of jewelry they already wear, their favorite colors, and anything they’ve hinted at previously.

4. Prepare a Personal Message

Holiday engagement: Fun Snapshot Announcement

Design: Jessica Williams (photo courtesy of Carina Skrobecki)

Matching announcement: Fun Snapshot Announcement

Many people like to prepare a personal message in advance so they have a way to remember all the beautiful words they want to say in the moment. If that’s you, start thinking about how you want the moment to feel and how you can create that atmosphere with words.

Don’t feel like you have to plan an epic monologue for your holiday engagement, though. Recounting a memory you love and ending with “will you marry me?” is just as romantic as sharing your entire love story from start to finish.

5. Choose the Right Moment

It’s a busy time of year, and there’s probably already activities, events, and celebrations in your calendar for the holiday season. Keep this in mind as you look for the perfect time to pop the question to your loved one.

Think about whether you want a festive proposal on Christmas Eve or Christmas Day, or whether you want to step into the new year as a freshly engaged couple by proposing on New Year’s Eve. Make your timing feel special, too. Will you propose over breakfast on Christmas morning, or while you’re enjoying a day out at a local festive market?

6. Hire Christmas Carolers

Choir holding some notebooks while singing

For a fun and festive way to ask your loved one to marry you, invite some carol singers along for a one-of-a-kind performance. Ask them to come to your door or your holiday party to sing traditional holiday songs, then end the performance with your proposal. Or better yet, gather some of your loved ones to sing carols and witness the special moment.

This is a sweet idea if your partner adores carol singing and wants to get into the seasonal spirit. You could even get involved with the singing as an extra surprise for your spouse-to-be.

7. Say It With an Ornament

Surprise your loved one with an extra special Christmas ornament for the tree this year. Hide the ring inside an ornament or decoration, and hang it somewhere that’s out of sight, then ask them to find it.

This holiday proposal idea works if you want to propose while decorating the tree together, or if you want to save the moment for later on in the season. If you choose the second option, make sure you hide the ornament well or have it blend in with your existing decorations!

8. Get Others Involved

Twilight Sparkle Invitation

Design: Snow and Ivy

Matching engagement party invite: Twilight Sparkle Invitation

If your partner is open to the idea of a surprise or public holiday engagement proposal, getting their friends and family members involved is a touching way to make that moment feel even more touching.

Turn a planned holiday event into a surprise proposal, or get their loved ones to help you create a video slideshow of your favorite moments together — they’ll love getting to be part of your holiday engagement ideas. Not only can their family members and friends offer valuable support for the proposal, but their ideas and memories can help you with wedding planning too.

9. Choose a Festive Scene

One of the best holiday engagement ideas is to use the festive magic that’s all around you. There’s so much happening at this time of the year that you can take advantage of all those winter wonderland events and scenes as the ideal setting for your proposal.

Visit the ice skating rink, take a road trip to look at the best Christmas lights, or book a sleigh ride while you sip on hot chocolate. Visit the Christmas tree farm to pick out this year’s tree, walk through a festive market to buy gifts, or hang up some fairy lights and mistletoe at home to create your own cozy festive moment. It’s like a rom-com in real life!

10. Propose Over Holiday Dinner

Man proposing to his girlfriend

If you’re planning a romantic Christmas dinner for just the two of you, why not turn that into the ideal holiday proposal? You’re already putting a lot of energy and thought into preparing a delicious meal and a beautiful tablescape, which can create a lovely backdrop for your holiday engagement proposal.

Sit down together to enjoy your meal, then reveal the ring after you’ve finished dining. Hand over a beautiful ring box as you ask the question, or make a toast and ask how they’d feel about becoming your lifelong partner. 

11. Give the Ring as a Gift

The holiday and Christmas season gives you lots of fun ways to surprise your loved one with a gorgeous ring. Hide the ring as a gift and watch the look in their eyes as they unwrap it and realize what’s happening.

Feature the ring as the last surprise in a homemade advent calendar, or wrap a ring box in something comically large so they have no idea what’s inside. Write a Christmas card or holiday card that hints that Santa has brought a special gift this year, or keep it a complete surprise until the moment they unwrap it.

12. Book a Photographer

Omg Yay! Announcement

Design: Paper Raven Co.

Matching announcement: Omg Yay! Announcement

Whatever holiday engagement ideas you come up with, it’s a moment that you’ll both remember forever. Having some visual reminders can make it feel even more treasured and remind you of your holiday proposal for years to come. Consider whether you’d like someone to capture some photos or videos of either the proposal or your celebrations afterward.

Book a photographer to document the moment from a distance, or set up a camera to take a video of your holiday proposal. You could also book a wedding proposal photoshoot where the two of you pose for social media candids or more formal images to share with your loved ones when you send an engagement announcement. This is a busy time of the year for photographers though, so secure your time with them soon!

Seal the Deal with a Thoughtful Holiday Engagement Idea

The best holiday engagement ideas come from the heart, feel personal, and celebrate your love story. Use these marriage proposal ideas to help you put together a foolproof proposal plan and come up with a fun, special way to make the moment magical.

Keep that special moment feeling a little longer by sending announcements to your loved ones. Browse our engagement announcements and select your favorite to share your exciting news far and wide, with customizable designs that let you create something as beautifully distinctive as your love story.