Cutest Christmas Proposal Ever | Brittany and Tim

How We Met: Our love story began on a cold and snowy December day. I looked at Tim and I just knew that I had to strike up a conversation with him. So I typed up a somewhat witty, somewhat awkward message and the rest is history. That’s right, our love story began over the internet. Romantic, I know. But it gets better, I promise.


After sending a few messages back and forth, I decided that enough was enough and I proposed that we should just meet in person. Admittedly, half the reason was that I was getting lazy and tired of writing long messages. But my motivation was also coming from the fact that I was really intrigued by this mystery man and I was too excited to wait for him to ask me out. My boldness paid off as we went on our first date shortly after and to say that we hit it off would be an understatement. We met one chilly January evening at a cozy café in downtown Oakville. After my initial blurting out, “I’m really nervous”, and his, “Don’t worry, my heart is racing”, we broke the ice and chatted and laughed the night away. We learned that we both shared a deep love for our families, dreamt of traveling the world and were grounded in our relationship with God. The conversation flowed so naturally that we chatted nonstop until eventually the barista came over to inform us that they were closing. With a big smile on his face, Tim walked me to my car and hugged me goodbye. I left that night feeling like that had been just the beginning of something beautiful that God had in store for us.

Tim and I shared many memorable moments over the next 12 months of our courtship. Tim is from the East Coast of Canada, so we went on a couple of road trips to visit his friends and family. We would spend 15 hours driving there and 15 hours driving back! That is a long time when you are stuck with the same person in a little car! It was during those long trips that we bonded and shared some of our deepest thoughts and feelings. It also tested us to see if we could handle each other for that long in close quarters. Well, we passed that relationship test!


The more time I spent with Tim, the more I fell deeply in love with him. He made life more exciting and constantly had me laughing. Tim was also very patient and loving with me as I slowly let down the barriers that I had put up from a past painful experience in my life. I saw so many qualities in him that I had hoped for in a future husband, so I prayed for God’s direction in our relationship and waited to see what would happen.


how they asked: Ten months into our relationship we started to browse around for engagement rings. We found one that we both loved and I knew that a proposal must be around the corner. Time passed and soon it was Christmastime. We were spending Christmas away with Tim’s family out east. It was a pretty big deal as it was my first Christmas away from my tight-knit family and Tim truly appreciated the gesture. I had a feeling that Tim might propose over the holidays, but the trip came and went with no sign of a proposal anywhere in sight. I waited patiently (for the most part), and then before I knew it, our one year anniversary arrived.

Our anniversary fell on a Friday, so we spent the evening together at Tim’s house. Being budget conscious, we opted to make a fancy dinner ourselves instead of going out to eat. As our dinner came to an end, I half-jokingly said to Tim that I had thought that he was going to propose that evening. He laughed and rolled his eyes saying that it would have been too cliché. I agreed and didn’t think much else of it.

The next evening while I was at work, I received a text message from Tim. He said that he wanted to take me out somewhere nice after church on Sunday. His reasoning was that I had cooked dinner for him on our anniversary and now he wanted to do something special for me. He suggested that we go to a wine bar as we had never been to one together and he knew that I appreciated a nice glass of wine every now and then. I thought that it was a sweet idea and I was looking forward to our little belated anniversary celebration.

The next day I woke up early for church as I was scheduled to volunteer with the kids that morning. I brought along a change of clothes as I knew that we were going out afterwards. My morning started off great as I volunteered with the babies in the nursery that day and everyone who knows me knows that I love babies. After volunteering, I went to look for Tim. He was scheduled to help out with sound for the services that weekend, but I couldn’t seem to find him anywhere and he wasn’t answering my text messages. I thought that it was strange, but I asked around and eventually someone else from the production booth told me that he had went upstairs to do something. I later found out that guy was in on the proposal and was covering for Tim. With the 11:15 service starting and Tim nowhere in sight, I went and sat down for the service with one of our friends.

Throughout the service, I kept glancing back at the production booth and there was still no sign of Tim. Part of me was a little worried, and the other part of me was excited and thought that something was up. But I didn’t want to get my hopes up, so when Tim finally texted me near the end of the service I didn’t think much of it. He apologized for leaving me hanging and told me that the production manager had him running errands around the church that morning. He also explained that his phone was not working properly and it wouldn’t send any of his messages all morning. I later found out that was actually the truth and that he was getting really stressed as a lot of people were relying on his cues for the proposal that day.

After the service ended, I went and got changed for our date and off we went to our first stop. Tim took the long way to get to the wine bar, and when I questioned it he told me that he just wanted to take the more scenic route. We blared the radio and danced being our typical silly selves as we drove through a pretty snowfall. When we finally reached the wine bar, I noticed that the parking lot was empty. I told Tim that I had a feeling it was closed, so he went to check out the situation as I waited in the car. Sure enough, he came back looking disappointed. The wine bar was closed and we would have to go somewhere else. Tim later told me that it had not been part of the plan and that he didn’t realize it would be closed on Sunday afternoon. We both brainstormed about where else we could go and Tim suggested that we go to the Green Bean, the café where we had our first date. I thought that it was a cute idea and agreed that we should go there.

