For three months, Alex and I have been planning his surprise Toronto Music Garden proposal. Alex and Dylan are a couple from Boston who decided to visit Toronto for a short trip last fall. During their stay at One King West Hotel and while exploring the city’s famous attractions, Alex wanted to surprise Dylan with a marriage proposal.

Planning something like this from afar is always challenging. Finding the right photographer to capture such a special moment can be even more difficult. When Alex reached out for a quote and assistance, I knew I had to do everything I could to help make their moment perfect.

How We Did This Surprise Toronto Music Garden Proposal

Before their visit to Toronto, I had a couple of phone conversations with Alex. He wanted to make sure I was the right fit for his big proposal, and I wanted to fully understand his vision. I asked a ton of questions—not to overwhelm him, but to really get a sense of what he had in mind so I could offer the best suggestions for pulling off the perfect surprise.

One of the most important parts was pinpointing where we would meet and where he would get down on his knee to propose. Since I’ve worked in that area of Toronto before, I had a few ideas. Since they were staying at One King Hotel, I suggested the Toronto Music Garden as the ideal spot.

Alex was looking for something uniquely Toronto, and the Music Garden not only gave us the best view of the CN Tower but also had a beautiful setting that felt special. Timing was key, too. At 2 p.m. in October, the sunlight would hit the gazebo just right, giving us that perfect blue sky for photos. Of course, that all depended on whether the weather cooperated and the garden was not too crowded.

What it Takes to Plan Surprise Marriage Proposal

The plan Alex and I came up with was simple but thoughtful. After he popped the question, we’d take some photos in the garden and then stroll along the lake, stopping at HTO Park and Harbourfront Centre before wrapping up the shoot at Harbour Square Park. From there, they had scheduled a couple’s massage and a nice intimate dinner for the two of them.

With everything mapped out, we just had to wait for the big day. As with any outdoor fall photo session, many things could throw us off track—weather, crowds, or timing. But since I knew the area well, I was prepared for any curveballs.

I arrived at the Toronto Music Garden 30 minutes early to scout for the best photo spots and mentally rehearse how everything might unfold once Alex and Dylan arrived. The weather couldn’t have been more perfect—sunny and warm for an October day. A few people were milling around the pavilion, which gave me a chance to practice and picture how this Toronto Music Garden proposal would go.

To keep the surprise intact, I asked a woman sitting on the stairs near the gazebo if I could pretend to be taking her photo when Alex and Dylan showed up so it wouldn’t look suspicious. Thankfully, she agreed, and with that final detail in place, I was ready for the surprise proposal.

The Surprise Toronto Music Garden Proposal

As Alex and Dylan walked toward me, Alex sent a quick text describing what they were wearing since I hadn’t met them in person yet.
I saw two bubbly guys talking and walking towards the pavilion. I recognized the description and started focusing on their arrival.

Alex stopped earlier than we had planned, standing under the gazebo where the light was far from ideal. But without missing a beat, he pulled out the ring box. I rushed over, not wanting to miss the moment, adjusting my three cameras to ensure everything was set to capture the scene.

Once he took the ring, I could see the joy and surprise on Dylan’s face while Alex was getting on his knee. In these moments, I always cover the emotion instead of the scenery. The feelings can’t be replayed, and the scenery can be photographed once their little moment has finished.

After a minute or two, Dylan noticed me, and they shyly walked over. I introduced myself and congratulated them both. With the stress of the surprise behind them, we started taking photos around the Toronto Music Garden, making sure to include the CN Tower in the background.

Until today, I have not seen better weather for a surprise proposal, considering that October in Canada can be very unpredictable and rainy.

The Contusions Photo Session Alongside Lake Ontario

The boardwalk was pack with people enjoying the last day of October and the beautiful weather. As we made our way toward Harbourfront Centre, we stopped at several spots that showcased unique views of the city, giving a true sense of Toronto’s character.

We sat on the famous Muskoka chairs at HTO beach, which had a fantastic view of the Rogers Centre and the CN Tower in the background.
Afterwards, I took one of my favourite photos of that day at the Harbourfront Canoe place. I noticed a vibrant stack of canoes, likely pulled from the water for the season, and their bright colours reminded me of a rainbow—a perfect symbol of Toronto’s support for same-sex marriage. It felt like the ideal backdrop for Alex and Dylan’s proposal photos.

After capturing that moment, we moved to the Rees Wave Deck, where I took another favourite photo of the couple sitting on a bench. Here, I saw the real personalities of these two and their happiness in being together.
To add a personal touch, I snapped a close-up shot of their engagement rings resting on a vibrant maple leaf, symbolizing Canada.

With the photos done, I congratulated them once more and let them head off to enjoy the rest of their day, including a romantic dinner they had planned.

The Images Delivered The Very Next Day

I knew Alex and Dylan would want to share the exciting news with their friends and family in Boston as soon as possible. So I set a goal to deliver all 300+ photos the very next day. With so many candid and heartfelt moments captured during their Toronto Music Garden proposal, I managed to edit and finalize everything as planned.

Alex’s joy of getting their photos the very next day was indescribable.
The whole experience—from planning to execution and delivering the final results—came together perfectly, just as Alex had envisioned.

I’m thrilled I could provide them with beautiful photos, a memorable experience, and the warm, welcoming hospitality that Toronto and Canada are known for, especially for same-sex couples.

Thank you, Alex and Dylan, for trusting me to capture your special day.

Additional information for couples that like to see more surprise proposals and intimate same-sex weddings.

Check The intimate and heartfelt wedding of Sebastian and Federico at Edgewater Manor. View our post Sheldon Lookout proposal with Jose and Jessica for some inspiration for your surprise proposal.