8 Mistakes to Avoid If You're Proposing During the Holidays

The holiday season is right around the corner, and while this time of year is meant for spending time with family, participating in traditions, and enjoying the festivities, it’s also engagement season. Whether it’s due to being surrounded by loved ones or the magic associated with these cold-weather months, many people plan to pop the question during November or December. If you count yourself among them, you may already have the perfect proposal planned out. Maybe you’re considering asking the question at your family’s annual holiday party or when you pick your partner up from the airport. However, before you head out to pick up the ring and begin plotting out the moment, there are some common mistakes surrounding a holiday engagement to consider. 

“While the holiday season seems like the perfect backdrop for a romantic proposal, there are some deeper considerations that often go overlooked,” says Love McPherson, a certified marriage and family counselor and relationship expert. Being aware of these common blunders can help ensure your holiday engagement goes exactly as planned. Ready to pop the question? Before you drop to one knee, read on to avoid making these common mistakes during your holiday engagement.

Not Considering Stress Levels

“The holiday season is already loaded with emotions, expectations, and traditions,” McPherson says. “Forty percent of people report experiencing increased stress levels during the holiday season. Women tend to report higher levels of holiday stress compared to men.” As a result, consider how a holiday engagement will factor into your partner’s mental health. For example, if they’re tasked with hosting Thanksgiving, popping the question on their busy day may not be the best idea. Find a moment when they're feeling at ease—and can bask in the excitement of the proposal. 

Not Personalizing Your Proposal

It’s a familiar sight: When you scroll through your social media feeds in November or December, you may see more than a few posts accompanied by a caption announcing a couple’s holiday engagement, McPherson says. To avoid becoming one of the many, make sure your moment feels personal and intentional—rather than it occurring just because “everyone else gets engaged this time of year,” she adds. Be sure to plan a proposal that is meaningful and speaks to your relationship; pick the place where you had your first date or work in a reference to a shared passion when you ask for your partner’s hand, she adds. These small details can make the moment feel intentional and personal.

Not Choosing the Right Moment

Picking the right time to propose is one of the most important aspects of any holiday engagement. “Proposing during someone else’s celebration—like a holiday party—can be a major faux pas, as it may unintentionally shift the focus from the festivities to your personal moment,” says Lisa Mirza Grotts, an etiquette consultant and the author of A Traveler’s Passport to Etiquette. Instead, consider popping the question during a more private moment. “An intimate dinner for two can create the perfect atmosphere for your proposal. Afterward, you can share the joyous news at a gathering, allowing everyone to celebrate together,” she suggests. 

Not Respecting How Others Feel During the Season

Unfortunately, not everyone has positive memories associated with the holiday season. “For many people, the holidays are a time filled with joy, but for others, they can also be marked by loss or personal tragedy,” McPherson says. “High emotions, lingering sadness, or even feelings of guilt about celebrating can surface, which might make it difficult for your partner to fully enjoy the moment.” If there’s a particular day or event that evokes a lot of emotion in your partner, avoid popping the question on or around it.

Ignoring Your Family’s Perspective 

For many, family is a large part of this season. And while involving your loved ones in your holiday engagement may be a goal of yours, make sure you’re not stepping on anyone’s toes by asking for your partner's hand at the wrong time. “If your family has a strong attachment to holiday traditions, but [aren't particularly close to] your mate, proposing during this time could feel like an intrusion, creating unnecessary tension,” McPherson says. “This could leave your partner feeling torn between celebrating her joy with you and navigating family disapproval.” 

Not Thinking of the Finances

Between gifts and travel expenses, costs associated with the holiday season can quickly add up. Before popping the question, McPherson recommends ensuring you have enough money saved up to plan the proposal—and the subsequent celebration—you’re envisioning. “Will you be able to invest in the kind of ring or celebration that reflects your intentions, or will seasonal demands force compromises?” she says. “Thoughtfully navigating these factors ensures your proposal enhances, rather than complicates, the season for both of you.”

Not Considering Your Partner’s Personality

Not everyone wants a public proposal. Before dropping to one knee at a large gathering, make sure you’ve considered what your partner may want in a holiday engagement. “Keep your partner's preferences in mind. For those who value privacy, a proposal in front of a crowd might feel overwhelming,” Grotts says. “Tailor your approach to what feels right for both of you.” McPherson agrees. “If your partner prefers private moments over public displays, this could feel overwhelming rather than joyous,” she says. “On the other hand, if your partner is [more outgoing], you may want to bring in the crowd to create the vibe that adds to her joy.”

Not Thinking of the Future 

Once you tie the knot, your wedding anniversary will likely become the most significant date in you and your partner’s relationship. However, the date of your holiday engagement can be just as important. “Holidays come around every year,” McPherson says. “Does your partner want the engagement anniversary and holiday memories to overlap forever? For some people, that’s beautiful. For others, it might take away from the uniqueness of the moment. Be sure to honor their personality and preferences.” 

Ultimately, there’s no one-size-fits-all approach when it comes to popping the question during the winter months. “The perfect proposal is one that makes your partner feel seen, known, and cherished,” McPherson says. “It's not about grand gestures or viral-worthy moments for some—yet it is for others. But for everyone, it’s about a personal moment that speaks directly to the heart of your relationship.”