Canadian Celebrities And Influencers Share Their Romantic Proposals

  |   By Alison McGill
Photo by Annie McElwain courtesy of Jessi Cruickshank.

For Valentine’s Day we asked 11 famous friends to share their magical proposal moments with us. We found out Jessi Cruickshank said yes to her husband Evan on Christmas day in front of her entire family. The Style Guys' Aly Velji was surprised with an incredible sunset proposal in  Santorini by husband Jason. Everyone loves romance, and all the engagement stories that follow are the most fun, funny and fabulous moments.

Photo by Annie McElwain courtesy of Jessi Cruickshank.

"My husband and I went on our first date in 2006, at a little restaurant in the lower east side of Manhattan. Six years later, he made elaborate plans to propose to me just before Christmas, at that very same little restaurant. He had the ring, the reservation, the permission from my parents and the plan to meet me in New York City after I wrapped shooting in Toronto. He was ready. Except the day before… I cancelled. ‘I’m swamped at work honey, I’m so sorry—can we just skip the New York trip and meet at my parents house for Christmas?’ Not wanting to spoil the surprise, he moved to plan B. A proposal on Christmas day, in front of my entire family. I was still completely oblivious and rolled out of bed in yellow polka dot pajamas, an oversized sweatshirt, and my hair in a messy side ponytail. ‘Don’t you want to change?’ he asked casually around noon, the ring burning a hole in his pocket. ‘Evan,’ I said ‘it’s CHRISTMAS. I am staying in my pajamas all day.’ ‘Maybe just… a shower?’ he implored. ‘Nope!’ I shrugged, wiping cookie crumbs onto my dirty sweater. He must REALLY love me because he proposed to me anyways. He said beautiful things, then got down on one knee in front of my clapping, weeping family. We hugged, we kissed, I said a euphoric YES and then…BUT WHY DIDN’T YOU TELL ME TO CHANGE!!!??”Jessi Cruickshank, television personality

Photo courtesy of Erica Wark.

“After 14 years of dating (we're high school sweethearts), Corey proposed to me LIVE on The Social during one of my segments! The date was July 11, 2014 and I was SHOOK. I had no idea he even had a ring! In fact, I didn't even know he was in Toronto that day (he works in Ottawa through the week). It was apparently planned for months without my knowledge. He walked out from backstage holding a rose, got down on one knee and popped the question. But what was even MORE special, is he also surprised me moments later with all of our friends and family who were hiding down the street at the Beverly Hotel rooftop. They all watched it on TV at the hotel while it was happening. My assistant was even in on it, pulling three outfits for me to choose from to wear for the celebration post-engagement! He planned a beautiful dinner with all of our closest loved ones, and even booked us a hotel room for the night. It was magical.”Erica Wark, celebrity stylist and fashion expert

Photo by Emma Brittenden as seen in this real wedding.

“We went away for a weekend in Prague, we were living in Frankfurt because that is where I was playing soccer. The day had a crazy start. We woke up early to catch a train into Prague which we almost missed. The city was spectacular. We wondered the city streets. Nic had done some research about the city prior to departure, as he usually does when visiting somewhere. The proposal happened in a hidden garden on the hillside below the castle We went searching for these secret gardens Nic had read about. Finally, we found them. Well worth the search, they were beautiful. As I was climbing up another set of stairs which was surrounded with flowering vines all around. I thought to myself, ‘this would be the perfect place to get proposed to, but he doesn’t have the ring yet so oh well.’ At the top of those stairs was a stunning lookout over the whole city of Prague. I naturally went crazy trying to take photos. Eventually as I calmed down and was taking in the view. From behind me I hear, ‘so there’s this..’ I turn around and he is down on one knee holding out the ring box with the perfect ring inside. The rest is a bit fuzzy because I was overwhelmed with emotion. I said yes, then had a little freak out. It was splendid. It was us and exactly how I wanted it. No one around. Nic did well!!!!”Sophie Schmidt, two-time Olympic Canadian soccer pro

Photo by Paul Wright featured as part of this real wedding.

 "Justin proposed on Halloween night 2016. I was TOTALLY surprised as I did not see it coming. Up until this point, Halloween was not a symbolic day for us, but it is now. I did not realize that Justin had secretly been working on my engagement ring for three months. He designed it himself and had it made out of gold that he had panned for in the Yukon several years before. I was surprised on many levels! The reason he decided to propose on Halloween night was because that was the day that the ring was ready and he is really bad at keeping secrets. He carved a question mark into a pumpkin which totally went over my head as I was not expecting a proposal at all. Now we carve a question mark into a pumpkin every year.”Sarah Keenleyside, HGTV Canada star

Photo via Instagram/@thetracymoore

"Lio and I started things by doing something my parents didn’t like—buying a house before getting married. My folks are a little old school so I explained Lio was absolutely THE ONE...he just wanted to get a leg up in the housing market sooner rather than later. And also, a mortgage amortized over 20 years may as well be a marriage, no? Once we committed our down payment we were left with approximately zero dollars to decorate. Much to my surprise Lio had been paying attention to my obsession with decorating shows. Without saying a word he contacted the producers of Debbie Travis’ Facelift and organized a surprise trip for an girlfriend and I to go to Montreal for three days. When I got back I walked into a reality show. This was the lead up to our engagement story (because who says no to marrying a guy who just snagged a $100,000 makeover for FREE?). Two days after the reveal he took me to Langdon Hall in Cambridge where the door-greeters immediately gave us champagne and congratulated us on our engagement (ummmm, he hadn’t asked me yet so I now knew IT WAS GOING TO HAPPEN HERE). We took a walk on one of the beautiful trails before dinner and when we were far enough away from the building he got down on one knee told me I’m all he’s ever wanted in life and asked me to marry him. We cried, we kissed, it was mushy and tender and beautiful. And I left Langdon Hall with the beautiful ring we had picked out together (hello...I’m still a Capricorn) as happy as can be. It’s the best decision I’ve ever made in my life."Tracy Moore, host of Cityline

Photo by Sydney Takeshta of London Light Photography as seen in this real wedding.

