The Holiday Proposal Checklist

Wifeys & Gentlemen,

We have reached that time of year where, depending on your age group, you might be seeing a lot of newly engaged couples on your timeline. Believe it or not, Thanksgiving, Christmas, New Years Eve, and Valentines Day are some of the biggest days for marriage proposals. Brides Magazine estimated that approximately 33% of couples get engaged on a fall/winter holiday!

In the past, I know I’ve posted rather strong opinions about holiday engagements. Please believe, I am NOT judging them, I’ve just always felt like they were a bit of a no no. In fact, many of the women in my life have expressed similar sentiments, believing that a holiday proposal felt more like a copout or a cliché than a special moment they’d remember forever.

I asked my husband, Mr.B, and while he understood why some guys might choose this time of year to pop the question, he decided it was better to avoid using a holiday as the backdrop for this life-changing moment.

Usually, I would use this time to tell you all of the reasons why you probably shouldn’t try to get engaged on a major holiday but, as I’ve mentioned countless times already, this year is so different. I would never want anyone to feel like I am 💩ing on their romance! 2020 has taken so much from so many of us. If you are blessed enough to have love in your life and are feeling joyous enough to take that leap, you should do it on whatever day means most to you, even Christmas!

Instead, I wanted to submit a little “checklist” of sorts. This way, anyone who is thinking about doing a holiday proposal has a bit more information before committing to going through with it.

My 2 cents:

Know your partner & their expectations…

Part of the reason why I can be a little harsh about holiday proposals is because I personally would have been a little disappointed in one. Even though Christmas is my favorite holiday, I always had a picture in my mind of how my man would pop the big question and Christmas morning just never entered the chat! That isn’t to say that if he would have asked on a holiday that I would say “no”, but I’d be a little crestfallen at the notion that after 2.5 years of being together, he didn’t listen to me or know my personality as well as I’d hoped. This is likely NOT the case for everyone, so just make sure your partner is the kind of person who would love a holiday proposal! Have they dropped special hints? Have you put the feelers out to know if this is something they’d respond positively too? If the answer is yes, proceed! 😉

Try to make the moment your own…

Going back to my first point, if you’ve made sure that your partner would be down for a holiday proposal, now its time to create the moment and make it special. Try to pick something that enhances as opposed to something that might be overshadowed by the day’s importance. If you’re spending time with family and friends, it is also a good idea to make sure no other proposals are intended for that day (unless you/your partner doesn’t mind or it was part of your master plan). Basically, you want to make to make sure that your proposal is still romantic, unique, and special enough to create an amazing memory. Don’t let it be an afterthought or so nonchalant that it feels routine. Shake things up a bit so you both can tell this story at holidays to come!

Get clear on public vs private proposals…

This is good advice regardless of your chosen proposal date. I might be a weirdo, but I did not want an audience at my proposal (not even a hidden photographer). I wanted that time to be something special and intimate between me and my man. However, I know I am in the minority on this! Many people like to be surrounded by friends and family when this question is posed. If your partner is into public displays, make sure you let the guests know and do your proposal in front of everyone! You might even find a way to get your loved ones in on the fun. But, if your partner is more like me, try to do something that is away from the public eye. Give your partner a chance to surprise everyone with the news! There is also a happy medium. Maybe your partner doesn’t want EVERYONE to be there, but they might want a few select people around. Maybe they don’t want a grand public gesture but they don’t mind a few strangers passing through (ie: if you propose in a local park or at a nice restaurant, etc).

Be prepared for something to go wrong…

I have already told ya’ll not to even think about proposing unless you are at least 85% sure your intended is going to say “yes”. Of course, you should always try to be ready for the possibility that they could say no, but that isn’t exactly what I’m talking about here. Let’s say you plan a perfect Christmas morning proposal and you know your partner is going to be surprised, happy, and ready to say “yes”. There is a chance that with the chaos that often comes with holidays, something might go wrong. My engagement was on a random day in July (the 14th to be exact) and it still didn’t go exactly as my husband planned! It’s totally fine and our story still makes me smile, but I warn you to try to expect the unexpected, especially if other people get involved.

Make sure to have time for yourselves…

The day we got engaged was amazing! I told my parents and we might have told a few friends (can’t recall) but we spent the rest of the night and the next day together, just the two of us. We had an amazing dinner, cuddled up on the couch for tv, and went to get ourselves mani/pedis the next day so we could show off our new rings (my husband got himself one too). If you’re going to propose on a holiday, there is typically a lot of hustle and bustle. Even if you are unable to be with all of your usual people, there are still events and traditions that most of us like to stick too. Even if Christmas trivia night is done via zoom this year, it still counts as a distraction! Clear some downtime for the two of you to bask in the newly engaged glow. You’ll have a rush of endorphins and serotonin, which will make you want to spend time with your love and soak up all of the closeness. Even if it’s the next day, just make sure there is time set aside that is just for the two of you.

Of course, this isn’t everything! Proposals take work no matter what day you decide to go through with them! Make sure you are prepared, have your ring picked out (or whatever token you’d like to use), and don’t try to use the holiday as a copout for putting in the effort. Also, because Christmas is just around the corner, let me be the first to tell you that a proposal should NOT double as your Christmas gift. Now, if you spent most of your money on a ring, that’s fine (though I always recommend spending a few months saving up for one so this doesn’t happen). All I am saying is that it is possible to still do your usual Christmas with a proposal on top. Buy your partner some little nicknacks or do some DIY projects to make them feel special for the holidays if you can. Check out my holiday gift guide if you need some last minute ideas.

Also, I want to close by saying that even though I know a majority of my readers are women, I am writing this blog for EVERYONE; men, women, non-binary folks, members of the LGBT community…EVERYONE! I respect traditions for what they are, but anyone can propose these days!

Still, feel very free to share this article with the man in your life…you know…just in case ;-).

Until next time,

Carry on Wifeys & Gents!


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And as always…

Be a lamb and tell your friends! Especially if they are close to popping the big question.

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