Holiday Proposals: How to Make Them Special

The holiday season always seems to evoke love and happiness in equal measure, so it’s no surprise that this time of year is popular for those wanting to pop the question to their special someone. That said, many don’t necessarily realize that they can also be quite tricky to pull off in the midst of an already-hurried couple of months. Family and friends are planning their parties, their shopping, their dinners, and all the travel time in between. 

Yet, when properly executed, a holiday proposal can be incredibly sentimental and unforgettable. Take these tips into consideration as you prepare for making your engagement the most romantic it can be. 

Photography by David Abel

Going above and beyond 

The last thing you want is for your big gesture to get lost in the magic of the season. While it’s a perfect time to declare your love, it’s also important that you take the time to make the display feel unique. 

For example, Shannon Tarrant of suggests this regarding the setting: “Think through whether your partner would prefer a private moment or be asked in front of family and friends.” 

Alternately, Jen Avey with Destination Weddings Travel Group advises, “Jet off to paradise! Escaping the cold winter months and booking a trip to a warm, tropical oasis sets the stage for an extra-special holiday proposal. Destination proposals continue to be a popular option for those looking to really up the ante for a memorable experience.” 

Planning tips for your proposal 

Don’t allow the holiday distractions to interfere with your big plans for getting down on one knee. Pay close attention to what the moving parts will require, especially if you’re enlisting the help of hired vendors. This is a busy time of year for everyone, but most notably for those that are in the midst of pulling off winter weddings, such as a highly-coveted photographer. 

If you’re traveling or proposing away from home, Avey continues: “Always pack the ring in your carry-on rather than a checked bag – the last thing you want to deal with is a lost baggage scenario! When you get to the resort, put the ring box in your room safe where only you have access to the code. You don’t want your soon-to-be fiance(e) to find it by accident!” 

Kevin Dennis of Fantasy Sound Event Services says, “One of the best things about planning a proposal around the holidays is that your family and friends will likely already be in town, so you can organize a celebration fairly easy without drawing suspicion. Whether you choose to hold an impromptu engagement party or pop the question during a holiday get-together, you’ll be able to make the occasion even more special by having your loved ones involved.” 

Photography by Amy Kolo

Personalizing the experience 

As with any proposal, you want to ensure that your partner feels that the day is custom to who you are as a couple. It may take a few extra steps, but the attention to detail is what’s going to make the entire experience bespoke. 

According to Tarrant, “This could include the location of your first date, an activity you love to do together, or a special memory.” 

Dennis adds: “Consider making the post-proposal time an entire experience. Give yourselves a bit of private time together – whether it’s going to a special dinner afterwards, having cocktails at your favorite rooftop bar, or celebrating with champagne placed at the proposal locale. You’ll be grateful for this quiet time before you share the great news with all of your close family and friends, especially if you’re planning to take your partner to an engagement party right after!” 

Whatever you decide, take advantage of this beautiful time of year with the holidays as your backdrop. Plan carefully and incorporate meaningful details along the way! 

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.