With the holiday season in full swing and the new year fast approaching, it’s easy to get caught up in all the romance. The colder months are often called “cuffing season” for a reason and there’s no doubt that spending the holidays surrounded by romance with your partner can make you feel like you absolutely have to propose before 2019 officially begins—especially if you’re seeing a lot of other couples get engaged. Around 40 percent of engagements happen between Thanksgiving and Valentine’s Day, so it’s very possible that hearing your friends talk about their recent proposals and seeing rings on your Instagram feed is inspiring these emotions.

If you’ve been thinking about popping the question before January rolls around, here are a few questions you should ask yourself first.

Am I doing this just because it seems like everyone else is?

If it feels like the pressure is on because several of your friends just got engaged during the holiday season too (or you know they’re planning to propose), it might be worth pausing.

You don’t want to go into your proposal motivated by outside factors and comparing your relationship to others. There’s nothing wrong with choosing this time of year to ask your partner to marry you, as long as you’re doing it because you feel ready to take the next step and you think your partner will agree.

It’s important to take a moment to reflect on why you feel so eager to propose now, especially if these feelings are newer and you weren’t planning to get engaged a few months (or even weeks) ago.

Is this time of year and setting what my partner and I want?

Proposals should really be about the two people involved—you and your significant other. Depending on whether you plan to propose to each other or not, you might have something planned that’s totally all about their dream proposal or it could incorporate things you both really love.

Your proposal should really be based on what will make you both happy, at a time of year and in a location that makes sense for you and your relationship. If your partner is a quiet, shy person, a public grand gesture probably isn’t the right fit. And if you and your significant other hate the cold, you might want to rethink proposing in the winter right before January starts.


If you’re thinking of proposing because the end of the year has made you think about the time you spent with your partner and how your relationship grew, that’s great! Just make sure to take that energy and refocus it toward crafting the proposal that’s right for you as individuals.

Am I setting up unrealistic expectations for this time of year?

We can all get swayed by the stress and magic of the holidays-into-new-year season, with all the manufactured consumerist sparkle and cheesy holiday romcoms. It’s a time of year when we’re socialized to expect (and adore) grand gestures and sharing the season with a romantic partner.

“When one fuses the holidays with one’s proposal/engagement, one unfairly burden it with one’s history,” explains Mark B. Borg Jr., a clinical psychologist and a certified interpersonal psychoanalyst. People who choose to propose during the holiday season are going to tie their engagement to that time of year. If you or your partner have negative feelings about the holiday season, those feelings will cloud your engagement. And even if you have positive feelings, Borg says, it creates “heightened expectations—often ones that set the bar high, and lead to unfair comparison and disappointment.”

Instead, a proposal should happen at a time when you and your partner can appreciate the moment as a singular event, according to Borg. “An engagement/proposal needs to be its own special, idiosyncratic, one-of-a-kind experience,” he says.

And the holiday season doesn’t need to be all about your romantic relationship if that helps you let go of the idea that you need to propose right now. You can spend this time of year more focused on friends, family of origin and chosen family, if you want, and then set aside more romantic one-on-one time with your partner when you’ll both feel less stressed. Besides, if you go into the season with extremely high, rigid expectations, you’re setting yourself up to feel extra stressed out about the results. It might be better to take the pressure off and actually enjoy the holidays and worry about your proposal at a time of year when you don’t already have societal expectations so built in.

If you go through all of these questions and still feel committed to proposing, go for it! There are so many romantic things about this season, like horse-drawn carriage rides, ice skating and snow. Whether you’ve been planning this all year or you spontaneously decided to buy an engagement ring last month, make the proposal one that you and your partner will remember—and talk happily about—for years.