Mike & Madison | A Surprise Boston Proposal & Engagement Celebration
Some proposals are sweet. Some are thoughtful. And then there are the ones that are meticulously planned, family-filled, and wrapped in the most classic Boston backdrop—Mike & Madison’s was all of that and more.
Mike reached out to me ahead of time with a plan to surprise his girlfriend, Madison, while they had some family in the city visiting. Not only did he want their loved ones there to witness the moment, but he had also secretly planned a full engagement celebration afterward. From start to finish, this was one of those days that reminds me why I love being trusted with moments like these.
The Plan
The proposal took place on the Commonwealth Avenue Mall, right in front of the Alexander Hamilton statue. My role? Be in the exact right place at the right time—without raising any suspicion.
Enter my not-so-secret weapon: my 9-year-old son, who came along as my “reason” for being there. We casually hung out on the Mall while I snapped a few photos of my little assistant, waiting for Mike and Madison to walk up with their family.
The plan was simple and genius. The group would stop nearby and attempt to take a selfie together. I’d notice, offer to help, and take the photo on their phone. Once that happened, the family would step aside… and Mike would get down on one knee.
And that’s exactly how it unfolded.
As soon as the family moved away, Mike dropped to one knee and asked Madison to marry him. I immediately switched from “helpful passerby” to full-on photographer mode, capturing every second as Madison realized what was happening—her reaction, Mike’s nerves, and the family watching on with the biggest smiles.
After she said yes, even more family and friends popped out from where they had been hiding, surrounding the newly engaged couple. I was snapping away the entire time, which definitely earned me a few confused looks from Madison. At one point she clearly clocked me as that random woman still taking photos… until it finally clicked that Mike had hired me as part of the plan. Once she realized, we all had a big laugh—one of my favorite moments of the day.
Engagement Photos in the City
After the excitement settled, we walked across the street to the Boston Public Garden for a few engagement photos. It was chilly, with a light dusting of snow that made the city feel extra magical.
One of the highlights? Walking out onto the frozen duck ponds—something I’d never had the chance to do before. We wandered, chatted, and captured a handful of beautifully posed engagement photos that felt perfectly “them,” all while the city buzzed quietly around us.
From there, we made our way to the next surprise.
The Engagement Party
Mike had planned a full engagement party at Ruth’s Chris Steak House, located inside Old City Hall in Boston—an absolutely stunning spot for a celebration like this. Madison was completely surprised as they walked in to find a large group of family and friends waiting to celebrate them.
I captured the couple making the rounds, sharing hugs, laughing, and Madison proudly showing off her new bling. Mike’s sister went above and beyond with the sweetest details: a custom sign, matching napkins, and an adorable little cake to mark the occasion.
A Sweet Ending
Being part of such a thoughtfully planned day was an honor—and having my favorite little assistant by my side made it even more special. After everything wrapped up, I treated him to a mother-son dinner date as a thank-you, which he absolutely loved. We snapped a few of our own selfies along the way, soaking in the city together before heading home.
Mike & Madison, I’m wishing you all the best as you dive into wedding planning and begin this next chapter of your lives together. Thank you for letting me be part of such an unforgettable day.
