Do’s and Don’ts for Holiday Engagements

As we settle into the holiday season and fresh snow begins to fall on the mountains and pines, it’s hard not to get wrapped up in the merriment of it all. Holding that special someone close during the coldest, darkest months of the year can also lead to some intimate moments that, if properly taken advantage of, can be the perfect opportunity for a romantic holiday engagement! So, we thought it would be the perfect time to offer some advice on how to go about popping the big question in the most festive way possible. Here are some do’s and don’ts to follow to ensure that your holiday engagement will be merry, memorable, and most importantly, successful!


  1. Use the Season to Your Advantage:

    The holidays are always a magical time of year, and it’s important to keep that in mind if you plan on proposing in December. You will want to try and capture the spirit of the season by making it a focal point of your proposal. We recommend that you lean into the festivities and use them to your advantage. There are a lot of great opportunities here, whether it’s at a holiday party in front of everyone, driving around the block to look at Christmas lights, or cozying up by the fire, just you and the one person that you love the most.

  2. Do it Before the End of the Season:

    If you plan to get engaged during the holidays then it’s pretty important to get it done before they’re over. As with anything related to the Christmas season, waiting till the last minute won’t do anything but add stress to the situation. It’s also good to keep in mind that as Christmas grows near, things tend to get that much more hectic, so be sure to pick a date that won’t interfere with any of the festive plans that your partner already knows about.

  3. Make Sure You Leave Room for a Private Moment:

    Whether you decide to propose in a more intimate setting, or to make it a public display for all the world to see, it’s important to set aside a short time for just the two of you. There’s a lot of emotion that comes with asking someone to spend the rest of their life with you, so it’s always good to be able to slip away for a few brief minutes after the question has been popped. Leave yourselves time to relish the moment and embrace in the promise and joy of your new lives together.


  1. Don’t Go to Cheesy with It:

    In these situations it can be all too easy to fall into some of the holiday traditions and cliches that we all know and love. However, if it’s too over the top then the sentiment of the moment might be lost in the pageantry, so be sure to keep it fun, yet tasteful. Those big romantic gestures can certainly be dazzling, but they don’t always make for the best holiday engagements, so remember to try not to get too cheesy with it. After all, this isn’t a Hallmark Christmas movie!

  2. Don’t Propose in Front of the Family (Unless you know they’ll love it!):

    When considering a Christmas engagement, there can certainly be some treacherous waters to navigate. One of the biggest things to consider is whether or not you want to propose in front of family members. This can be a tricky situation and one we recommend avoiding if at all possible. There are some exceptions to this rule, i.e. you know her family well and know that they would absolutely love it, but if that’s not the case, then this isn’t the move for you. People can be very particular about their holiday traditions, and if you think that your proposal might disrupt them then it’s best to just play it safe and keep the moment private. Plus, then you get to partake in the fun of making an announcement together.

  3. Don’t Make the Holiday all About the Proposal:

    A wedding proposal is a big deal, and a romantic gesture like that can overshadow other events, people, and festivities. If you are trying to get engaged over the holidays, then it’s always a good idea to make sure that you’re not imposing on any of your partner’s favorite holiday traditions. It’s best to try and make the season special regardless of the proposal, and instead let it be the cherry on top of the fruitcake!

Holiday engagements are a fun and festive gesture of true love that can help set you and your significant other up for a lifetime of love and compassion. However, as you have seen, it is important to avoid some of the pitfalls that can come with trying to pop the question during the busiest time of the year. A gorgeous winter wonderland of a proposal is sure to make for a romantic and memorable moment between you and the person you care about the most, but be sure to take their feelings and preferences into account when planning it. Once you’ve finally done the deed and are betrothed to the person of your dreams, be sure to make your way back to Longmeadow so that we can help you plan your big day! Happy Holidays and Merry Christmas!


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