Toronto Rooftop Surprise Proposal

Emaleigh and Michael met at a costume party that was set up as their blind date by their best friends. Everyone was assigned a costume that matched one other person at the party. Of course, it was arranged that Emaleigh and Michael would match. When they both showed up wearing nurse’s scrubs they started getting to know each other. The two of them had such an instant connection that they actually became a couple that very day. It’s been 5.5 years since they’ve become completely inseparable. I first met Emaleigh working at the same camping store. It had been years since I’d seen her but we set up an adventure session to create photos with her boyfriend Michael. The photos we created that day are some of my all-time favourite. Their love radiates so clearly that all it felt like I had to do was sit back and let them be as they are. At that shoot, I learned that Michael was planning to propose on their summer trip to Switzerland.

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Well, you know what happened so that was no longer possible. A few weeks after our first shoot I received a message from Michael saying that he had replanned his proposal and wanted me to capture it. I was sooo excited to be creating again with them, especially that it’s such a big moment in their relationship. Michael planned an incredible moment on the rooftop of his workplace located in the heart of Toronto. The views were jaw-dropping. While they walked up I hid for a moment behind the railing. When I popped up and started shooting Emaleigh knew right away what was about to happen. That’s when the tears and smiles started exploding outwards. By the time Michael asked the question he was crying tears of joy as well. It’s being a part of moments like this that make my heart full of happiness.

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Toronto rooftop surprise proposal by Toronto proposal photographer, Chelsey Cunningham