Thank goodness for the internet because even though Jean and Jack are both Bay Area Natives, their paths might have never crossed! After Bumble brought these two together four years ago, and after a little convincing on Jack’s end, it seems as if these two were meant to be! Jean and Jack fell in love with each other’s adventurous sides, moving in together two years ago near Golden Gate Park where they are just a quick hop skip and a jump away from so many activities! They love exploring on bikes, going on hikes, and Jean is an amazing runner! They also feel so lucky to have so many close friends locally, that it’s hard to pass up a drink or dinner with friends! It was perfect that Jack chose to propose on a hike that overlooked the city, their home!
A week before the proposal, Jean’s sister Kirsten reached out to me asking if I could capture Jack and Jean’s proposal! We didn’t have many details, but I quickly got in touch with Jack and we got to work planning! He picked the Slacker Hill hike which was going to take them about an hour from start to finish. Lucky for me, there was an entrance to the trail 10 minutes from the top, so I didn’t have to hike the entire hour before with them. Jack and I spent the week sending pictures of previous proposals there that we had found on the internet, as well as google maps satellite images where I had drawn stick figures helping guide him on where to drop down to one knee. Since the proposal was in the morning, we had to battle the harsh light streaming straight on us, so it was important we found a spot that allowed us to see the bridge in the background, but also making sure that they weren’t blown out by any hot spots on sunlight. This entire week that Jack had been texting me, he had continued to fool Jean on his end. He labeled my contact as one of his best friends, simply just spelling my name with one letter off so he could tell the difference. After the fact when we asked Jean if she knew, she said that was really tricky because of course there wouldn’t be any suspicion if he was texting his best friend all the time!
Saturday morning, we all set off on our hikes, Jean and Jack from the bottom, and myself from the top parking lot. When I hiked up to the top, I was probably more nervous than Jack because what we couldn’t tell from the pictures was there was literally no where for me to hide. By the time you hike to the top of Slacker Hill, you are standing on the top of a flat mountain top, with the entire view in site. I got very lucky because it was fleet week, and people were slowly starting to show up to enjoy the view of the Blue Angels from above the bridge. I made friends with Mike, a photographer, and he even let me practice photographing him in the spot where Jack was instructed to bring Jean.
When Jean and Jack came up the hill, Mike and I looked at each other with smiles and kept talking. Mike was the ultimate decoy because he was there to photograph the Blue Angles, so naturally I fit right in! Once Jack got Jean in position, he asked her to turn around so he could take a cool picture of her facing the bridge, and by the time she turned around, he was down on one knee, ring in hand. Jean ran over to Jack, gave him a kiss, and exclaimed YES!
The surprises kept coming throughout the day, as Jean realized she knew who I was! I went to high school with Jean and Kirsten, and she was so surprised to see that I was their photographer! Jean, Jack, and I had the chance to keep chatting and it was so fun to get to hear the entire plan from Jack’s and Jean’s side…what she knew and what she didn’t knew. Jack did a really good job at keeping her in the dark. The proposal had been the most exciting part up until this point, BUT Jean didn’t know that there was one more huge surprise waiting for her in the afternoon. Jack had planned a brunch with their families to celebrate the engagement, and Jean still didn’t know that her sister, Kirsten, had flown out from the East Coast to celebrate with her!