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Five Holiday Proposal Ideas to Inspire You

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Christmas is coming. And if you’re in a long-term relationship that feels ready for the next level, perhaps you’re thinking about popping that question. If that’s you — if you’re ready to ask your significant other whether they’d be down to get hitched — we have some creative, holiday-themed proposal ideas that could set you up for a truly unforgettable moment. 

Let’s get those creative juices flowing and settle on a fun and romantic way to pop the big question. And after you lock down that Yes!, you can start thinking about a gift for yourself, hooking it up with the freshest men’s wedding bands this sweet world of ours has ever known.  

Pop the Question with Lights and a Drone

If you’re looking to propose around Christmas and have been wracking that creative mind of yours for the most fabulous ways to go about it, there’s about a 95 percent chance you’ve mulled the possibility of proposing with a holiday light show. 

That’s most definitely a fine idea. Have her flip a switch and there’s “Will you marry me?” written out in string lights. But what if you add some spice to that plan and take things aerial? 

We’re talking crafting that string light message in your yard, on your roof, in a big-ass wide open field — any place where it requires a little perspective to get the message. It could play out like this: You give your guy or gal an early Christmas gift — Oh look, a drone! You take it out in that cool night air for a test spin. And once it’s up there high enough, the message written on your roof comes into view in the video screen affixed to the drone controller. 

She’s gonna say Yes! And when she does, pop that top off your flask and warm up with a little nip of hot toddy you’ve crafted for the occasion. 

Now that’s a good proposal.

Turn a Dreaded Wintertime Task into Something Unforgettable

Perhaps this one’s a little cheesy. And it certainly only works for those in predictably snowy/icy winter climes, though we hope the idea inspires a creative spark in warm-weather dwellers, too.  

For those cold-weather peeps, doesn’t deicing/scraping windows rank at the very top of annoying winter tasks? Well, what if that terrible act leads to a big reveal: a hidden message underneath? A little “Will you marry me?” written in shoe polish. You can spread the message out over multiple windows, adding an extra layer of drama to the reveal. Click here for a quick tutorial on car-window writing. 

You should try a test run here to make sure your method works. And you definitely want to avoid this on days when your spouse-to-be (fingers crossed) actually needs to get somewhere in a damn hurry. Mess with some urgent plans and you’re unlikely to have a proposal to remember (at least not in a good way). 

Pop the Question with a Santa Style Note

You know those cute little notes kids leave out alongside a plate of cookies and milk for Santa to find? Well, why not whip out the crayons and craft a little proposal? You can go ahead and stick with the cookies, but instead of milk, break out the champagne. 

Unbox It

You know how unboxing videos are kind of all the rage these days? Why these videos get millions upon millions of views on YouTube is something of a mystery, but it likely comes down to anticipation — waiting to see what’s in there, getting a peek, waiting for the next peek.  

Well, consider popping your question with notes wrapped up in a series of boxes. You can play this any number of ways, but consider this sequence of romantic events: The bow comes off the first box and the lid is lifted to reveal a note: I have a question… The next box gets opened: …I’ve been meaning to ask you. The next one: Will you… And then the final box opens to reveal Marry me? written on a sheet that rests alongside that to-die-for engagement ring you’ve picked out. 

Take a Knee and Say It from the Heart

These days, we often think in terms of what’s most Instagrammable. What’s gonna light up the Gram and get hundreds of likes and comments. But maybe you need to scrub that social-media influenced approach from your mind and kick it with an old-school proposal. Hear us out: Maybe it’s Christmas Eve. You’re home. Maybe a fire’s going. Christmas lights and candles are twinkling. You’re having a little drink. The atmosphere couldn’t be cozier. 

You take a knee, profess your love, say how blessed you feel to have found each other. And then you ask her to marry you. 

Perhaps that simple idea is the very best of all.

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Christopher Stern
Christopher Stern is a Washington-based reporter. Chris spent many years covering tech policy as a business reporter for renowned publications. He has extensive experience covering Congress, the Federal Communications Commission, the Federal Trade Commission, and other federal agencies. He is a graduate of Middlebury College. Email:[email protected]

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