Best Winter Proposal Stories

Christmas season is one of the most charming times of the year for engagements. Is there anything more picturesque than snow lightly falling upon two lovers as they promise each other their lives? We're here to make sure your winter proposal is as perfect as she is.

You may remember reading our earlier blog, 11 Unique Proposal Stories. This time we're focusing solely on the most popular time to get engaged, the winter. Below we have curated some of the best winter proposal stories we've ever heard, meant to help you plan your special moment.


Go On a Trip


"Jared and I have been together for almost six years now, so a winter proposal was a very long anticipated event for everyone we know. The past two years leading up to our engagement, I was asked at least weekly when Jared was going to pop the question, however he was very good at making sure that nobody figured out the surprise. Jared and I had not taken a trip together in a quite a while, so in December he suggested we go somewhere that I had never been; New York. Getting to New York was quite the adventure...nearly all of our flights were either cancelled or delayed, and we ended up going through security checkpoints 4 times because of all the cancellations (not an easy task for Jared with a ring in his pocket)! Jared reserved us a beautiful suite at the Mandarin Oriental Hotel overlooking central park in Columbus Circle; it was definitely worth the wait.

The day of our engagement was extremely relaxed. We had a late brunch, explored the MET, and afterwards sat at a coffee shop together, drinking hot chocolate and people watching for several hours. Around 5:00, Jared and I took a taxi to the skating rink at Rockefeller Center; myself having competitively figure skated for the majority of my life was extremely excited. We got on our skates, and hit the ice for about an hour until they called everyone off for the Zamboni. As I was skating to the exit, Jared grabbed my hand and asked to skate just one more lap. After our first last lap, Jared grabbed my hand a second time asking for yet another lap...I was very reluctant realizing that we were now the only two people left alone on the ice. It was after I realized this that the song, "Thank God I Got Her" started playing over the loud speaker, and I knew. Jared winked at me, got down on one knee in the middle of the rink, and asked me to spend forever with him. I said yes instantly and as we kissed, the Rockefeller Christmas tree started flashing all of its lights at once, and the nearly 500 people at Rockefeller Center that night started cheering. After the winter proposal, we were escorted off of the ice for champagne and photographs taken of us all around Manhattan.  Later that evening, we had an incredible dinner on the roof of the Mandarin Oriental, and to top it off, when we arrived back to our suite it was covered in hundreds of candles and rose petals, an extraordinary bouquet of several dozen roses, and of course…more champagne and dessert. This proposal was honestly like something straight out of a movie, and I am so exceptionally grateful to everyone who played a part to make it so perfect for us. Cheers to September 10, 2016, and the rest of our lives together as husband and wife!"


