Yes, you read that right. My fiancé Jon tricked me into planning my own proposal. If you know me, you know I’m the type of person who likes to be in the know. So, when Jon and I were talking about getting engaged, we both knew he would have trouble surprising me. Especially since I caught him, on multiple occasions, talking to “Curtis” on his phone, who I quickly deduced was actually our jeweler Lena of KV Jewellery.
So how did he trick me into planning my own proposal? It was a very elaborate plan, and one that I was actually very impressed with…
How It All Started
At the beginning of August 2017, our good friends Josh and Christina aka Jay & Cee Photography (wedding photographers extraordinaire) messaged us about going on a hike, a double date activity we had talked about for awhile. Unfortunately, I had already made plans the one day that worked for them: August 27, 2017. Funnily enough, the plans were with my Stone & Fern co-founder Kitty!
On August 14, Kitty canceled her plans with me citing that she would be too hungover from the night before. I didn’t know at the time, but Jon had asked her to and let her know he was planning on proposing!
I quickly relayed the news to our friends and August 27 was back on!
The next day, we had half-priced wings with our other dear friends Natalie & Yutat, who were expecting their first child. They mentioned how they’ve been trying to schedule an outdoor pregnancy shoot with Jay & Cee Photography. And I decided to invite them along on our hike, saying we’d love to help assist with their shoot – they excitedly accepted my invitation. Unbeknownst to myself, I was slowly ticking off Jon’s engagement checklist.
1. Make outdoor plans for August 27
2. Ensure photographers are there
3. Give the photographers an unsuspicious reason to have their cameras
Josh & Christina suggested Belfountain Conservation Area, a park an hour away from Toronto, claiming that they’ve been meaning to visit. It was quickly decided that Nat & Yutat’s pregnancy shoot would take place there!
August 26 was the day of a friend’s wedding (another Nat), and a happy reunion as many out-of-town guests flew in. More people were invited to join us at the shoot! Little did I know, everyone was in on the proposal and Jon had riskily overshared to several guests at the wedding…
The Big Day
Since we had quite a big group, we took 2 cars up to Belfountain. Jon and I carpooled with Nat and Yutat, who had brought a number of props including the cutest onesie stating, “Daddy’s Boss”. After arriving, we quickly met up with the other car; however, one of the couples were missing. When I asked about their absence, I was told that they had a bit of a disagreement and were talking it out. I totally believed it and didn’t ask more questions.
We spent about 30 minutes taking beautiful pictures of the expecting couple, slowly making our way into the middle of the park. During the shoot, I held onto Nat’s purse for her. What I didn’t know was that they were all quite nervous since the ring box was actually inside her purse! While they were taking pictures, Josh asked Jon and I to move onto the next area, scouting the next photo spot. I didn’t realize, but Nat had stealthily passed Jon the ring.
Jon and I made our way up a few steps onto a little path. As we walked, he noticed a book on the ground and pointed it out to me. I acknowledged it was there and tried to proceed walking, but he stopped me and said, “Maybe you should pick it up.” I immediately thought to myself “Why would I pick up a random book from the ground…” before realizing he was trying to propose!
It was a scrapbook filled with embarrassing pictures/Snapchat screenshots throughout the length of our (mostly long distance) relationship. By the second page, I was already tearing up and trying to flip through it as quickly as possible since I realized our friends were filming and taking pictures a short distance away. The last page asked the question and Jon went down on one knee. I (obviously) said yes, after jokingly saying no.
Side Notes
- After helping to plan this day, I was truly caught off guard by the fact that it was my own proposal. This was evident by my chipped nail polish and unwashed hair. Thankfully, I wasn’t in complete athleisure since it was supposed to be more of a photography shoot than a hike.
- Apparently some people do pick up random books they see on the ground. The “fighting” couple weren’t actually fighting, they were on scrapbook guarding duty. They witnessed a passerby pick up the scrapbook and had to tell them to please put it back down lol. Now I need to know, would you pick up a random book sitting on the path in front of you?
- Jon originally wanted to propose on the suspension bridge, but there were too many people on the bridge when we arrived. I’m glad he didn’t since we’ve all seen proposal fails where someone drops the ring!
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Stone & Fern is a travel and lifestyle blog started by friends who have a passion for exploring cities, capturing moments, and trying new food.