Caitlin and I met on Tinder and had our first date in August of 2018. We intended to just meet for a quick drink at The Distillery on Mount Hope because we both had to work early the next morning, but we ended up losing track of time and talking for over 6 hours until the bar closed and we got thrown out. We quickly began spending all of our free time together, with lots of hiking and adventures in the first few months. Our personalities meshed perfectly together from the very beginning, and our shared passion for the outdoors gave us plenty of things to do together. Caitlin quickly learned about my passion for photography, and soon found herself a frequent subject of my photos.
Just three months after we met, we took our first trip to Taughannock Falls together, and I decided to document the moment by capturing a photo of us in front of the falls. Of course, at that time I had no idea that we would return to the same waterfall 17 months later to get engaged!
The longer we dated, the more adventures we went on together and the further from home the adventures got. What initially started as day trips grew into weekend trips in the mountains and week long trips in other states.
We began hiking Adirondack High Peaks together and strategically working toward achieving our goal of climbing all 46. Our passion for the mountains grew stronger, and we started to overlook how much we had enjoyed our early day trips to the Finger Lakes.
Destin & Caitlin at Taughannock Falls, November 2018
Naturally, when I decided to propose to Caitlin, I began working out the requisite details to do so in the Adirondacks. We were planning a week long camping trip in Tupper Lake for July of 2020 with several friends, who I enlisted to help me pop the question. I wanted an easy mountain top with a great photo backdrop, so I began searching for the perfect location. On a previous winter high peak trip, I had climbed Baxter Mountain in Keene before driving home, and in doing so my friend Ryan captured the photo of me you see here.
I decided that this would make an excellent location to propose, and worked out all of the details. I booked an expensive hotel suite for that night and enlisted friends and roommates to sneak dress clothes out of Caitlin's apartment and into our hotel room. Ryan would join us on the hike to photograph the moment, and his Australian Shepard (@fen_the_aussie on IG) would hold a sign asking Caitlin to marry me. I had planned every. single. detail.
Destin on Baxter Mountain in the Adirondacks
They say that if you want to make God laugh, you should tell him your plans, and if that's true then my proposal plans sure gave him a good chuckle. For one thing, Caitlin had made it abundantly clear that she knew I wanted to propose in the Adirondacks and she thought that our upcoming camping trip would be the perfect opportunity. She also made it clear that she wanted to be surprised, which is difficult to do with a suspicious girlfriend and a plan that involves lots of people and moving parts. I was already beginning to second guess my plans when the world shut down due to a global pandemic. With both of us working in healthcare and the future suddenly seeming uncertain, I made the decision to speed things up and propose in the near future instead of waiting until summer. I still wanted an epic photo of the moment, so I began reaching out to photographers to see if anyone was willing to help me out, and I found that most were unwilling to work with clients because of Covid-19. Additionally, I knew that Caitlin really wanted it to be just the two of us with nobody else around, and I wasn't sure if a photographer violated that, but I decided I better not risk it.
When I realized that I would be photographing the proposal myself at the same time as I popped the question, I immediately began looking through my old photos for locations that I knew would work well for this purpose. I stumbled upon this shot that I took of my friend Ryan and his dog Fenway (the same ones who were going to photograph the ADK proposal and hold the sign, respectively) in April of 2017.
I knew that because it was the same time of year and the concrete retaining wall didn't move or change, the photo conditions would be predictable and easy to manage. I settled on this spot and invited Caitlin on an early morning photography adventure with me later in the week, which she was quite used to and I knew wouldn't arouse any suspicion.
I notified a few of her friends that plans had changed, obtained her parents blessing, and committed to ask the question that would forever improve my life.
