A couple weeks ago, my buddy Judson asked if I'd be willing to "stealthily take some photos" of him proposing to his amazing partner, Katie. I immediately told him how I stoked I was for them, but I'm not even close to a professional photographer and didn't wanna fuck up capturing their moment. He said it'd be super casual, in a remote park, and just wanted a couple mementos, so I agreed to scout it out with him. His goal was to get a "down on a knee popping the question under a light from a distance" sort of look.

The Recon

Judson told Katie that he was going to meet me for happy hour... but instead, we met at the park after work to figure out a game plan. It was my first time visiting this park, which was effectively closed for the season. As such, all the lights were turned off… and the sun had set a half hour earlier, so it was pitch black. There was no way the lighting was gonna be right for a photo at this hour. But, it was a special spot for them, so we walked through the park, and talked through his ideas.

He wanted to propose while walking their dog, Gus around the loop. When they were on the trail, I'd sneak in, hide behind a tree, and wait for them to come back around. Once they got to this curve in the road that he’d picked out, he'd pop the question and I'd take the shots. It seemed like it'd work as long as the lighting was right, so we set a date and agreed to shoot for sunset.

The Second Recon

I didn't wanna do this without some test shots, so I took Kari and Durby back out to the park before sunset. I pointed out the tree that I'd be hiding behind and where Judson would propose... It looked so different in the daylight, but I’m certain I had the spots right.

I tried a couple lenses and positions to get the best framing, made some adjustments, and got some test shots that I was happy with. Kari, however pointed out that I stuck out like a sore thumb next to the tree. It didn't help that I was wearing a hi vis orange hat... but it made me think that I should probably wear camo and be extra careful about not blowing my cover.

I felt a little better after getting the camera dialed in.

The Final Game Plan

First, Judson and I shared live locations with each other on our phones.

They would arrive at 4:15 and take Gus for a walk - off-leash. I'd track his realtime location and as soon as they were out of sight, I'd pull up, get to my spot and get set up. Once ready, I'd text Judson and they’d make their way toward the proposal spot.

My main concerns at this point were:

Getting seen by a stranger and blowing my cover by looking like a weirdo, creeper
Getting spotted / sniffed out by Gus, who'd be tromping around off-leash
Getting spotted by Katie
Popping out at the wrong time and messing up their moment

Given my position, we didn’t have a good way for me to know when to pop the shots without blowing my cover. I could semi-accurately track their location but needed an audio cue... so, Judson was going to call for Gus when the time was right. As soon as I heard that, I'd wait a couple beats and then pop out to grab a bunch of shots of the proposal.

It was a reasonable plan.
Mildly stressful, but a fun challenge.

The Mission

The night before the proposal, I dreamt and thought about all the ways that I could mess this up... and it wasn't even my proposal! My Apple watch gave me a sleep score of 3 out of 20 for the amount of interruptions, tossing, and turning that I did, haha.

I was asked to capture such a special moment for a great couple and I really, really wanted to nail it for them.

That morning, I laid out my camo, made sure my SD card had space, my batteries were charged, and my camera had all the right settings... Aperture and shutter speed were dialed in, Autofocus mode was right, facial recognition was on, and the capture speed was on blast.

Late afternoon, I suited up, got the word from Judson and we both headed toward the park.

I was tracking his location and it looked like we were going to arrive at the same time, so I hid out in a nearby cemetery to give them space (and tie my boots... forgot to do that). As soon as I saw them moving along, I slowly drove up in my Bronco, parked and closed my door as quietly as possible. Then, I realized that I needed my camera, so I opened the door back up, grabbed my camera and closed the door as quietly as possible again. I, then made my way to the spot like a ninja, looking for signs of them, or anyone else along the horizon - but nothin. So far so good.

Once at my tree, I checked all my camera settings again, took a couple test shots, texted Judson that I was in position, and took a selfie.

While tracking their location on my phone, the high-accuracy pinpoint expanded to the larger, low-accuracy view and I no longer knew exactly where he was at on the trail. Shit. No worries though, they were close and he was going to call for Gus when the time was right.

I started to hear what sounded like talking/laughing... it certainly wasn't a call for Gus. Or was it? It was pretty windy and hard to hear over the wind and leaves. So just to be sure, I risked it and peeked out. They weren't in the spot that I was set up for. Double shit. So, I pivoted to the other side of the tree and tried to peek my head out without getting busted by Katie or Gus.

As it turns out, I missed the call for Gus because at that exact moment, Judson yelled, "Derek! Take the picture!" lololol. 🤦 So I popped out the back side of the tree, kind of off balance and fired off 20+ photos of a beautiful moment with a beautiful couple and their dog.

Judson on his knee, Katie's reaction, holding hands, kisses. It was awesome.

But the one thing that I didn't even notice and hadn't accounted for was that, from this angle there was a tree stump directly in between us. And that stump had a handful of sprouts or sticks growing out of it.

My camera locked its focus on those sticks for 19 of my 20 shots… but it all happened so fast that I didn't even notice. It looked like we got the shots, but with my distance and the aperture I was shooting at, Judson and Katie are completely out of focus and bokeh'd in what would have been the money shots.

So... I was able to get them some "mementos." They're certainly not the mementos that I'm guessing they'd hoped for, but they're kind of funny, I guess? Maybe artsy?

We really should've mic'd Judson up, set out a video camera or a mirror that I could monitor... or thrown out a visual marker exactly where we planned to take the photos so Judson knew where to stop. I definitely should've noted or eliminated anything in the vicinity that might've given us any kind of interference in the shot. I should've reviewed the photos more closely immediately after shooting. And most importantly, I should've used this as an excuse to buy a full ghillie suit for me and my camera. So many "should haves" that I keep thinking of.

So, that's a little story about how I fucked up my buddy's proposal pics and why I'm not a professional photographer.

I'm both so happy for Judson and Katie and also kinda feel like an idiot. They're a great couple, and I'm glad that I got to play a small role in fucking up the documentation of their special moment, hahah... Don't ever hire me for something that you care about.

At least Judson nailed his part.

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