Billy & Maddy’s Surprise Seaport Proposal
I love a good secret—and this one was so good.
Billy first reached out to me after being recommended by one of my favorite couples, Bri & Max, whose wedding I was set to photograph. Little did Maddy know, as she and Billy danced the night away at their friends' wedding, a major surprise was already in motion. Billy had big plans to propose the following weekend… and only a few of us were in on the secret. I was photographing Bri & Max’s wedding with an extra little sparkle in my eye, knowing what was just around the corner for their sweet friends.
Billy & Maddy pictured here on the right, at their friends’ wedding the week before their proposal.
Fast forward one week later, and we’re in Boston’s Seaport. Maddy is enjoying a casual night out with her girlfriends—drinks, laughter, and a stroll through Fan Pier Park. The last thing she expects? To see her boyfriend Billy standing there waiting for her... especially since he told her he was tied up in an important work call back home.
Her friends, clearly in on the plan, subtly took her purse (a clutch move, quite literally!) and nudged her toward Billy. What followed was the most genuine reaction as Maddy spotted him—confused, surprised, and completely unaware of what was about to happen. Just like a lyric out of a Taylor Swift song, Billy dropped to one knee and asked her to marry him.
Maddy's face lit up with emotion and joy as she said, “Yes… of course, yes!” He placed the most stunning ring on her finger, and they shared a moment filled with tears, laughter, and pure love.
But wait—Billy wasn’t done.
From behind the bushes (yes, literally), friends and family who had flown in from all over popped out to surprise her again! Her reaction was everything—hands over her mouth, eyes wide, and so many happy tears. There were hugs, celebrations, and so much excitement as she proudly showed off her new ring to the people who love them most.
After all the happy chaos, I stole the newly engaged couple away for a few sweet engagement photos right there by the water. Maddy was still floating somewhere in the clouds—totally in shock in the best way. And, as if this proposal needed one more magical touch, a passerby happened to catch the entire thing on video, which later went viral on TikTok!
It was an absolute honor to capture this moment for Billy & Maddy. Being part of such a thoughtful, love-filled plan reminds me why I love what I do. Wishing these two a lifetime of laughter, surprises, and love!
