All Hands on Deck: A Moody Boston Sailboat Proposal with Mara & Meghan

My job is more than just to take good photos. I want to be a provider of a good day: your day-of wingman who helps with the little things, keeps the secrets, and does whatever it takes to make the experience a good one. Mara and Meghan’s proposal was a pretty perfect example.

Mara reached out to me with plans to propose to her girlfriend, Meghan. The plan was a romantic sailboat, dirty martinis, and a sunset over Boston Harbor.

Very much up my alley.

There was just one logistical challenge: Mara and Meghan would be together all day, so we needed to figure out how to get everything onto the boat without Meghan noticing. I do photography because I love photos, but also because I love stories, and I always want to do whatever I can to make yours the best it can be. For Mara, that meant picking up a nice bottle of champagne, a few glasses, and a bouquet of flowers before heading to the Seaport.

I met the captain, got everything onto the boat, and prepared for my role as a deck hand, which is very much not up my alley. After retrieving Mara and Meghan, who got a little lost on the way, we unmoored and headed out onto the harbor.

The weather was a little touch and go. It was cloudier than expected, with a small chance of rain toward the end. Instead of the warm, golden summer sunset we’d imagined, the evening became something moodier and more cinematic. A little nautical, a little Little Women. Honestly, it suited the evening perfectly.

The proposal was intimate and beautiful. Afterwards, we broke out the pre-bottled dirty martinis and let things loosen up. We sailed around the harbor, laughed, popped the champagne, and eventually embraced the rain when it finally came.

As a Boston proposal photographer and LGBTQ+ photographer, I’m lucky to get to witness days like this, but what stayed with me afterward wasn’t just the proposal itself. It was all the little things that happened around it: sneaking champagne onto a sailboat, pretending to be a deck hand, the clouds rolling in, the martinis afterward, and three people laughing as the rain came down.

The day reminded me that my job isn’t just to take good photos. It’s to provide a good day. To help with the plan, take care of the little things, and make sure that when you look back, you remember not just how everything looked, but how it felt.

With good people like Mara and Meghan, that job isn’t so hard.