• HOME
  • About
  • GALLERIES
    • PROPOSAL
    • ENGAGEMENT
    • WEDDING
    • Family & Maternity
    • BOUDOIR
    • PERSONAL BRAND
    • STYLED SHOOT
  • BLOG
  • INFO
    • KIND WORDS
    • FEATURED!
    • FAQ
  • Pricing
  • CONTACT

Olive Photography

Toronto wedding & lifestyle photography

  • Email
  • Facebook
  • Instagram
  • Twitter
  • HOME
  • About
  • GALLERIES
    • PROPOSAL
    • ENGAGEMENT
    • WEDDING
    • Family & Maternity
    • BOUDOIR
    • PERSONAL BRAND
    • STYLED SHOOT
  • BLOG
  • INFO
    • KIND WORDS
    • FEATURED!
    • FAQ
  • Pricing
  • CONTACT

Surprise Toronto Proposal Photography | Rob & Jeannie

January 28, 2018

Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop
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!)

—
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!

Surprise Toronto Proposal | Olive Photography Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop
Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel RooftopSurprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Skyline Proposal Photographer | Olive Photography on Thompson Hotel Rooftop Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography Surprise Toronto Proposal Photographer | Olive Photography

Categories - Blog, Engagement, Featured - Main Page, Proposal, Proposal - Featured Tagged - proposal, proposal ideas, Toronto proposal photographer, Toronto proposal photography, Toronto skyline proposal

Comments

  1. Shoko says

    January 30, 2018 at 3:28 pm

    BEAUTIFUL PHOTOS! Such an adorable proposal. The ring and the view are both gorgeous!! Way to go Rob!!

SEARCH

FOLLOW ALONG

  • Email
  • Facebook
  • Instagram
  • Twitter

CATEGORIES

RECENT POSTS

Airship37 Wedding Toronto | Olive Photography

Modern Airship37 Wedding | Amanda & Markus

Embracing Authenticity: Warm & Relaxed Brand Portraits in Toronto/GTA

Lifestyle Corporate Photographer | Olive Photography

Working from Home: Lifestyle Corporate Portrait Photography | Huumans

Toronto Proposal Photographer | Olive Photography

Toronto Skyline Proposal | Alex & Sydney

ARCHIVES

© Olive Photography | Toronto & Everywhere | info@olivephotography.ca | 416-520-1093

Copyright © 2025 · Everett Mae Child Theme on Genesis Framework · WordPress · Log in