Why the Holidays are the Best Time to Get Engaged

Nov 18, 2022 | marriage, Wedding

Thinking about getting engaged? You’re right on time. The holiday season is upon us, and there’s a multitude of solid reasons why the holidays are the best time to get engaged. They’re also the most popular time to get engaged, and for a good reason. In fact, in 2015, Facebook reported that “2.6 million people in the US alone changed their relationship status to ‘engaged’ between Christmas Eve and Christmas Day.” Moreover, 15.5% of engagements happen in December, more than any other time of year. No other month claims more than 9% of engagements. 

Whether you celebrate Thanksgiving, Christmas, Chanukah, Solstice, or anything else around this time of year, it’s an excellent time to plan your future, solidify your commitment, and take the next step in your relationship. Here’s why.

Family Involvement

If you’re close to your family, you might take joy in including them in your engagement–and the holidays are the time when families are most likely to get together. Propose to your spouse in front of your closest family members and/or friends. Get your family involved in setting the scene by telling them in advance what’s going to happen and giving them roles, such as preparing the space, distracting your future fiance while you shop for a ring or otherwise get ready, allowing them to say a few words, or simply being there as witnesses to your engagement.

This isn’t just a fun way to propose; there are actual benefits to involving your family. For one thing, your partner will feel welcomed into the family from the get-go. For another thing, coming together to co-create or be a part of such a joyful event reinforces and strengthens family relationships. Also, involving your family sends the message that they’re important to you, which builds trust and even helps to repair past wounds. 

An added benefit is that family from both sides are more likely to have time to meet during the holidays, which means that if they either haven’t met yet or haven’t gotten to know each other very well yet, a holiday engagement can help them get to know each other better and also begin to collaborate on wedding planning. 

Proximity to Vacation

No matter what traditions you embrace, if you live in the USA, you probably have a job that gives you time off at Christmas. Therefore, proposing around holiday time means that you’ll get to celebrate together by taking a vacation soon afterward. A vacation as a newly-engaged couple is something special. It also gives you the much-needed time and space you need to start planning your marriage. In fact, it’s also an ideal time to start talking about your prenup


You know how sometimes you really want to cuddle, but it’s a summer evening, and you’re up to your armpits in your own sweat and even holding hands proves a slippery affair? Not so nice. However, compare that to the pleasure of cuddling when it’s cold outside, and you’re warm and cozy together under the blanket. You’re probably gonna want to have some nice close snuggly time after you get engaged, and it’s going to be much nicer during the holiday season when temperatures have dropped enough to make your partner’s body heat a welcome prospect.

Also, if you live somewhere that gets snow, there’s something particularly cozy and romantic about a snowy evening as a backdrop for an engagement. 

New Beginnings

People tend to associate the holidays with starting a new chapter, especially when it comes to New Year’s. An engagement is a positive and promising way to begin a new phase in life. Getting engaged at a time when people are feeling connected to the idea of turning over a new leaf also means they may have extra motivation to work towards relationship goals and settle old conflicts. 

Tradition and Ritual

The holiday season is all about embracing traditions and rituals, whether they come from your culture, your family, or you as an individual. Engagement itself is not only a ritual; it is one of the most exciting experiences of one’s life. Therefore, it makes sense to get engaged during a time fueled and inspired by ritual. Plus, getting engaged means that you’re going to be embarking on a new journey together, and it’s the perfect time to create new rituals together.

Epic Places to Get Engaged

The holidays are rife with amazing settings in which to get engaged. Think pumpkin patches, hay mazes with your bae waiting at the end with a ring, snowy landscapes, frozen ponds for ice skating, apple orchards, Christmas tree farms, or even underneath the Christmas tree. If you choose to get engaged with one of these magical settings as a backdrop, you’re also potentially creating a new ritual. The two of you will always associate that setting with your engagement, and it will be a beautiful reminder every year into the future whenever you’re in a place like that.  

