Holiday Proposal Season: The Sweet (and Funny) Things We Do When We Think It’s Happening

Holiday Proposal Season: The Sweet (and Funny) Things We Do When We Think It’s Happening

There’s something magical about the holidays. The lights are twinkling, the air feels a little crisper, and everywhere you look, love seems to be in the air. It’s no surprise that Christmas Eve, Christmas Day, and New Year’s Eve are some of the most popular days of the year for proposals.

And if you’ve ever suspected this might be the moment… we’ve all been there.

When I was expecting a proposal, I suddenly became very intentional about the little things. My nails? Always freshly done and perfectly polished, because you never know when a ring photo might happen.

Neutral shades, timeless colors… something that would look beautiful forever.

Outfits were carefully chosen. Hair appointments scheduled a little closer to the holidays than usual.

Jewelry swapped out for pieces that felt extra special. It wasn’t pressure, it was hope. Excitement. That quiet, happy feeling that something wonderful might be right around the corner.

Then my daughter Brooke shared what might be one of the most modern proposal-season tips I’ve ever heard.

We all joke that our phones are always listening. Mention something out loud, and suddenly it shows up everywhere on your screen. Brooke decided to use that to her advantage.

She would lean over and whisper into her boyfriend’s (now husband) phone: “Engagement ring… engagement ring… engagement ring.”

I thought she was absolutely genius.

Naturally, I followed her lead whispering “Engagement ring… engagement ring… engagement ring” and the diamond cut I loved most into my then significant other’s (now husband) phone whenever I had the chance.

Was it foolproof? Who knows. But it felt like it was needed at the time.

The Overanalyzing Begins

Holiday proposal season has a way of turning even the calmest among us into detectives.

Why is he making dinner reservations?

Why is he suddenly nervous?

Why are we taking a walk right now?

Why did he casually ask what size ring I wear?

Every moment feels meaningful. Every plan could be the plan. And somehow, the waiting becomes part of the magic.

When It Doesn’t Happen the Way You Imagined

I’ll let you in on one more secret. My own proposal didn’t happen the way I had planned in my head.

Almost five years ago, we were on a two-week vacation, one week at a dude ranch, the second week at the beach. Every beautiful destination, every perfect day, every (my) perfect moment, I was sure this was it.

And when it didn’t happen… day after day… “the talk” we were going to have when we got home was forming in my head.

By the last night of the trip, when all the wonderful experiences were over, I was convinced it wasn’t coming at all. He asked if I wanted to ride into town, and I couldn’t care less.

My hair was a mess from the beach. An outfit was thrown on. And my attitude? Slightly worse.

And that’s when it happened.

It was a reminder I’ll never forget. Sometimes, no matter how much we plan it in our minds, it isn’t our plan, it’s theirs. And somehow, it always ends up being perfect anyway.

So yes… prepare. Do your nails. Choose the outfit. Whisper into the phone.

But leave room for surprise, because the most meaningful moments often come when we least expect them.

From “Yes” to “I Do”

After the excitement settles, the happy tears dry, and everyone is told the wonderful news, thoughts naturally turn to what comes next: the date, the venue.

At Raintree, we love being part of that next chapter. From elegant indoor space to breathtaking outdoor scenery, your dream wedding awaits at Raintree. A setting designed for unforgettable moments, heartfelt celebrations, and the beginning of forever.