7 Holiday Proposal Stories That Are So Sweet & Festive, You'll Need A Tissue

If you’ve ever taken note that you see a whole lot of engagement announcements filling up your feed between Thanksgiving and Valentine’s Day, you aren’t imagining things. It’s no secret that the holiday season is super popular for proposals, and why shouldn’t it be? Between the twinkling lights, picaresque snowfalls, ice-skating hand in hand and cuddling by a roaring fireplace, there’s something inherently romantic about this time of year. Hence, holiday proposal stories tend to be especially touching.

So it should come as no surprise that a whopping 40 percent of engagements happen between November and February, according to WeddingWire. And a survey by Chillisauce revealed that 31 percent of people think Christmas Eve is the best day of the year to pop the question, while another 19 percent said New Year’s Eve is the optimal day, and 16 percent think New Year’s Day is the ideal time.

The holidays are all about gratitude for what you have and excitement around what’s to come in the new year, so it makes sense that this time is chock full of super romantic proposal opportunities. You know, the kind that makes you feel all the feels, pop in your favorite Hugh Grant movie and induce a major case of diamond fever. Alas, here are just a handful of heartwarming true tales to keep you warm this holiday season.

The Private Concert
We had gone into a New York City to see the Radio City Christmas show and see the tree in Rockefeller center. We saw the show and the tree and decided to walk back to Penn station instead. Took a detour through Bryant Park and there was a street performer playing guitar. He was playing Foo Fighters' 'Walking After You,' which got my attention since it’s one of my favorite songs, and then Ed Sheeran's 'Thinking Out Loud' started.
Next thing I knew, he got down on one knee to tell me how much he loved me and how he wanted to be with me forever and then pulled out the ring. I, of course, said yes and the crowd around us began clapping.
It turned out he planned it all. The street performer was a friend of his that he got to play, and had a photographer friend there as well to capture it. The proposal picture is now framed in our apartment because it’s an amazing shot.


"Where Dreams Come True"
Hubby made my dream proposal at Disneyland, but instead of it being on the carousel, he did it in front of the giant Christmas tree after all the lights lit up. It was pretty amazeballs.


A Very Private Proposal
We were at home, about to get ready to go out for dinner, just the two of us. I suspected it might happen that night because he had made the dinner reservations himself (rare), but he wasn’t acting weird or anything. I thought it might happen at dinner.
As I came into the living room, he told me we had forgotten to pack up one of the gifts from under the tree to take to his parents for Christmas. Upon closer inspection, he’d hand carved a box, wrapped it in a ribbon and placed it in the tree. He got down on one knee. I blacked out. He said some things. I said yes. He put a ring on my finger. It was perfect and private and sweet.


The Stocking Surprise
It was Christmas, and we usually open the stockings first in my family. My now-husband insisted we do them last (at that point, I was suspicious because I can read people very well). We opened our gifts, they opened their stockings and then I got to open mine. One by one, I took everything out and then got to a jewelry box. In my head, I told myself, "Well, this is it" and I took a deep breath and opened it... and it was a pair of earrings.
I kept going through the stocking and the last thing was also a jewelry box. I was so sure, but then I took it out, held it in my hand for a moment, studying it and then my husband got down on one knee as I opened it and asked me to marry him. I stared at it for a few seconds and then up at him, all teary-eyed and said, "YES."


Popping The Question Like a #BossLady
I liked it so I put a ring on it. I snuck out the day after Christmas last year and bought him a ring. I cooked him a nice meal with a bottle of wine, and when he asked what the occasion was, I busted out the ring and said it was to celebrate our engagement.


The Ol' Wrapping Paper Trick
She knew I was proposing soon, but not when. Neither of us wanted a big public showing, as that’s not like us. So rather than do anything that would make her suspicious, I decided to go for it when we were opening our Christmas gifts to one another. When we were done, I got down on one knee under the pretext of grabbing wrapping paper and came up with the ring instead.
Definitely caught her by surprise, even though she knew it was coming soon. Still vaguely proud of that one, she’s usually too quick for me to pull one over on her like that.


Mistletoe Memories
We had just gotten back from a romantic weekend getaway at a cabin in the woods. We came home and decorated our tree. While I was hanging up the mistletoe he came over and kissed me. Then he just kind of plopped down on one knee and stammered it out. I started crying and hugging and kissing him immediately and he pulled away and went, 'Is that a yes?' lol. Of course, silly head. He had apparently had the ring with him all weekend and kept chickening out.


The Festive Fake Out
I was showing my wife pictures of some really cheap rings while I was actually buying her one that was pretty nice. Also, I had her (sort of) convinced that I wasn't going to ask her and that I was going to wait a lot longer.
On Thanksgiving Day, we had dinner, then drove with two of our friends (not a couple) to Las Vegas. I tried to get on the gondola ride, but it was closed, so the next night, at the fountains in front of the Venetian, I proposed. Our friends didn't know about it until that point. My wife told me (sort of jokingly) that if I didn't ask her by New Year's she was considering asking me. We've been married for six years now.


Is a diamond ring on your holiday wish list this year? Well, then these seriously sweet proposal stories should provide a little inspiration. There are so many ways to pop the question this time of year, and regardless of where, how, and when it happens, it’s bound to be downright magical. From low-key proposals while snuggling at home to grand public proposals by glamorous Christmas trees, there’s honestly nothing like two people committing to a lifetime together to get you in the holiday spirit. Now excuse me, I need a tissue.