Who SHOULDN’T Get Engaged During the Holidays

One must not forget that for many people, the holidays are actually a sad time. Sometimes they’re marked by painful anniversaries. Sometimes they mean intense conflicts with loved ones. Getting engaged at such a time could feel off, like trying to force excessive joy during a time when it doesn’t come naturally. That said, some people for whom the holidays are challenging may see engagement as a way to make new memories and reframe the feeling of the season. If this is you, we support you! But just know that there’s also nothing wrong with holding off and getting engaged at a time that feels lighter to you if the holidays are a difficult time. 

What Else You Should Do During the Holidays

Get a prenup

You know what goes hand-in-hand with engagement? Prenuptial agreements! As luck would have it, the holidays are not only a great time to get engaged but also a perfect time to get moving on a prenuptial agreement. 

Before going into why that is, take a moment to reflect on the necessity of prenuptial agreements in modern relationships. Marriage is hella romantic, but it’s also a financial partnership. Some couples make mistakes when they get engaged by minimizing the focus on the financial aspect of marriage while maximizing focus on pursuits that might feel more exciting at the moment, like wedding planning and romantic getaways. However, at its core, marriage really is a financial partnership, and planning accordingly can help stack the odds in favor of marital success.

That’s where a prenuptial agreement (or prenup, for short) comes in. It opens up communication about an array of financial topics you might not have considered before, including your financial goals, roles, and expectations in marriage. These are things you’re going to want to sort out before the wedding, not after. Making sure all is clear on the finance front is a fantastic way to prevent a conflict that will inevitably arise later if you don’t see eye to eye on finances and don’t talk about it. 

Ask family for advice

As aforementioned, the holidays are a time when you’re likely to be around family and friends–and your family and loved ones might have valuable insights to share. Got a great auntie and uncle whose relationship is still going strong after 30 or 40 years of marriage? Find out if they wrote a prenup. If so, find out what they included, how it has served their marriage, and what they would do differently if they were writing it again for the first time. 

Additionally, parents love being asked for input on such matters–especially since boomer parents have a penchant for wanting to be involved in their millennial children’s prenup talks. If you don’t want you or your partner’s parents to be involved in this discussion, don’t sweat it. However, if you already feel that your in-laws respect your boundaries, you might consider asking them for their insights. Doing so will make them feel valued, which will increase their support of your relationship. There’s a good chance it could also yield some unexpected and sound advice. 

Use your holiday vacation time

The holidays are also an excellent time to talk about your prenup because the holiday season is often accompanied by vacations. Your prenup is one of the most crucial documents you’ll ever sign, and it’s important to take a careful and deliberate approach to craft it. It shouldn’t be rushed, and it shouldn’t be done when you’re distracted or under stress. Pre- or post-holiday vacations are, therefore, an ideal time to have these important prenup discussions because you’ll likely be feeling relaxed, you’ll have space in your mind because it won’t be full of work deadlines and to-do lists, and any disagreements will likely be weathered more gracefully than when you’re also facing the day to day trials of everyday life. When you’re not stressed, you can discuss that stuff in a collaborative and level-headed way. It also doesn’t hurt to be basking in the glow of a new engagement as you navigate prenup discussions! 

How HelloPrenup can help

We recommend going through HelloPrenup’s customized prenup software. The platform guides you through all the essential decisions you need to write into your prenup and gives you options for many different clauses you might include (or not). Both partners fill in their details and prenup preferences separately, and then the platform alerts them of any discrepancies so that they can discuss their differences and then finalize, print, sign, and notarize the agreement.

If both partners begin the process during a vacation and continue until they’ve filled in all details and discovered where their differences lie (if there are any), they can take time during their vacation to truly understand one another’s position, sort out compromises, and collaborate on solutions that make both of them happy. Time and presence are crucial keys to this process; when there’s enough time to honor the process and when both partners are able to be fully present with it, negotiating differences in prenup preferences can be a truly excellent team-building activity for partners, bringing them closer together, and help prepare them for a lifetime of marriage. 

In case you’re not convinced yet, HelloPrenup has a Black Friday discount offer on prenups this holiday season. Just create an account, go through the steps, and use the code Take50 at the checkout. 

You are writing your life story. Get on the same page with a prenup. For love that lasts a lifetime, preparation is key. Safeguard your shared tomorrows, starting today.
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