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Real Weddings

The Sweetest, Swoon-Worthy Proposal Stories

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Who doesn’t love a romantic engagement story? We count ourselves very fortunate at Weddingbells as we have the opportunity to read so many amazing and personal ones shared by our real wedding couples.

To celebrate Valentine Week, we wanted to share some of the love with you. Read on for some wonderful and romantic proposal stories we guarantee will deliver all the feel-good vibes we all need now.

Nicole & Sean (pictured)
From Nicole: “Sean and I got engaged in Kauai, Hawaii. I was getting close to finishing my PhD, but was not quite there yet, so I did not expect it to happen when it did. On one of our first days there, we went for a five-hour exploration adventure, which included crossing through rivers and lots of climbing and this is where Sean wanted to propose. That did not end up working out as planned as he had left the ring back where we were staying. That evening, we had a beautiful dinner reservation, but ended up cancelling it because we were pretty exhausted after our hike! We decided to drive out to Poipu Beach later on because I had heard about the sea turtles that come up onto the shore in the evenings. We ended up at the beach and we stood in awe of the amazing, majestic sea turtles that were on the shore in front of us. Just as I looked back at Sean he said ‘I have something for you. Do you know what it is?’. It was so special. We even had sea turtles added to the top of our cake on our wedding day as a nod to our engagement and the beautiful setting in Hawaii.”

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Samantha & Stefano
From Samantha: “This is an interesting story! We decided to move in together before we got married, so the day we got the keys to our house Stefano proposed to me. He received the keys to our house the day before to set up a sign and flowers everywhere. His dad actually recorded the whole thing and I ugly-cried SOOO hard. I actually posted the video to Instagram and the next day, the video was literally popping up everyone on so many accounts. It was nuts!”

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Jonathon and Kayla
From Kayla: “We took a summer trip to Rwanda where Jonathon is from and made the trip to visit is extended family and show me the country. After a week of family activities we toured around on our own visted Akagera National Park, a safari park in Rwanda. The safari tour was a full day tour that began at 5 am. Jonathan had my engagement ring but with no precise plan on how to do the proposal, but he had a couple of possible ideas that might make it extra special in his home country. One of his possible ideas was during the safari if there was a place for great pictures. At the beginning of the safari tour, Jonathan asked the guide if there were places where everyone could get out of the truck to take pictures with the animals in the background. A few hours into the safari they made it to a picnic area where giraffes and zebras were walking around. They got out to take pictures and Jonathan quickly realized this was the spot! No one was aware of what was about to happen except for his sister and his best friend. Jonathan told his friends to take a video of us with the giraffes. Jonathan pretended like they were just taking another picture and before I realized it, Jonathan was down on one knee asking me to marry him.

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Jennafer & Craig
From Jennafer: “Craig woke me up early on a Saturday morning to take me for brunch at my favourite spot in Fort Langley. Fort Langley has been a popular date destination for us as a couple and is one of my favourite places. Instead of parking close to Wendel’s Bookstore and Café, he drove across the bridge to the park. As we were walking over the Jacob Haldi Bridge to our brunch spot, he stopped halfway over the bridge to give me a present. He said he wanted to surprise me for working so hard on my recent Internal Medicine rotation during my Residency. I opened up the present and inside was a stethoscope. He told me to look closer at the inscription, and on the stethoscope was my first name with his last name. Then I looked at him and he was on one knee with the ring in his left hand. He told me that I was the most amazing person that he had ever met and then asked, ‘will you make me the happiest man on earth and marry me.’”

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Simon & Jasmine
From Jasmine: “I always told Simon that I didn’t need a ‘big’ proposal—all I wanted was to be with family and friends during an evening where we were all together for dinner or something. And, as most couples do before they get married—or at least the women —discuss what the engagement ring is going to look like! Every time I talked about it, Simon would say ‘the more you ask/talk about it, the longer it’s going to take!’ Well, that wasn’t so true, because I talked about it a lot and remember having a conversation with my mom and Simon about what the ‘hypothetical’ proposal/ring would be like, just the week before it happened. So, fast-forward a week later to Simon and I throwing a house-warming party as we just bought a new home and invited family and some close friends. At one point throughout the evening, Simon wanted us to do a little speech and thank everyone for coming, and guess what!? He PROPOSED! At first, I thought I was dreaming, and then I asked him if he was serious AND then I said yes! It was such a surreal moment.”

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Yvonne & Steve
From Yvonne: “We had been together for almost eight years when Steve proposed to me. We drove to my favorite restaurant (we got there before the opening hours, so there is no one in the restaurant except one waiter). When I sat down, he got down on one knee and said the most wonderful and romantic thing, I was so surprised and said ‘YES!’ Later on, he told me how he had been planning everything like talking to the restaurant to open early for us and having a hidden photographer on site to capture all the moments!”

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Stephanie & Stephen
From Stephen:I always envisioned proposing to Stephanie at the Christmas Market at The Distillery District in Toronto. It was something that became a tradition of sorts for us to attend year after year together during our relationship, and I felt it was a special place for us. As Christmas was approaching, the days left to attend the market began to dwindle, so she found it odd I was so insistent on going down on the second to last date it was opened for the year. She thought I was acting weird since I was a little on edge, and when we finally got into the market after enduring what felt like a never-ending line, I was constantly on my phone texting the photographer from 5ive15ifteen I had arranged to capture the moment. Stephanie started figuring something was up when I insisted on taking a carrousel ride and that we needed to take a picture amongst the crowd by the giant Christmas tree. As we strode away from that selfie by the tree, and got deeper into the market, I felt the crowd around us disappear, and decided to go for it, and get down on one knee and. Although she barely heard the speech I had rehearsed in my head a dozen or so times on the drive down, she knew what was happening as soon as she locked eyes with me and noticed I was on one knee, holding her hand and trying to fumble open the box. It didn’t happen like in the movies, where the whole world stops and cheers, when it’s over, but for me, for that minute, it was just Stephanie and I, amidst a crown of thousands.”

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Nadia & Lihn
From Nadia: “Lihn proposed to me on our 15th anniversary. We celebrated with a long weekend trip to Quebec City and Lihn proposed during a horse and carriage ride. We planned our wedding for a year later and it was such a huge step for us in our love story. We had bought a house together and had a child but it took us 15 years to get married. I will say the moment before walking down the aisle was very special for us—the event became so real and our emotions were running wild!”

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Jacqueline & Scott
From Jacqueline: One summer Saturday, Scott lured me onto a yacht under the pretense of last-minute client cancellations and a complimentary tour of Lake Ontario. I fell for it entirely and it wasn’t until the boat turned back to the harbour that I turned around and saw Scott get down on one knee. After lots of “yeses” and kisses, we then came back to port where our friends were waiting with champagne and we sailed the evening away as the sun went down.”

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Melissa & Scott
From Scott: “The proposal was a little nerve racking for me, I had my Nana’s family heirloom ring in my possession for about two months before I asked Mel to marry me. We had a very cute room booked at the June Motel in Prince Edward County, and I figured I would do it there. As we were eating a Charcuterie board in the Motel room and having some wine, I got down on one knee at the end of the bed and asked her if she would marry me. She started to cry a little bit and said, ‘Is this for real?’, and I said yes, and she said YES. We had reservations at The Drake Devonshire which was so fitting because we met in front of the Drake hotel in Toronto. The rest of the weekend felt like an absolute dream.”

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