The Chief Hike Surprise Proposal, Squamish BC - Jennifer + Jessica

One of the only times I’ll gladly hike a mountain is for any of my amazing clients, so it was no different when Jennifer planned to propose to Jessica on August long weekend. I don’t know what I did for the universe to bring Jennifer to me, but I am so thankful for my job and how it connects me to the most wonderful people. Jenn and Jess are someof the sweetest people and I couldn’t think of two people who are more deserving of each other! I’m so excited to share their story here, though it’s already been featured on a few blogs, such as Dancing with Her, Love Inc. and How They Asked! I’ll let Jess take it from here to tell you all how the proposal went down!


“On August 6 — the day after pride and the day before my birthday — Jenn took me to climb the Chief, a difficult hike in Squamish, as it was the first hike we did together the year before,” Jessica says. They had been together for nearly two years, and Jennifer had an entire day of surprises in store for Jessica that began with a video she had made. “The video included clips of my best friends from back in Ontario and Jenn’s family,” Jessica says. “In each clip, people discussed love, our relationship and then they all ended by saying: ‘keep climbing!’ By this point, I was a mess with tears quickly falling down my face, and we still had an entire mountain to climb. As they worked their way up the mountain, Jessica’s best friend popped out from behind a tree with a note for her to read. “As we walked on, another best friend popped out and then another and another,” Jessica says. “It’s safe to say our two-person hike expanded rapidly.”

When they finally reached the top, Jessica’s mom, dad, siblings and cousins were waiting for her, and Jennifer announced she had one more surprise. “She took my hand and led me to a quiet spot on the picturesque mountaintop right in front of a picture frame I had made for Jenn a couple of months prior,” Jessica says. Then Jennifer got down on one knee and asked Jessica to be her wife. Jessica couldn’t wait to say yes, as she’d been thinking about it since the very beginning of their hike. “I had a hunch from the bottom of the mountain it was happening,” Jessica says. “The moment she took out that video and I heard the messages, I just knew, and honestly, there was this feeling of completeness in my body. During the hike, I felt excited, nervous (in the best way possible), unbelievable happy and just overall grateful for this incredible human being.”