“Jason planned to propose four months before a big trip to Europe. It was all set up it would go down on their first night in Santorini. There was us and three other couples travelling together and only one of the couples knew it was happening. Reservations were made at a restaurant that overlooked the sunset and after meals were ordered we went down to take some photos together – that’s when it happened. He said yes! People who were walking by were congratulating us, crying, and the other restaurant guests (along with our travel-mates) were ecstatic.”Aly Velji, The Style Guys

gorgeous mountaintop wedding in boulder, colorado - liz trinnear and nathaniel motte Photo by Rebecca Amber Photography as seen in this real wedding

"Nathaniel and were on a trip to England and France the summer of 2016. We had just spent a wonderful week in London, and we flew down to the South West of France where Nathaniel’s mom is from, and where most of his extended family lives. Nat insisted we go straight from the airport to the summer house his grandfather built to see it before all the family got there for their vacation (his parents were also married there on 7/7/77). I had a coffee stain on my shirt, and no makeup on. I had absolutely no idea that he was going to propose. He brought me up to the balcony, (still no idea…) overlooking the bay, and popped the question (meanwhile I thought he was tying his shoe). I said, YESSSSSS!"—Liz Trinnear, LA correspondent for etalk

Photo courtesy of Cheryl Hickey.

 “I remember I was wearing yellow that day hosting ET Canada and feeling really excited about my date night with Kev. We were going to the Keg Mansion—I love a good baseball steak, mushroom caps and Caesar! We had an amazing dinner and were talking about going for a drink after dinner at 7 West where we had our very first blind date together where he wore a name tag that said “Hello my name is Kevin.” We arrived at 7 West and he started saying the sweetest things about our relationship and I was looking off at an apartment building wondering why the outside looked the way it did. I got distracted just for a moment then tuned in and he was down on one knee and snapped me back into reality and body literally froze. The I heard will you marry me. I said yes right away and smothered him!  He walked me around the corner to where a stretch limo was waiting and we drove around the city drinking champagne calling all our family and friends. It was so much fun!”Cheryl Hickey, host of Entertainment Tonight Canada

Photo courtesy of Bliss Katherine as seen in this real wedding.

“I custom designed Taylor’s ring with one of her favourite designers, Smith & Mara, in Los Angeles. I wanted to propose to to her in Toronto where we met and have so much history together, I waited until we went there for a show I was directing. On our way to Toronto I had to bring the ring in my carry on and I was so nervous security would ruin the surprise so I wrote a little note on the ring box that says ‘shh this is a engagement ring please be discreet.’ After the show wrapped I told Taylor I wanted to have a relaxing day to try and unwind. We went for brunch at our favorite old spot, Lil Baci, then for a massage, and then to Leslie Jones for dinner (where we went on one of our first dates). After dinner I kept persisting we walk a different route home, and Taylor kept persisting we stay on Queen Street. Finally, she agreed to go my route and she put her hands in his pockets for warmth as we walked. We got to a street corner and I said “Do you recognize where we are?” She looked around and noticed we were on the exact corner where we had our first kiss. Before Taylor could even figure out what was happening on this dimly lit street I was down on one knee. She was so shocked and then started laughing and crying and I said ‘You have to give me an answer!’ She said yes and then we hopped in a car and headed to the Park Hyatt rooftop (another one of our first date spots) to celebrate with champagne!—Gregory Smith, actor, director and star of Everwood and Rookie Blue

Photo by Tino Berardi for Sunwing Vacations. Sarah's makeup and hair by Rachel Renna and Ryan Dowell. Dress from Kleinfeld Hudson's Bay.

“Bryan and I were married September 3rd in Toronto at Graydon Hall Manor and this September will mark our 15th anniversary together! Our engagement happened in Nova Scotia. Bryan and I were living in Vancouver for the first few years of our relationship and had just returned home as we hadn’t spent much time together with our families. First stop was a trip to Nova Scotia where Bryan’s mum was born and raised. We spent a week visiting with extended family and friends—it was the first and last time I was able to meet his grandparents before they passed away.  On the last day of our trip Bryan planned a special outing to the very eastern tip of the island where the view of the ocean was said to be unparalleled. It was that afternoon that Bryan intended on asking for my hand in marriage, but unfortunately the weather turned and fog and snow flurries rolled in. Roads were closed down and as luck would have it, our car broke down. We were towed to the nearest mechanic shop where we sat for hours eating food from a vending machine. Although it was not the romantic day Bryan had planned, he did still proposed that night. The proposal was much more casual, over a bottle of wine and a hot bubble bath, and looking back now I think it truly set the stage for our life together; always changing, constantly evolving, and grounded in chaos!"Sarah Baeumler, HGTV Canada host, House of Bryan, Bryan Inc., Island of Bryan.

This article was originally published on Feb 13, 2020

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