Photographing My First Proposal

Love is in the air.

Word has gotten around that I recently photographed my first wedding. Enough so that I’ve been getting a myriad of requests to do photoshoots for other occasions. Family portraits here, headshots there, collage of a pet iguana, all of which I’m happy to do. However, those are fairly basic and require little emotional energy from me. Rule of thirds (or is it a suggestion?), correct exposure (or not for dramatic lighting?), remember to format the memory card (always a must), and away we go! Then my boss caught me in the hallway and asked if I’d be willing to do an engagement shoot for a friend of his.

Two things I’ve learned in my experience of corporate employment: 

1) When your boss asks if you are willing to do something, you should say yes. Unless, of course, it is unethical. Then contact your local HR rep…

2) Always remember to ask clarifying questions before agreeing to anything.

These two should be in reverse order. You see my mistake already. Let me break out my flow chart to demonstrate.

Ask questions before saying yes -> Say yes

A person thinking logically would have sorted this correctly. I was not thinking logically. Frankly, I was just excited that I was being asked to do more photoshoots. Needless to say, I’m enjoying the opportunity to expand my offerings and learn more about portrait photography.

Fortunately for me, the location of this engagement shoot was less than a mile from my office. As standard practice goes, I would typically meet with the couple to discuss the location and how / where they would like the photos taken. It gives me time to scout the area, see if there are any particularly nice spots, and get an idea of what kind of photos they would like. However, I found out that the fiancé was not going to be joining us on this initial meeting. 

That struck me as odd.

Not to be that guy, but in my experience, it is typically the ‘not guy’ that has more particular opinions of the photos of themselves. Dress code, lighting, poses, and entire Pinterest boards full of ideas and desires. Fairly common. We had none of that. I had a guy calling all the shots. Except I was technically the one doing the shooting…?

I wanted to have confidence that he was pointing me in the right direction. The last thing I want is to spend the time taking photos and editing them to his liking only to turn around and find that she would have been happier with an Instagram filter on a selfie. And in today's world, that is my competition.

Anyways, while waiting for this individual, my boss and I are scouting out the area. We stumbled across a really nice overlook of High Falls in Rochester, NY. Done. All of the photos would be taken here. I can do so many things in this one spot. My boss had offered to take photos with a drone which works well with the overlook. 

Then my boss's friend showed up.

Friendly gestures, strong handshake that mildly injured my trigger finger, and we chatted about the location. I went into my spiel about lighting, backdrops, and the type of lens I’d likely use. I even took a few shots to show him what it would look like. I’m nailing this engagement shoot, it’s like I’ve been doing this for years. Then I heard the most unexpected, derailing (there are train tracks nearby, you’re welcome), words come from his mouth. “And this is where I’m thinking I’ll propose to her.”

What.

Clarifying questions. They are really helpful. My definition of an engagement shoot was taking pictures of two human beings who are engaged. Apparently, this definition has been grossly rewritten to take pictures of two human beings in the process of getting engaged while being undercover as a landscape photographer. That was the plan all along. Poor, little, old, naive me. 

The good news is, I can do that. I’ve played the role of an undercover landscape photographer for years now. So much so that people still don’t know about it! I’d like to say that I took this comment in stride. No one would have known that this was coming as a complete surprise. We just went from believing that this would be an engagement shoot to now seeing the reality of the situation. This would be a proposal shoot. My first ever proposal shoot.

But there was still something missing.

Our friend here, well, he didn’t have a ring yet. It was sitting idle in a terminal somewhere in the greater Rochester area awaiting its final departure to the land of its newfound owner. In other words, FedEx hadn’t delivered it yet. This would be problematic, given that the shoot was scheduled for the next day at lunchtime. With it being scheduled to arrive, possibly before lunch, we were cutting it close. I was to have my camera gear ready regardless. 

That night I received a text message simply stating that the ring was delayed even further. This was now scheduled on a different day. This was fine for me, I’m not the one doing the proposing. All I knew was that I now had freed up my lunch hour to play euchre with colleagues. Hard to trump that.

I’ve learned a long time ago that you should bring your camera gear with you everywhere you go. This is primarily with landscape type photography since you never quite know when you’ll be inspired or see something worth capturing. I am extremely thankful for this lesson. 

It arrived.

The ring arrived that morning, the day everything was originally scheduled for. The day I was told we would not be doing the shoot. A day that I had absolutely zero reason to have my camera bag with me at work. This was happening, and it was happening today. Sorry euchre partner, maybe next time. I’m going undercover.

We arrived at the spot early to get set up. Unloading thousands of dollars of camera equipment in, what some would consider, a not-very-nice neighborhood caught some people's attention. Namely, one lady who was nursing a disguised beverage carefully encased in a brown paper bag. I’m not here to make assumptions. However, she did believe me to be a member of the paparazzi and that a celebrity was on the way. And she wanted to know who, like I would give the intel away for free...

The hour was drawing near, and I stood in full on landscape photography mode in the exact spot they would be proposing. Clever thinking, right? If I’m standing where he wants to propose then no one else can have that spot. And when was the last time you asked someone with a massive camera to move? This bad boy gets me wherever I want to go. Several people showed up just as the couple arrived. As fate would have it, they all migrated towards the far end of the overlook as if to suggest that I wreaked of body order. 

I was unrecognizable. She didn’t know me from Adam Sandler. In a timely way, I navigated away from the coveted spot and allowed the couple to stand in my stead. Backwards hat and sunglasses on, I likely looked way more suspicious than necessary. Subtle drinks of water (it was hot), fidgeting with my camera gear but not actually accomplishing anything, just another day for me. 

Naturally, as the moment drew near I became less and less subtle. She locked eyes on him and never looked away. I didn’t realized how loud my shutter was until I started spamming photos undercover. But I got the impression that an actual celebrity could have shown up and she would be none the wiser. 

I got it.

Six hundred photos later, I captured the entire moment and shot some posed portraits afterward for good luck. She immediately turns to me and says, “Is this the guy you hired to take photos?!” Hi. I’m the guy. Congrats. Now be cutesy and romantic again so I can do my job. Did she know I was taking pictures the whole time? Maybe, but I still nailed it.

This was quite an experience and I’m so glad I got to be a part of capturing it.