Go All Out for your Winter Proposal

Go All Out

"The Sunday before Christmas, Michael showed up in church with my family and I had no idea he was coming. Michael was on Christmas Break and I figured I would not see him until the next day for our family’s Christmas. He told me he came only to watch me play flute and spend the day with my family, since he didn’t have homework or anything better to do at home. I didn’t think twice about it until we sat down to eat dinner and he handed me a letter, telling me to read it before we ate….hmmm. Being given a letter was nothing unusual but the fact that I had to open it before I ate confused me. So, I read the letter and it said, “I couldn’t think of anything to get you for Christmas, so instead I am taking you on a Christmas date!” On the back of the letter were instructions which read, “1) Don’t eat too much because we are eating an early supper, 2) Dress warm because we would be walking in the cold a little ways to get to supper, 3) Be ready to leave at 2:30 pm, and 4) Just enjoy the surprise! I was ready to leave at 2:30pm and had a slight inclination of where we might be going. However, as soon as we turned to head south instead of north out of town, I knew my idea was wrong. We drove about an hour driving past Sioux City and I thought maybe we were almost to our destination. But when we exited toward Omaha, I really had no idea where he was taking me! Soon after the exit, he reached into the back seat and pulled out a hidden present, handing it to me. I was a bit puzzled because he had told me he wasn’t getting me anything. He assured me it was, “just one gift!” … so I opened it. Inside was a picture frame with the letter “M” and handwritten on it were all adjectives starting with the letter “M” that described me or our relationship. I had done something similar to this when we started dating in a letter that I wrote, so I kind of knew what he was doing but he only had done the first letter. We drove about another hour and he pulled out another present from the back! So I opened it and inside was the second letter of my name, “A”. Now I knew he was spelling my name and there were three more letters to come. We finally reached our destination, which was Omaha, NE, and parked. He told me to wear my warm coat because we would be walking a little ways to go eat. We hardly walked a half block to a fancy steakhouse, Omaha Prime, where he had reservations for supper. We sat down at the restaurant, ordered our food and as we were waiting for our food, our waitress brought a third present to our table! There was no way he had slipped it to her because I had been with him the whole time, so I knew there was extreme planning with this. Inside this one was the “R” picture frame AND two tickets to the Mannheim Steamroller concert that was at the Orpheum Theatre in Omaha that night!! He told me this was the real reason we were here in Omaha and we would be walking about eight blocks to get there which is why we dressed warm. We both love Mannheim Steamroller and I was so excited to go! But I was a bit puzzled as to where the other two presents would show up, even joking with Michael that I would have to go on stage at the concert to get one, but he assured me that wouldn’t be happening. We enjoyed a delicious meal and left the restaurant through a passageway which led right out to the street. Just in front of us was a horse and carriage with a line of people waiting to get their turn for a ride. Michael walked with me right up to the carriage and pointed something out, “Hey, look, there is a present inside the carriage that matches your other gifts!! That must mean the ride is for us!” We proceeded to budge, or so I felt, in front of the people in line. Once we got inside, he assured me that we weren’t walking to the Orpheum but rather getting a carriage ride to the front door. I opened the present that was on the seat and inside was the “I” in my name. We drove through the streets and the Lights Festival, where every tree on any street had Christmas lights; we both love Christmas lights! After being dropped off at the front door, we went to the concert, which was awesome!! After the concert, we were picked up by the carriage at the front door again and on the seat was the 5th present with the last letter of my name, “A”. I read it as we continued to drive through the Old Market. We rode through multiple more streets, looking and enjoying the Christmas lights which were all over! Finally, we came to an area that had a river running through the bottom and a bridge across it with LOTS of trees and lights! It was romantic! As we drove by, there was a guy standing by the bridge, and Michael pointed at him saying, “He has a gift in his hands that matches the other ones that you have opened. We better go get it from him.” So we had the carriage stop, got out and I walked to the gentleman to ask him if the gift was for me. I did not recognize him, but the man was Michael’s Great Uncle who lives in Omaha. He gave the gift to me willingly and Michael and I started to walk across the bridge. As we made it toward the center of the bridge, we stopped and I opened up the gift. I finally got the lid off and inside was lots of tissue paper and a piece of paper saying, “Maria Lynn, I love you!” Michael was standing behind me and asked what was in the box. I said, “Just a piece of paper that says, ‘I love you’”. He said, “No gift?!” I replied, “No, just the paper.” I turned around and he was down on one knee and said, “That’s because I have the gift right here!” He had the ring on his finger and it was dark but I could just see the diamond sparkling. It was beautiful! I could hardly believe it!! He asked me to marry him and I said, “YES!!!” We hopped back into the carriage and as it drove us back to our vehicle we smiled and laughed enjoying every little part of the moment!

Hit the Slopes

Hit the Slopes

Sarah and Justin were celebrating their 5 year anniversary by going on a vacation to Colorado. He figured it was the perfect place for a winter proposal. Justin had a horse drawn carriage ride waiting for them when they woke up the next day. As they went further into the mountain, they reached a little wooden bridge, and Justin pulled out a ring and asked Sarah to marry him, who gladly said yes.

