Planning the Perfect Holiday Proposal: 5 Pro Tips for Getting Engaged During the Holidays

With dreamy twinkle lights, cozy sweater-weather, and endless love in the air—there’s really no more magical time for a proposal than the holidays. But, with family often in town and tons of celebrations to attend, pulling off a holiday proposal can take more planning and forethought than you might think. Today, then, we’re offering up our top five pro tips for the dreamiest, planned-to-perfection holiday proposal.

Photo By Lauren Michelle Photography / Read Stephanie and Dan’s Full Story Here

5 tips for getting engaged during the holiday season

1. Make sure your future fiancé wants an audience.

Before you pop the question on Christmas morning in front of your extended family or at a New Year’s party with a crowd gathered around, make sure you’re confident that’s what your partner actually wants. While public proposals are popular as ever, not everyone wants to get engaged in front of friends and family. You can ask some questions on the sly or talk to your partner’s close friends ahead of time to see if a public proposal is a good idea.

Also, consider the crowd: if your fiancé-to-be is introverted but really values her close relationships, she might be thrilled with a proposal in front of her closest friends and family, but not so thrilled about it happening in front of strangers. If he or she is outgoing and loves being the center of attention, on the other hand, they might love the idea of being proposed to in front of a large crowd (think: at a New Year’s Eve party).

2. Make sure the moment is yours…and only yours.

Holiday proposals are popular (as in, super popular). Make sure no one else in your family is thinking of popping the question on the same night as you are. The same goes for friends at a New Year’s Eve party. You don’t want to plan the perfect proposal and have a ring waiting in your pocket only to be beaten to the punch by another party-goer.

3. Time it right.

Holiday celebrations are busy…and loud. Make sure you have a window of time where your partner will actually hear you ask the question (right at midnight on NYE may sound romantic, but it often poses logistical issues and can make for a proposal she doesn’t hear). From toasts to meals to family traditions, think through everything that will be happening at the party or gathering—and then decide what moment will be the most magical, memorable, and practical for your holiday proposal.

4. Don’t do it alone.

If you’re proposing in front of others, make sure you have some help with the magic moment from those in attendance. You don’t have to let everyone know (especially if you want the moment to be a surprise for most of your family or friends)—but you should have at least 1-2 people who you trust who can help coordinate things. Taking everything on yourself may seem do-able, but chances are you’ll be anxious and likely pretty distracted when the moment arrives. Having someone else who knows to cue the lights, turn down the music, have a camera ready, etc. will ensure your engagement goes off without a hitch.

Enlisting the help of others also means turning to online tools and resources as you plan the perfect moment. Some of our favorite pieces on holiday proposals include:


5. Don’t limit yourself.

A holiday proposal doesn’t always have to be on Christmas or New Year’s Eve. Simple, sweet moments in between the big days can make for the perfect time to propose without the added complications that often come with Christmas Day or New Year’s Eve. Remember—while public holiday proposals involve lots of other people, they’re really only about the two of you. If a Christmas morning proposal in front of your family of 30 doesn’t feel right, opt for something more intimate or creative instead. A picnic under your Christmas tree, a celebratory brunch, a snowy hike, or an evening spent walking around town looking at Christmas lights are all great options for an off-the-beaten-path, intimate holiday proposal.

Photo By Alan Tran / Read Kenzie and Charlie’s Full Story Here

Ready for some inspiration before you pop the all-important question this holiday season? Check out our favorite holiday proposals here.