Holiday Proposal Ideas to Get Engaged by New Year’s Day!

Published Friday, Nov. 28th, 2025

10 creative holiday proposal ideas to get engaged by New Year’s! From cozy winter moments and festive surprises to romantic Hanukkah, Kwanzaa, and Christmas engagement ideas, make your engagement unforgettable this holiday season.

Stylized photo with holiday tree inside a ring box, symbolizing winter engagement ideas. — (Photo: Bozena Milosevic / iStock)

Dreaming of the perfect Christmas marriage proposal, or creative way to say 'Will You Marry Me?" during the holidays? Start here!

The holiday season is full of magic and the joy of new beginnings ahead. What better way to celebrate this special season than by asking the one you love most to marry you? Whether you’re dreaming of intimate moments, festive gatherings with friends and family, playful surprises, or unforgettable romantic gestures, these holiday engagement ideas are sure to make your proposal the highlight of the season.

Two men kiss and take a selfie in front of christmas trees

Tis the season for love! (Photo: RobertPetrovic / iStock)

1. Plan a Countdown Advent Calendar Proposal

Propose with a holiday advent calendar! This one will only work if you can keep a secret, but the anticipation will add to the romance: your sweetie will open a small gift each day during the countdown – opening the ring box on the last day.

2. Hide the Ring Inside a Christmas Cracker

Propose with a pop! Place the engagement ring box inside a decorative Christmas cracker for your partner to find, and watch as their eyes light up with surprise. Perfect for a Christmas marriage proposal with friends and family around, or a playful moment anytime this holiday season.

3. Candlelight Proposal on Winter Solstice

Dreaming of a cozy winter proposal? Ask them to marry you by candlelight on the Winter Solstice! Whether you’re tucked under a blanket together on the porch, curled up on the couch, or walking down a snowy path by lantern-light, this idea is sure to make them swoon.

Man on one knee proposes to woman by candlelight in the snow

(Photo: NazariyKarkhut/ iStock)

4. Pop the Question at a Christmas Tree Farm

The smell of pine trees, brisk winter air, rosy cheeks, and a romantic moment for two! Plan a Christmas tree farm proposal for a holiday memory that will warm your hearts for years to come.

5. Holiday Card Photoshoot Proposal

Proposing during your holiday card photoshoot is the perfect way to ensure you capture the exact moment they say YES on film (or file). If you book a professional photographer, let them in on the surprise so they can set up the perfect shot.

Plan ahead with these great tips: 10 Winter Engagement Photo Outfit Ideas & Advice

6. Romantic 8 Gifts Hanukkah Proposal

Getting engaged during Hanukkah? Say YES to these sweet idea. Give your partner a gift each day of Hanukkah: a romantic love note, chocolate gelt, a handmade scarf or trinket, anything they’ll love. On the eighth day, surprise them with the sweetest gift of all – an engagement ring!

Menorah and engagement ring box

Engaged for hanukkah: save your proposal for the eighth day, the sweetest gift of all. (Photo: Mizina / iStock)

7. Kwanzaa Proposal During a First Day Feast (Umoja)

The first day of Kwanzaa is all about unity, bringing family, friends, and community together. This makes it a natural choice for your marriage proposal! Ask your sweetheart to marry you over a delicious dish of your favorite food, surrounded by the people you cherish.

8. Mistletoe Proposal

Pop the question under a sprig of mistletoe for a romantic moment that’s sealed with a kiss. This idea is perfect for a private proposal at home, a family party, or a festive holiday event – anywhere there’s mistletoe!

9. Macaron Gift Box Proposal

Choose an assortment of your partner’s favorite French macarons from your local bakery and arrange them in a decorative gift box. Add a macaron shaped ring box or trinket with your engagement ring placed inside for a sweet surprise proposal any time during the winter holiday season!

10. Engagement Ring Ornament

If you and your sweetheart are decorating a Christmas tree or Hanukkah bush this year, add a special surprise between the cheerful strands of lights and seasonal bobbles – a ring box ornament! Place your engagement ring in a heart shaped ring box ornament and pop the question whenever the mood is right.

Christmas proposal, man on one knee proposing to girlfriend in front of christmas decorations

Sweet engagement idea for Christmas or Hanukkah? Hang an engagement ring ornament from your holiday tree, bush, or garland for your sweetheart to find. When it's time, pop the question! (Photo: martin-dm / iStock)

More Christmas Engagement & Winter Wedding Ideas

Jessica Levey

Lead Staff Writer & Illustrator

Jessica loves exploring the history and magic of ritual, the connections between people and places, and sharing true stories about love and commitment. She's an advocate for marriage equality, LGBTQ+ rights, and individuality, and is an ordained Minister with AMM. When she’s not writing or illustrating for AMM, she enjoys city hikes, fantasy novels, comics, and traveling.

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