Do’s and Don’ts of Proposing During the Holidays

by Alli

The holidays are around the corner, and you might be contemplating popping the big question to your significant other. Really? Proposing during the holidays? Maybe the idea of dropping on bended knee in front of the tree or under the mistletoe sounds like the sweetest most swoon-worthy proposal idea to commemorate a festive holiday engagement.

You would be wrong. Yes, yes, the mistletoe kiss and sweet ring presentation under the tree are cute ideas. But they have been done before. Many, many times. This is the biggest moment of your lives, not a pre-written holiday card trapped in a made-for-television holiday movie. Think bigger. Think better.

Proposing During the Holidays - Do's and Don'ts

Don’t fall for the obvious ideas when presenting the ring during the holiday season. Think outside the pretty ribbon-tied gift-wrapped box and plan an epic engagement that will be worthy of becoming a viral internet sensation.

Start planning now, because the clock is ticking. While no one can create the perfect proposal for you (that’s cheating!), there are a few ways to help inspire a bit of festive vision.  Let’s call these little tidbits the “Do’s and Don’ts” of holiday proposals.

Do…find out if the future betrothed likes public attention. This helps determine if the proposal should be quietly private and intimate or full-on crazy public.

Do…plan the date well in advance. Many couples have to bounce around between families during the holiday season and one or the other might need to travel out of town. Make arrangements accordingly.

Do…figure out which holiday to theme the engagement around. Each holiday offers unique ways to create a memorable engagement. Figure out if the engagement is going to be the gift of Christmas, Kwanzaa or Hanukkah, or if this will be the event that begins the New Year with a bang.

Do…set a budget. The ring is an expensive present. So set a budget for the engagement. An epic engagement doesn’t require a massive budget, it simply requires imagination. Regardless, don’t go overboard financially, so be sure to set a spending limit.

Do…capture the memories. Make sure you take photos!

Do…take a few hints. Some ideas have suffered from holiday overuse and have become cliché. Some have never been discovered. Here are a few holiday clues to get the vision focused…mix and match and make them your own:  skiing under the stars, a sleigh ride with blankets, Santa delivering presents (the ring is last), hidden in a gingerbread house, tie the ring to the hidden pickle ornament, propose at a midnight church service, frozen in ice, and Elves (get crazy with this one).

Proposing During the Holidays - Do's and Don'ts

Don’t…plan a stereotypical proposal. Spare the mistletoe. If you want to propose in front of family during the holiday, make sure the future fiancé is up for family involvement. Nothing is worse than the betrothed being caught off guard in the wrong way.

Don’t…bury the ring in a snowball. Yes, this might sound like a fun festive idea. But rings get lost easily. If you want to hide a ring, hide it in an object…or freeze it in clear ice so it’s visible.

Don’t…wait until the last minute to plan the proposal. No one really has nerves of steel during an engagement. The proposal makes even the toughest of men mushy, so please plan ahead. Last minute musings don’t always pan out well.

Don’t…tell the wrong friends. Some proposals require help. To integrate friends or family in a proposal idea, you have to feel absolutely confident that they won’t let something slip. Choose partners in the proposal properly.

The holidays are one of the most popular times for wedding proposals. According to The Knot, December is the most popular month to get engaged. Holiday proposals are magical and meaningful…just make sure you make the proposal your own. Whether the ring is presented during Christmas, Hanukkah, Kwanzaa or as the ball drops on New Year’s, a proposal during the holiday season ensures that the engagement will be filled with festive Brilliance.


Robin Masshole Mommy December 21, 2016 - 6:50 am

My husband proposed on Christmas Eve. I was totally not expecting it and he went over and above to plan it out perfectly.

Annemarie LeBlanc December 21, 2016 - 1:42 pm

All these tips would really make the engagement memorable. I love the idea of freezing the ring in ice. My sons are not ready to propose to their girlfriends yet, but I am saving these ideas for future use. (wink!)

Chrishelle Ebner December 21, 2016 - 2:03 pm

I love the ideal of the pickle ornament. We are German and the hidden pickle has been a holiday tradition for years. I will have to remember that for my daughter’s boyfriend in a few years.

Bella December 21, 2016 - 6:12 pm

Proposals around the holidays is so magical! I hope that all the right people see this post to ensure they do it right! haha

Mimi Green December 21, 2016 - 8:39 pm

Great tips, they take me back to my youth. I got engaged on Christmas Day when I was 18. It was cool, I was 18 and so yeah. He did it after we had opened gifts and I totally didn’t see it coming.

Jacqui @FlightsFancyMom December 21, 2016 - 8:41 pm

Good point about not becoming a cliche. Love the sleigh ride idea :). And lord NO! Definitely do not bury the ring in a snowball! Great post!

Stephanie of The TipToe Fairy December 21, 2016 - 9:20 pm

We got engaged on my birthday, so I guess it was a bit of a holiday for me. I do love the idea of hiding the ring on the pickle ornament. We have one of those and that would be super cute.

Pam December 21, 2016 - 9:47 pm

My now son-in-law proposed to my daughter in public on New Year’s Eve during th fireworks. They had discussed it in advance though.

Maureen @Scoops of Joy December 21, 2016 - 9:48 pm

This is awesome tips and I giggled at burying the ring in the snowball lol. My fiance actually proposed non-traditionally not with a ring too but with Nikon camera – on bended knee too. We are still shopping for an engagement ring 😉

ricci December 21, 2016 - 9:54 pm

I’m a single lady and have always said that I didn’t want to get engaged during the holidays. I want my engagement to be it’s own holiday! HA!

Jenn December 22, 2016 - 10:50 am

I am so glad my husband was not one that purposed on a holiday. In-fact we ended up getting married after discussing it, I don’t think he ever really purposed.

Gwendolyn Mulholland December 22, 2016 - 11:56 am

These are great tips for proposing during the holidays. It has been a long time since my hubby proposed and that was on my birthday. He did tell my family so he could plan it which was sweet.

Amanda @ Move Love Eat December 22, 2016 - 9:34 pm

Oh my goodness I can’t tell you how much I love this post! I’m not engaged, nor married however I would want it to happen any time other than a holiday/birthday etc!

Bonnie @wemake7 December 23, 2016 - 8:12 am

Great post. These are some really great tips for those that are contemplating this.

Rebekah Price December 23, 2016 - 8:40 am

Josh proposed to me on Christmas Eve. I was shocked and so happy. It made that Christmas! Obviously, it was a good idea. Here we are 14 years later, and we’ve given y’all 4 grandsons. I just still can’t believe he asked dad for my hand in marriage in the bathroom while they were washing their hands. ??

Terri Beavers December 23, 2016 - 5:25 pm

Awww what great tips. My daughter recently got engaged and she was overjoyed that he went out of his way to make it special. I’m going to send her the link to your post so she’ll have some ideas on how to plan the wedding.

Garf December 26, 2016 - 10:15 am

Great tips. My husband did not propose to me on Christmas Eve. He proposed from 10,000 miles away and over the phone (long story). It sounds crazy but we are still married and will be celebrating our 12th anniv soon.

Sandy December 26, 2016 - 12:19 pm

Amazing suggestions. I think I have to take some good tips from the article.


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