How to Pull Off a Surprise Proposal During the Holidays

If you’re like us, you might be a little tired of all of the curveballs 2020 has thrown at us. Admittedly, this was a year that really tested our patience, perseverance, and our ability to surf the highs and lows – and there were a lot of lows. But now that we’re beginning to see the light at the end of the tunnel, it’s the best time to end the year on a good note. 

The holidays are quickly approaching, and for many, that means planning a proposal for your partner. So, if you’re looking to pop the question, you might be thinking – how can I make this experience unbelievably special and keep it a surprise? 

Have no fear, our wedding industry experts gathered all of the most coveted tips and tricks to help you navigate a holiday engagement. 

Why the holidays are an ideal time for proposing 

When it came to the idea of proposing in years’ past, the holiday season seemed a bit too predictable or even cliché for some couples. However, in recent years, we’ve seeing a rebirth of love for these engagement experiences.  

Jamie Chang of Mango Muse Events notes, “The holidays are an especially popular time for engagements because it's inherently a happy and special time. The holidays are about spending time with family and being appreciative for everything you have. So, when you're thinking about proposing, it's the perfect time because all those feelings and holiday spirit just add to the heightened feeling of joy of an engagement. But another reason is because the holidays come at the end and beginning of the year, which makes an engagement an exciting way to end and/or start a new year and a new journey.” 

Faith Folayan of This Love Weddings adds: “Holidays are especially popular for engagements because it's a seamless way to gather loved ones together while your significant other is none the wiser. Also, for those that may not have the best holiday memories it's a way to establish a new tradition and special memories for years to come. The holidays are such a romantic and memorable time of the year!” 

Tips for keeping it a surprise (even if you’re bad at keeping secrets) 

It’s difficult enough to keep a proposal a surprise at any time of year, but with the excitement of being surrounded by family and friends, the pressure is on to keep it under wraps.  

Juls Sharpley of Bubbles & Bowties advises: “You do actually have to PLAN to propose. I know it seems crazy, because you want it to be/seem spontaneous, but you also want to get it right. If you're having someone capture it in any capacity, even if it's a friend with their phone, go to the place where you want to propose (ideally at the time of day you want to propose) and make sure you'll know where they'll be hiding or standing, and where you want yourself positioned for the proposal! And then, why not have a little treat to celebrate with after, whether a bottle of champagne or chocolate covered strawberries!” 

According to Jen Avey of Destination Weddings Travel Group, recruiting help is the key. “Whether it be a close friend or a professional event planner, we recommend enlisting the help of at least one or two allies to help pull off the perfect surprise proposal. They should take some (if not, most) of the stress off of you by taking care of the details, running errands, securing any vendors, etc. so that all you have the think about is your speech (and not losing the ring)!” 

Image by Amy Kolo

Things to be mindful of when planning your engagement 

There are a few additional things to keep in mind, especially when it comes to including family and friends, as well as coordinating logistics. 

JoAnn Gregoli of Elegant Occasions by JoAnn Gregoli says, “When pulling off the ultimate proposal, you have a few options. You can hire a planner who will execute the surprise flawlessly, or enlist the help of your family and friends. Also, you must hire a photographer and videographer to capture the occasion. Plan out the proposal in advance, and don't wait until the last minute to make the arrangements. Details do count!”  

And lastly, “Be sure to take advantage of the Black Friday and holiday promotions when it’s time to ring-shop,” suggests Folayan. 

In a time of uncertainty, a holiday proposal is within your control, and you hold all of the cards when it comes to giving your partner a gift that they deserve. Don’t be afraid to pull out all of the stops – just be careful not to ruin the surprise! 

Meghan Ely is the owner of wedding PR and wedding marketing firm OFD Consulting. Ely is a sought-after speaker, adjunct professor in the field of public relations, and a self-professed royal wedding enthusiast. 

We've partnered with OFD Consulting to bring you this great advice from their collective of wedding professionals.