Should I Propose on a Holiday?

by in — Updated January 24, 2023

You’ve found the one you want to propose to. Awesome! That’s step one. Step two, which is equally tricky and terrifying, is when to propose.

Have you ever uttered the words “ugh, that’s so cute I want to die” at any point during a holiday movie? If so, you might be a prime candidate for holiday proposals (on the proposing or receiving end, honestly)! Yes, we realize that sounds like a marriage version of a Jeff Foxworthy bit (deep cut there, for sure), but seriously.

If you don’t want to read any further, here’s the real quick version: If you’re proposing with a classic, tried and true ring, you might be fine proposing on a holiday. If you’re more of a fan of unique wedding rings, maybe hold off. Yes, that was both quick and unscientific, but it’s not a half-bad litmus test. If you’re still scratching your head, fear not.

Is Your Partner into It?

Painfully obvious questions deserve first billing in my book. Seriously though, this is really the only question that matters.

Is your partner someone who would appreciate a holiday proposal? Is Christmas a family affair in that household? Does Grandma Ethyl come out of the woodwork to make her annual appearance when Saint Nick heads to town? If so, by all means, propose away, young buck.

Does your partner reel at the sight of a rom-com? Does your partner find Ryan Gosling repulsive? If so, first of all, woefully mistaken. Seriously, it’s like he’s photoshopped. Not jealous, just observing. If cliché is horrifying and not endearing, you probably already have your answer.

Should I Propose on a Holiday? 1
Source: Simplylove/

How to Propose Around the Holidays

Look, if you’ve made it this far, clearly you think your partner will dig a holiday proposal. Maybe you just like hanging out and reading about proposals – we don’t know your life. The point is, if you want to make this Christmas/New Year’s/Flag Day special, you gotta know the ground rules.

Rule 1: Make It Special

Cliché can be endearing to the right person. However, lean too far into the cliché, and you seem unoriginal and not entirely in the moment. That’s not you. You’re jumping in with both feet, and we love you for it. Let’s make sure you don’t come off that way accidentally.

Should I Propose on a Holiday? 3
Source: Syda Productions

Unless The Proposal is a staple of your relationship (or you’re dating Sandra Bullock), don’t recreate a scene from it. As a rule, don’t recreate anything unless it’s a serious touchpoint in your relationship and holds some of your best memories. You want it to come from the heart and be fully honest. The further you get into a bit, the further from sincerity you seem.

Rule 2: Make It Private

Now, let’s be clear. Your partner wants friends and family around for the proposal? No doubt, bring the whole gang. However, make sure you make some time for just the two of you at some point in the very near future post-proposal.

If your partner isn’t a big fan of the grand gesture with everyone watching, maybe find a loose aunt (there’s always one running around at family gatherings, or so we hear) and have her discreetly film the proposal. Even the most private person will appreciate the ability to relive the moment. Try to find the unoccupied aunt with the best videography skills, if possible. A loose uncle will do in a pinch.

Should I Propose on a Holiday? 5
Source: 4 PM production/

Rule 3: Consider the Day

Will you marry me? Yes? Alright, time to go to sleep. Not the sexiest proposal story (though potentially not the worst). Seriously, you have a whole day. You probably have a sweet set of activities planned before the proposal, but what about afterward? If you haven’t had any time for just the two of you, make sure you have something planned for after the proposal. A nice walk or maybe a romantic candlelit dinner.

Do what makes sense, but make sure you do something. It doesn’t matter how much you love each other, you just can’t stare into each other’s eyes for the next 10 hours without moving or doing anything.

Rule 4: Be Flexible

Look, the grand romantic gesture is an all-time movie bit. It works, and it will never die. However, everything goes wrong bit is an all-time romantic comedy bit, so prepare for that one just in case. It’s not about the minutiae of the proposal when you get to the core. You can’t plan out everything (especially Anna Faris crashing into your yard) and trying to do so is going to give you an aneurism.

You’ll already be a ball of nerves, so make a backup plan (or three) so you have contingencies if the unexpected comes up.

That’s it. That’s all you need to know. Should you propose on a holiday? Sure, if you love the classic, romantic aesthetic. A whole lot of people do. That being said, the holidays have so much pressure already. If you aren’t set on proposing on a holiday, it might be better to wait. You won’t be able to use the same present for Christmas and your anniversary, but maybe that’s a trade you’re willing to make.


Leave a Comment