Toronto skyline proposal Archives

Toronto Skyline Proposal | Alex & Sydney

February 6, 2024

Toronto Skyline Proposal Photography – A little different than the usual CN Tower skyline, it’s a lovely above-city East End view that is in a tucked away location after a short nature walk that makes this spot feel extra romantic and special.

This Evergreen Brickworks Proposal was such a sweet one. And gosh dangit, was it ever a beautiful morning!! Get a load of that gorgeous sunrise glow.

Alex chose to take these photos at sunrise to minimize potential for other people in the photos – it also tends to be a popular spot for photos with the skyline view behind, so the goal was to get ahead of any others who would come that day for a chance at the spot.

The Big Event – How it Went Down!:
Alex planned to take Sydney for a walk where they had their first date, a trail by Evergreen Brickworks, under the pretence of taking brand photos for their trampoline exercise company, Jump n’ Jacked. (How cool and fun does that sound?)I was hanging around, seemingly just a random person taking photos of the nature and skyline. When they arrived with a couple of friends who started to take cell phone photos of them, I offered to take a few photos of them as well that I could send to them since I happened to have a camera.
Little did Sydney know I was hired by Alex in advance as their proposal photographer!
We got a few snaps of them just posing (like ‘About Us’ bio photos), but very soon the poses for the photos changed quite a bit – Alex got on one knee and Sydney’s face was absolutely priceless. I got to capture the special moment and her happy tear-full reaction in all its beautiful glory – so much love!! Just have a look through the photos – her emotion was so beautiful. And they way they embraced and looked at each other.. *sigh* it warms my heart reliving it. I freaking love photographing proposals!

Toronto Proposal Photographer | Olive Photography

Big congratulations to Alex & Sydney on their engagement!If you’re looking for a Toronto Proposal Photographer, I’m your gal!!

Feel free to also check out some other proposal photos at this same spot, different season!

Hotel X Toronto Proposal | Neysha & Lucky

June 2, 2020

Hotel X Toronto Proposal | Toronto Proposal Ideas | Neysha & Lucky

Lucky wanted to bring tropical vibes to his Toronto proposal for the love of his life Neysha.
He also wanted to incorporate Toronto somehow, while also being weather proof.
He enlisted the help of Toronto wedding planner Carmen Luk of Devoted to You, and they decided Hotel X was the perfect location for the occasion since it has a rentable private multi-purpose room that has a gorgeous Toronto skyline view!
The room is tucked away behind a restaurant – totally unexpected and private. (Could even be rented for private dinners with the stunning view! How cool is that??)

Together with the help of Denovo Floral they put together a jaw-dropping scene that surprised Neysha when she thought she was going to a simple dinner that evening. The decor featured a unique swing centrepiece where the ring awaited Neysha as she walked into the room, and following the Big Question a little decorated table with bubbly awaited them to celebrate. So many thoughtful touches!

Lucky went the extra mile and even arranged to have some of Neysha’s closest local loved ones be there as part of the occasion. The emotions on their face were priceless – from giddiness and glee to emotional tears, I loved every moment of photographing this special time!

Hotel X was such a perfect location for this proposal! It has it all: an unobstructed skyline view, even more views of Toronto’s waterfront, gorgeous light from the floor to ceiling windows, interesting spots for photos at the hotel, AND a park with green space and waterfront just across the street for more portraits for after the proposal.

It was so much fun to be a part of this special occasion!
All the best to these lovebirds in their life together!!

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Enjoyed this Toronto proposal photography? You may enjoy Andy & Viv’s on Ward’s Island or Rob & Jeannie’s at the Thompson Hotel!

Surprise Toronto Proposal Photography | Rob & Jeannie

January 28, 2018

Surprise Toronto Proposal Photography

I’ve had butterflies in my stomach all week about this one! Such an exciting thing to be a part of!

Rob reached out before he moved to Toronto for a job assignment.
He and Jeannie are from Michigan and they’ve been together for 4 years.
His plan was to move to his new apartment in #thesix, then once settled have Jeannie come for a visit and surprise her with more than his new digs.

He wanted to find a place that really showcased what Toronto looks like.
What better way than to get a Batman/birds-eye view from above?

The folks at the Thompson Hotel graciously welcomed us to use the rooftop, which is usually closed during the Winter months. (It included a minimum spend in the rooftop lounge, but that made for a really nice way to round out the evening – They had bubbly and food ready for them as soon as we came back in inside!)

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She actually had a feeling he’d propose to her that day, but she thought it would be back at his apartment. He told her to get dressed up for a night on the town and her Spidey sense started tingling. Where would he do it? Would it be at a restaurant? She didn’t realize it would be something as epic as being on top of the city!

Rob and I kept a close eye on the weather. It was calling for rain, but we stuck to the plan and though cloudy, the rain stopped for the big moment!

When they came up to the rooftop to take in the view, her expressions as she realized what was happening were AMAZING. “Is this really happening??” She asked. He said he loves her so much and wants to spend the rest of their life together. When he asked the question, her response was a resounding, ‘DUH!!’ – It was adorable.

She kept looking at her ring, then back at him: “This is actually happening! We’re engaged!”
He revealed that he’d had the ring for 2 months. He had it custom made after a visit to a jewellery store where he took note of her preferences and ring size. Smooth moves, Rob!

Jeannie mentioned she kind of blacked out as it was happening. That’s not the first time I’ve heard of that happening at a proposal! Which makes it even more gratifying that I could be there to immortalize these memories for them.

Here’s a look at Rob & Jeannie’s surprise Toronto proposal!