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Tips For Proposing Around the Holiday Season

Tips For Proposing Around the Holiday Season

Published by Programme B

The holiday season is upon us and the festive warmth and love that everyone is surrounded by in this time of year are infectious. With family and friends all around, spirits high, and cosy feelings, there might be no better time to ask the person you love to marry you.

Making your proposal extra special is at the top of your priority list, of course. Things will already feel magical with the frosty Toronto weather, and the perfect ring from a trusted jeweller like Jonathan Goldberg and Kimberfire could be the cherry on the cake. With everything already in your favour, there is only one thing left – how will you ask?

We’ve rounded up a few creative Christmassy proposal ideas for you to consider.

Under the Tree

Since Christmas is a time of gift-giving, your partner might not be at all surprised to see a little box wrapped up just for them on Christmas morning. However, the surprise of finding you on one knee in front of them might blow them away (and probably be the best Christmas gift they’ve ever received). 


Christmas Cracker

For some people, the surprise of the proposal is the very best part. If your partner is the type to love surprises, catching them off guard with a very special Christmas cracker around the dinner table could be a great option.

You’ll need to use a DIY cracker, or make one yourself with the ring inside (preferably within a small box if there’s space). Include the classic cracker joke card but with a “Will You Marry Me” twist instead. Being surrounded by those you love most in the world will make this moment extra special.

Advent Calendar 

This is a super simple and special way to propose to your partner, and this option could be done in a more private setting if that’s what you prefer. Purchase an empty advent calendar (the kind that you can fill yourself) and fill each of the first 24 days with candy and little gifts.

The final box in the calendar, of course, will hold your engagement ring. You might want to leave it empty until just before, to avoid the surprise being ruined ahead of time!


In the Snow

Snow is the very best part of the Christmas season for some of us. If your partner loves the snow and being in the outdoors, you can use this to your advantage and make things extra romantic this year.

With a walk outside in the chilly winter air, a snowman holding a ring box, “Marry Me” written in the snow, you can really get creative in the ways you might incorporate the beautiful white winter into your proposal.


What’s more romantic than fireside cuddles, cosy blankets and hot cups of cocoa on late nights with the one you love? This might not seem like a grand gesture, but the intimacy of moments like these simply can’t be replaced. A romantic evening by the fire might be the perfect setting for your big question. 

Photo by Anastasia Belousova from Pexels