Why Special Occasion Proposals Might Not Be the Best Idea

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Countless couples take advantage of major holidays and special occasions to pop the big question every year. Valentine’s Day, Christmas, New Year’s Eve, and even birthdays have become prime time for engagements, with many believing that tying a proposal to a memorable date adds extra romance to the day. 

But is linking a life-changing moment to a holiday always the best idea? While it can make for a cinematic and sentimental experience, it also brings emotional and societal pressures that might overshadow the moment’s authenticity.

Chris Bajda, a wedding expert and the founder of GroomsDay, weighs in: “A proposal should be about the couple and their journey, not just the spectacle of the day. While holiday proposals can be fun, they can also carry extra pressure—both for the one proposing and the one answering.”

Insights into why proposals can turn sour and why, sometimes, they work perfectly. 
Pressure to Say Yes 

When a proposal happens in a high-stakes setting like Christmas morning with family gathered or in the middle of a Valentine’s Day dinner in a busy restaurant, there’s an added pressure to say yes. With all eyes on you and your partner, the goal of having an intimate moment can turn into a stressful situation with the pressure to say ‘yes’. Remember that your goal is not to please a crowd, but to ask to spend the rest of your life with someone, so choose your venue wisely.

Festivities Overshadow the Proposal 

Holidays are already filled with traditions, emotions, and oftentimes stress. A proposal can either get lost in the shuffle or add another layer of intensity to an already busy day. If you or your partner are part of a big family and you are choosing to spend the holidays together, you should be prepared to have to compete with intense family activities and complex family dynamics. You may want to postpone the proposal if the holidays are shaping up to be chaotic.

It Might Not Feel Personal Enough 

While Valentine’s Day or Christmas proposals may seem romantic, they don’t necessarily reflect the couple’s unique journey unless they met on one of those days or have an important relationship milestone tied to a holiday. A proposal on a random Tuesday at a sentimental location might be far more meaningful than choosing February 14th or December 25th simply because they’re holidays.

The Big Day Should Be Yours 

Proposing at someone else’s wedding or a big family holiday event can unintentionally steal the spotlight from others. Couples who get engaged at weddings might do it because it’s a romantic setting and it feels right in the moment, but making a spontaneous decision like that could be received poorly. 

A wedding day is one of the most important days in a person’s life, so choosing to make someone else’s wedding about yourself can create tension or even cause resentment from the friend or family member whose wedding you are attending.

The Flip Side: When Holiday Proposals Work

For some couples, special occasion proposals make perfect sense. If a couple shares a deep connection to a particular holiday, such as always traveling for Christmas together or having met on New Year’s Eve, getting engaged on that day could add even more meaning to their love story.

For instance, a couple who bonds over their love of Halloween might find a spooky-themed proposal fits them perfectly. When done thoughtfully, these proposals can strengthen their love of the holiday rather than just using it as a convenient date.

When it comes to getting engaged on holidays or special occasions, there’s no right or wrong answer, but couples should ask themselves: Am I proposing on this day because it’s truly special to us, or because it’s convenient? The most important thing is that the moment reflects your love story, not just the calendar date.

Ultimately, whether you pop the question on a holiday or an ordinary day, what matters most is that the proposal feels authentic and meaningful to both of you. Some holidays are important in the timeline of a couple’s love stories and they make sense as engagement anniversaries, but if the feeling isn’t right, you can always pop the question another day.