Play A Game

Play A Game

December 10, 2016: This was the day of our annual "A Thankful Christmas Party". We have done this for a couple years and it's a time for us to get together between Thanksgiving and Christmas to hang out and have a good time. This year it was held at my house and I woke up early that morning to get everything else ready for the party. Zack had to go ref a basketball tournament that morning so he took off and I just went about my day. Later that evening everyone started to arrive and we were just having a good time eating and playing games. Well everyone was all sitting downstairs and we were ready to play the "Saran Wrap Ball Game". It is basically a big ball of saran wrap with goodies wrapped inside of it. Well we have played it every year and Randa (our close friend) said they put a twist on it by adding gifts on the inside that are labeled to individual people there. We start playing the game and eventually a "gift" gets thrown in my direction. I started to unwrap it and the ring box was not a normal square so I had no idea what it was until I opened it and saw the ring. My jaw dropped and Zack grabbed the box, got done on one knee and asked me to marry him. All I kept saying was "Is this a joke?!" It was the best day of our lives and I get to marry my best friend! The entire proposal was captured on video and I watch it almost every day!

Do You Want to Build A Snowman?

Do You Want to Build A Snowman

After an ice storm, Cody realized that the weather was telling him to take a chance on his winter proposal. Cody and Sarah decided to take an afternoon to play in the snow at the park they first met at four years prior. While gathering branches to make arms for a snowman, they ended up in an area of trees covered with snow and ice. In this picturesque setting, Cody started telling Sarah how much he loved her, got down on one knee, and went for his winter proposal.

Document the Moment

Document the Moment

"After lunch we went back Emma’s – I received a text from Sarah letting me know that the photographers were at the park, and that they’d be ready for us shortly. At the same time I received the text, Emma decided that it was a perfect time for a nap..ugh! I told her that I wasn’t tired and would just let her nap – so I showered and got ready for the night.

As I got ready she was trying to sleep, and I was making as much noise as possible so that she wouldn’t fall asleep – Emma was ready to kill me! After I was ready I told her that I was going across the street to get a coffee and wait for her to wake up from her nap. But really I was leaving so that I could walk across to the park, and I was going to call her on my way and tell her to meet me there. When I called her…she didn’t answer. Sleeping beauty decided that it was the perfect time to put her phone on silent so I had to run back upstairs to her apartment and pound on her door to wake her up.

I ran back downstairs before she answered the door and sent her a text telling her to go downstairs and get in Sarah’s car. Sarah drove Emma over to the park where I was waiting for her.

Once Emma arrived we walked over to a gazebo in the park and I got down one knee and executed my winter proposal…and most importantly, she said yes!"

Always Keep Her Guessing

Always Keep Her Guessing

How do you surprise a girl who knows her engagement ring is coming? That is the challenge Peter issued to himself when planning his winter proposal for Ellie. After picking a ring and diamond together a month before, Ellie had some time to wait while the ring of her dreams was being made. She watched for signs of anything out of the ordinary and waited for her turn.

When the day finally came, it was a rare cold day in March when the sky was blue and the wind was breezy. There were all the makings for a perfect winter proposal. Peter contacted Ellie’s cousin Kristina a few days before to assist in the evening filled with surprises. The girls’ had planned to meet after work and talk for a while. Soon after arriving at the restaurant and briefly saying “hello,” Kristina put down a full bouquet of colorful flowers from a local floral shop and a personal note both from Peter asking if Ellie would “travel life together” with him. She kept reading and the note requested for her to meet Peter at her favorite bench at Falls Park. Ellie was stunned and thrilled for such a surprise on the first day of spring.

While driving to Falls Park, Ellie had time to savor the moments as she experienced them. Ellie grew increasingly calm and confident that this was the moment she had been waiting for. Upon arrival, she bounded from the car and found Peter waiting, right by her favorite spot. After dropping to one knee, Peter proposed and Ellie immediately said “Yes. Forever and always, yes.”

Horse Drawn Winter Proposal

Horse Drawn Winter Proposal Picture

Michael had surprised Maria by taking her on a horse drawn carriage ride. Throughout, they made different stops where each letter of her name had a symbolic message. After taking her to dinner and a concert, they found each gift. The final gift was a box with a note saying "I love you," and as she turned around, he was on one knee, ring in hand.

It's time to go create the winter proposal of both of your dreams. Now that you have the proposal down, you also have to figure out which engagement ring and men's wedding band you need.

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