This was the most stressful photoshoot of my life.
Joshua (right) reached out to me to shoot him proposing to his boyfriend Reuben (left). We met at Alloro Vineyard in Sherwood, Oregon. Joshua organized all of their closest friends under the ruse that they were celebrating Reuben’s sister. According to Joshua, it’s incredibly hard to sneak things by Reuben. So everything had to work out perfectly to avoid Reuben finding out what was actually happening.
Joshua told me that at exactly 2:25pm he was going to gather everyone in the small garden directly outside of the tasting room, give a small toast to Reuben’s sister and then give a small toast to him and propose. It seemed simple enough. I got there early, got my own glass of wine and blended in with the crowd so Reuben wouldn’t be suspicious at all.
At exactly 2:25pm about half of the group, including Joshua and Reuben, got up and walked away from the small garden and towards the actual vineyard. This is when the stress started.
I didn’t know what to do. I didn’t know if he was going to propose at a different spot. I didn’t know if they were just walking around for a bit. I was freaking out. This is not something you can miss as a photographer.
I grabbed my camera and did a big loop around the tasting room because I didn’t want anyone to see me. Joshua’s friends didn’t know he was proposing either so I tried to be as inconspicuous as possible (I found out later that literally everyone saw me and thought I was super strange). I eventually found Joshua and Reuben and the small group they were with in the back vineyard. I didn’t know if this was the moment or not so I hid behind a bush and waited, camera in hand, ready to jump out and start shooting like a madman.
I heard someone say, “Wow, what a nice view.” And then they all turned and starting walking back towards the garden. It turns out this was not the moment.
But now there I was standing alone behind a bush with a camera. I wanted to remain unknown so I hid my camera in the bush and pretended to be on the phone as they walked by.
Did I need to do all of that? Probably not. Did I do all of that? You better believe it.
About 10 minutes later Joshua gathers his friends and starts his toast to Reuben’s sister. I sigh a breath of relief with the knowledge that this is definitely the moment. I snuck around behind Joshua and Reuben, so I could capture the moment with all of their friends in the background.
As I’m setting up my shot I realize I need to be a few feet back in order to get their full bodies in frame. I turn around and there’s an older couple standing in the exact spot I need to. This is roughly 20 seconds before Joshua is going to propose. I whisper to the couple, in my quietest and most secretive voice possible, “Would you mind if I stood her for just 30 seconds?”
The old man responds, very loudly, “OH WHAT ARE YOU DOING THERE?? TAKING PHOTOS???”
My heart dropped. I thought Reuben was going to turn around, see me waiting with a camera, and the surprise was going to be ruined.
Luckily he was so enthralled with whatever Joshua was saying that he was blind to the rest of the world. Joshua got down on one knee, proposed, and thus began the rest of their lives.
This was by far the most stressful shoot I’ve ever had. Of course, most of that stress probably stems from my stupidity and personal overreactions. Either way, it ended up being a huge success and I could not be happier with how the photos came out.