On the evening of April 7, 2020 I informed Caitlin that we had to leave an hour earlier than originally planned due to "the sunrise conditions changing." This was a small white lie, as I had grown nervous that by 7am we wouldn't be able to have Taughannock Falls to ourselves. Caitlin was less than thrilled that we now had to set our alarms for 3:30am instead of 4:30am so I nervously told her that she could stay home if she wanted, praying that she wouldn't take me up on the offer to sleep in. I'm not sure if you know this, but it's kind of hard to propose to a woman who is asleep in bed 100 miles away. When the alarms went off the next morning I was already laying awake in bed because I had been too nervous to sleep. I woke Caitlin up, we gathered our things, and began the two hour drive. As I climbed into the truck, the ring box in my jacket pocket struck the door panel and made a loud clunk, which I was sure had given away my entire plan in an instant. Thankfully Caitlin slept for most of the trip, because I'm not sure that I could have kept a straight face to contain the surprise had she been awake. I've never been as excitedly nervous as I was during the final minutes of the drive or the short walk to the base of the waterfall, but somehow I managed to play it cool, at least according to Caitlin when I ask her about it today.
As we crossed the foot bridge and the waterfall came into sight, I noticed that the light and water conditions were absolutely perfect, and there wasn't another soul to be seen. Of course, I had to maintain the element of surprise, so I told Caitlin that the light needed for my planned landscape photos was still at least 30 minutes away and we had some time to kill. I suggested that we take some self portraits to pass the time, to which my still half asleep girlfriend complained that it was too cold and the waterfall mist would get her wet. Internally I was panicking, but I calmly assured her that the photos would be worth it and she hesitantly went along with my crazy idea. I set up my camera and tripod, composed the shot, and guided her into the perfect spot on top of the concrete retaining wall. I pre-focused on her and locked in my settings, and then in a last minute change of plans, I began recording a 4k video instead of taking photos with an interval timer. I figured I could use a screen grab from the video for my photo, and that having a video of the moment would be the proverbial icing on the cake. I tripled checked that the camera was recording, the focus was locked, and the exposure settings were correct, and then I jogged up and jumped onto the wall. I don't recommend last minute changes to technical details that could mess up your plans, but I broke my own rule on this occasion and it worked out quite well, thankfully.
Another thing I don't recommend is faking a proposal to a girl who really wants a ring on her finger, and I certainly advise against doing so repeatedly. Never one to heed solid advice, however, I had been doing "pump fake" proposals for a few months now. I figured it would help throw Caitlin off of my trail and provide for some good entertainment. Leading up to this, at least once on every hike or adventure I had gotten down on one knee in dramatic fashion and pretended to pull a ring out, only to tie my shoe or pick something up. Caitlin had been a good sport initially, but had become less amused with each passing "pump fake." When I hopped onto the wall to propose for real, I started by shooting her a sly grin and pretending to kneel down on one knee, which promptly got my hand slapped. She was cold, tired, and clearly didn't think it was funny anymore. Caitlin loudly exclaimed, "you're a jerk!" My reply to this was to kiss her, then pull out the ring box and say, "Oh, am I?" Then I lowered myself onto one knee, opened the box, told her that I loved her, and asked her to marry me. It took her a few seconds to gather her composure and even longer to get her left glove off, but she eventually said yes and allowed me to slide the ring onto her finger. Looking back, it's a good thing I didn't drop it into the rocks and water on the back side of the wall.
Not only is the photo you see below the resulting image, it's also my all time favorite photo. The day may come when I take a photo I'm more proud of than this, but I think it's pretty unlikely if I'm being honest. This image now hangs as a 20x30 metal print in our living room, and I smile like an idiot every time I walk by it. This photo is one of the inspirational building blocks that would eventually lead me to start Adventure Ahead Photography and begin specializing in adventurous wedding, elopement, and couples photography. Photographing my own proposal taught me just how meaningful a photo can be, especially when it combines the love you have for another person with the love for nature that you both share. I truly desire to help couples like us feel these same emotions when they look at their photos, so if this sounds like something you'd be interested in I would be absolutely thrilled to discuss the possibilities with you.
