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The Dos and Don’ts of Holiday Proposals

As the holiday season comes to a close, many of us are probably noticing an uptick in engagement posts on social media. Some will be glossy looking carousels on Instagram, some will be quaint selfies in front of a Christmas tree—all indicate one unwavering trend: the holiday proposal.

Holiday proposals are great for a number of reasons. Typically, the family is all together, you may have already booked time off work, and the holiday season is, itself, full of joy for so many people.

But there’s still a short list of dos and don’ts to consider before you pop the question.

Understand Your Partner's Expectations

Here’s the truth: not everyone wants a holiday proposal. Some people may wish for a proposal on their own special day, with no holiday obligations or plans to detract from that special moment.

If you’re keen on a holiday proposal, make sure you have a great understanding of your partner’s expectations. At a minimum, you should know:

  • That your partner wants to get engaged

  • If your partner would prefer privacy or a party

  • If your partner is open to a proposal on a holiday

These are important questions to ask—either surreptitiously or outright—before you turn your holiday celebrations into an engagement party. It can be easy to get swept up in the magic of the holiday season, but don’t lose sight of what your partner actually wants.

Keep It Personal

Be it Christmas, Valentine’s Day, New Year’s Eve, or even Halloween, you’re probably considering a holiday proposal for a special reason. That day, and that holiday, is important to you.

But here’s where things can go wrong. Just because you want to propose on Christmas doesn’t mean you need to tumble out of the fireplace wearing a red Santa hat, ring box in hand.

Similarly, just because you love Halloween doesn’t mean you should propose dressed as Jack Skellington.

This is your proposal. So keep it personal! Make it about you and your partner, not the holiday. Unless your partner has always harboured a secret wish to accept a proposal while in a Halloween costume, find a way to make the holiday work in service of your proposal, not the other way around.

Take your partner for a lovely walk along a pathway lit with Christmas lights and propose at the view overlooking the harbour. Wait until the fireworks start going off on New Year’s Eve and steal away to pop the question.

When you propose, it’ll feel like the rest of the world has come to a standstill; so make that moment personal, intimate, and all about your love.

Consider Your Audience

Many people prefer to propose over the holiday season because they want to celebrate with family. After all, it can be difficult to get everyone together outside of bank holidays!

But there’s a balance to be struck. When you include other people in your proposal, you include their own feelings, opinions, and wants—which can quickly muddy the waters. You can also inadvertently exclude the folks that aren’t in attendance.

So consider your audience.

It’s a good idea to bring one or two trusted advisors (or co-conspirators!) in on your plan to run through potential problems. By asking your partner’s siblings, for example, if Great Aunt Millie will disown the family if she misses a public proposal, you can mitigate problems before they happen.

Letting one or two trusted family members in on your plan also ensures that it will run smoothly. They can help distract your partner, corral other family members, and make sure everyone is in the right place at the right time when you’re ready to get down on one knee.

Choose the Right Moment

What is the perfect moment for a proposal? How do you imagine it happening? How does your partner imagine it happening? Are you shouting the question to your partner as those NYE fireworks explode around you? Are you whispering it after Christmas dinner when everyone else has gone to sleep, but you’ve stayed up together? Are you proudly, confidently asking their hand in marriage in front of the tree while the family waits with bated breath?

The best way to figure out the perfect moment to propose is to run through the scenario in your mind.

Because here’s the thing: holidays are full of moments that are perfect unto themselves. When the ball finally drops; that first sip of coffee on Christmas morning before everyone is awake—you can have your pick.

So decide if you want to use a special holiday moment to propose, or if you want to create your own special “proposal moment” during the holidays. Both are great options—just make sure what you decide is right for the pair of you.

Take Time For Yourselves

A marriage proposal is always a reason to celebrate. It’s the biggest, hardest question you may ever ask in your life—as soon as your partner says “yes”, all of that stress and anxiety will melt away.

It’s normal to feel relief, happiness, and generally a little light-headed!

That’s why it’s important to take time for yourselves. Whether or not the entire family is in attendance, your proposal—and your marriage—is about you two alone. You deserve a glass of wine, a nice walk, or some other relaxing time away from the hustle and bustle.

The best way to ensure you’ll have time together is to plan it in advance.

Tell your co-conspirators that after the champagne has been polished off, you two will be having a wintry picnic to celebrate alone. Or you’ll be going out to a nice cocktail bar nearby. Or you’ll both simply be stealing away to have a quick nap after all of the excitement.

Your proposal, like your wedding day, will go by in the blink of an eye—especially during the holidays. So be sure to take a moment for yourself and to savour every passing second.

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