I Photographed This Couple Mid-Proposal. Can You Help Me Find Them Using These Clues?

If there’s one thing a cold, gray, post-holiday January in New York City demands, it’s an escape to a warmer climate (should you be lucky enough to be able to afford it and make it work).

After close to 20 years in the city, I’d never been to Puerto Rico — even though it’s just a few hours away by plane — and neither had my boyfriend, Alex, so we decided on San Juan for our first vacation together.

On January 8, we took a walk along the Paseo del Morro. It’s a scenic and historic path along the walls of Old San Juan, offering incredible views of the seaside and encounters with the many cats that hide from the sun among the rocks along the water. The path eventually leads up to the Castillo San Felipe del Morro, a large fortress constructed between 1539 and 1790. Desperate to find some relief from the near 90-degree heat, we stopped at the top of a grassy hill overlooking the Atlantic Ocean to let the breeze cool us off. 

I’m a photographer by trade, and when I travel, I like to use film, so on this particular trip I had only brought my grandmother’s old Pentax K1000. Using film instead of digital is a way for me to slow down, pay attention to what I’m seeing and take the pressure off the need to shoot a high volume of images. 

I had just brought my camera up to my face to shoot a large ship that was passing by when Alex noticed two people standing at the end of the pier far below us.

“Are those people getting engaged? They’re getting engaged!” he said, pointing.

I snapped maybe six or eight images in a row as he recorded the moment on his phone. We looked around to see if anyone else was witnessing this serendipitous occasion, but we were the only ones.

We let the couple take their time, not wanting to impose on such an intimate moment. When the proposal appeared to be done, we made our way over to them, introduced ourselves, and I told them I had captured their engagement with my camera. They were delighted, so I asked for one of their emails and told them I would send the photos after they’d been developed. I wasn’t entirely sure if the images would even come out, as we had been a fair distance away and my light meter had stopped working, but I assured them if I had gotten anything good, I’d be in touch. We chatted a bit longer and then we congratulated the couple again and parted ways.

As Alex and I continued walking, we remarked how thrilling it was to have just witnessed this random couple’s proposal. It made me wonder exactly what it was about seeing two strangers get engaged that felt so exciting. We didn’t have any investment in their lives — knew hardly anything about them, and likely never would. Regardless, it was an incredibly significant moment for them, and to see something that rare and meaningful and unexpected happen right in front of us felt a bit like seeing a shooting star.

Extraordinary moments like these feel like a gift, especially in a world where so much is currently going wrong. Seeing two people making a commitment to each other — whatever that looks like for them and however they choose to honor it going forward — is a beautiful thing. It felt like I had been given a little reminder from the universe that despite how bad things can seem, love is real and we should do whatever we can to encourage and respect and celebrate it.

Alex and I returned back to New York City and last week, almost two months after our trip, I finally got my film back. Not only did the images of the engagement turn out, but I had one of every part of the proposal: getting down on one knee, their embrace after, all of it. Although the couple was far from where I was shooting, their beautiful experience was perfectly documented in my photos.

I couldn’t wait to share what I’d shot with the couple. I opened up my Notes app on my phone to retrieve the email they had given me but it wasn’t there. Somehow their contact info had gotten deleted. I was devastated.

“What do we do now?” I asked Alex.

We weren’t sure. How could we find two strangers with only a scant amount of information? We didn’t know, but we wanted to try.

So… this is us trying. Maybe someone reading this essay might know this couple and can help me get in touch with them so I can share my photos of their special day.

Here’s what we know:

The couple (we believe they were two women but we didn’t ask about their gender identities, so we can’t be sure) got engaged on the afternoon of January 8, 2024 at the Castillo San Felipe del Morro in Old San Juan, Puerto Rico. I think they were from Baltimore, or, if not, somewhere else in the Maryland or D.C. area. One of them was named Melissa. 

I feel lucky to have been in the right place at the right time to witness this couple’s proposal and I’m hoping a little more luck — and a bit of help from one of you — might finally get my photos to them. 

If you know these individuals (or you’re the couple featured in the photos), email [email protected] and we’ll get you in touch with Kathryn.

Kathryn Sheldon is a freelance still photographer and director of photography based in Brooklyn with a specialty in the culinary and hospitality realm. She previously worked at MTV and NBC Networks in New York. Follow her film photography on Instagram @sometimesitgrains.