We drove to the café and enjoyed a nice lunch and a couple of delicious warm drinks. Tim could only finish half of his lunch, and if anyone knows anything about Tim, the guy loves to eat! I pointed out that it was strange, but he told me that the flavouring was strong and he could only stomach eating half of it. I had a funny feeling that something was going on, but again, didn’t want to get my hopes up. We finished up lunch and left the café. Once we were back in the car, Tim informed me that there was one more place that he wanted to take me. So off we went for another drive.

We drove for a few minutes and it seemed like we were out in the middle of nowhere. I wondered out loud where he was taking me, but he told me that it was a surprise. At that point, I was getting pretty excited as I had a feeling that something big was going to happen. We pulled into the parking lot of what appeared to be a garden centre. I was a little flustered and confused, and Tim wasn’t saying a word. I turned to Tim and said, “What are we doing here? Are we going to buy a discounted Christmas tree for next year or something?” He laughed nervously and just kind of smiled at me and then looked away. Like I mentioned before, I had a feeling that something might go down here, so I quickly applied another coat of my favourite lip gloss just for good measure.

We walked into the garden centre holding hands and it was almost entirely empty other than the employees who worked there. Tim led me towards the back of the store where there were lots of pine trees off in a secluded area. At that point I was a little confused as to what was going on, but then something beautiful caught my eye. I turned and saw the most romantic arrangement of pine trees decorated in twinkly lights and photos from our relationship. I was overwhelmed and I immediately burrowed my head into Tim’s chest. I couldn’t even utter a word as I was so taken aback. It was perfect.

engaged at christmas


Tim, grinning from ear to ear, then proceeded to tell me that he was going to take me for a walk down memory lane. He explained that he had prepared this indoors due to the cold weather, and that he still wanted to incorporate nature, something that we both appreciate and enjoy. I was still flustered, and asked him, “What did you do all of this for?” He said that it was just a little something for our anniversary. There were around a hundred photos strung with red yarn across beautiful twinkly light covered trees. Of course it was for something much more, as this was not your typical anniversary celebration!


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Tim pointed out the first couple of photos. They were taken back in university and during my backpacking trip before we had ever met. He then showed me the first photo that we had ever taken together and we smiled at the fond memory of going skating together. He then proceeded to walk me through the story of our relationship told in a carefully arranged timeline of photos. He gave a candid little commentary on each photo that we came across and we both smiled and laughed as we looked back on the memories that we had created together. My heart was racing and I couldn’t stop smiling and burrowing my head into his chest. All of this was for me? I felt like the luckiest girl alive.



As we walked along the trees, I heard the familiar clicks of a camera. Sure enough, through the trees, I caught a glimpse of a grinning photographer who was clearly right in her element. It was Jess, a new friend of ours, and she was capturing the whole thing! Tim knew that I was a very sentimental person who appreciated the gift of photos and being able to re-live special moments. Now I would be able to share the story of our proposal with our future children and grandchildren! I was so impressed that he had picked up on my hints and had tailored our proposal to incorporate my sentimental side.




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I became nervous as our walk down memory lane slowly came to a close, and we looked at the last photo that we had taken together over Christmas. Tim was holding my hand and smiling, and I knew what was coming! So I suggested that we sit down on the bench that was placed in front of a pretty little pond.


Tim began talking to me about our relationship and how much he had grown with me. He looked me right into my eyes and spoke beautifully and profoundly about our relationship. I couldn’t help but tear up, and neither could he. It was an intimate moment that I will never forget.

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Before I knew it, he was down on one knee with the most beautiful ring and was asking me to spend the rest of my life with him. I couldn’t seem to get any words out, so I just smiled and nodded eagerly. His hand trembled as he placed the ring on my finger. He mentioned that he was still waiting for that one word, and I proceeded to giggle and say, “Yes, yes, YES times a thousand!”

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christmas proposal

After the proposal, we held each other and savoured the moment. The proposal had been everything I had dreamt of and more. Jess, our photographer extraordinaire, watched from afar and captured the joyful celebration.



She then suggested that we take some engagement photos and we all went outside and bared the cold together. We walked around the pretty snow covered trees and took lots of photos.





When we finished taking photos, we said goodbye to Jess and got into Tim’s car. I was floating on cloud nine and then Tim mentioned that we were going to meet my parents to celebrate with them. It was yet another thoughtful gesture that included something near and dear to my heart— my family! I was thrilled!

We drove to a restaurant near the lake and Tim lead me upstairs to a more private area. As we walked towards the room, I noticed familiar faces and all of a sudden people were clapping and cheering and yelling, “SURPRISE!” Around 40 people were smiling back at us, and I was in complete shock. This was the icing on the cake. I noticed that Tim’s laptop was open and there were some of our friends and family who lived far away on webcam celebrating with us.



Most of my family and closest friends were in the room and I was so overwhelmed by their presence. Tim had out done himself and I could barely contain my excitement! I felt so blessed to have such supportive people rallying around us. The room was bursting at the seams with love and it was the perfect ending to the day that changed our lives forever.

Proposal Photographer: Jessica Rose Smith