Annie + Matt | Engagement at Boston

Boston has a way of wrapping you in its charm, especially in the South End. On June 18, 2025, I had the joy of photographing Annie and Matt’s engagement at Boston, MA, right in the heart of their neighborhood at Annie’s home on 577 Tremont Street. Their engagement wasn’t just a celebration of what’s ahead, it was a reflection of who they are— honest, grounded, and full of intention.

From the very beginning, I knew this wasn’t going to be a traditional engagement shoot. It was personal from the beginning. They welcomed me into the space where we walked up and down their street, pausing only for laughter, a dip on the cobblestones, and a few quiet in-between moments. Every frame felt like a glimpse into their everyday life: comfortable, joyful, grounded.

From Church Friends to “Let Me See the Ring!”

Annie and Matt first met at Grace City Church, just blocks away from Annie’s apartment. She had been attending since fall of 2021. Matt joined a bit later, in January 2023. While both of them were secretly eyeing the other from across the sanctuary, it all began with friendship and a few group hikes around the city. Annie started to flirt, and Matt caught on. A few shared laughs later, they were on their first date at Sulmona in Cambridge.

They ordered two pasta dishes and shared everything, though Annie admits that was more her idea than Matt’s. After dinner, they walked to the Longfellow Bridge for one of the best views of the Boston skyline, ending the night with ice cream at Toscanini’s.That simple, thoughtful night became a starting point for something so much deeper.

A Boston Proposal with Layers of Surprise

Fast forward to October 19, 2024. Matt planned an elaborate proposal with a guest list of surprise visitors including Annie’s parents and best friends from North Carolina, and his family from Philadelphia. The day began with brunch reservations at Buttermilk & Bourbon at 11am. But food was the last thing on either of their minds. Nerves and excitement made even the fluffiest biscuits feel heavy.

After their “meal,” they took a walk toward the Boston Public Garden. Matt had been up since 5am, already scouting the perfect tree branch to propose under. When they arrived, Annie spotted the photographer (a friend from church) in position. That’s when it all clicked.

Before Matt could even finish his proposal speech, Annie was bouncing on her toes and said, “Let me see the ring!!” It was the most “them” moment ever—full of energy, personality, and spontaneity.

After a quick photo session, they stopped by the Boston Public Library for a celebratory drink. What Annie thought was the end of a sweet proposal day turned out to be just the beginning.

The next stop: a “surprise” visit to Matt’s parents’ house. But when they arrived, both families and Annie’s best friends were there waiting. Backyard tacos, homemade ice cream cake (Annie’s favorite dessert), and plenty of hugs filled the afternoon. The evening wrapped up back at Matt’s place, where even more friends from Grace City Church were gathered to throw Party number two; complete with cake, champagne, and lots of cheering.

Annie had an idea the proposal might happen that weekend, but not like this. It was layered with love, intention, and just enough mystery to keep her guessing.

A Walk Through Their Neighborhood

Annie and Matt’s engagement session in Boston felt like a relaxed afternoon stroll through a neighborhood they know by heart. We started right outside Annie’s home on Tremont Street, where cobblestone paths, brick facades, and leafy greens framed each image with classic South End charm.

They wore light, neutral tones. Annie in crisp white and Matt in sage green and beige that blended effortlessly with the soft summer tones of the city. Whether they were walking arm in arm, laughing mid-step, or sharing a quiet moment, there was an ease between them that didn’t need direction.

One of my favorite moments was when Matt leaned Annie back in a playful dip in front of the brownstone steps. Her laughter was instant, his smile even bigger. It wasn’t staged—it was just them. Natural, connected, and totally present.

Quiet Moments and Honest Connection

For the second part of their session, Annie and Matt changed into something slightly more formal. Annie wore a flowing peach and yellow floral dress, and Matt stepped into navy pants and a crisp white shirt. As the golden light began to soften, we met outside the Boston Public Library.

Set against towering iron gates and limestone pillars, this part of the session brought a quiet stillness. Annie and Matt swayed together on the front steps, exchanged glances with knowing smiles, and paused in between to laugh and reset. I didn’t need to over-direct them. They simply settled into the space.

The inscription over the door read “Free to All,” a fitting message for a couple who deeply values honesty, faith, and shared connection. The best images came in the pauses: Annie nestled against Matt’s shoulder, their hands gently intertwined. There was a sense of calm here, even in the heart of the city.

Rooftop Views and a Boston Sunset

As the sun began to dip behind the skyline, we climbed to the rooftop of Annie’s building for the final chapter of the session. The city behind them was glowing, glass towers reflecting peach and violet skies, streetlights blinking on below, and string lights curling along the railing.

Annie tied her hair back, a small change that added a relaxed elegance to her already glowing presence. Matt wrapped an arm around her waist, and they quietly swayed to music only they could hear. They twirled, laughed, leaned in close, and paused in silence with the city wrapped around them.

It felt like their own little corner of Boston, a space where the chaos faded and all that was left was the two of them, dreaming forward.

Life Right Now: Pasta, Hikes, and Wedding Plans

Currently, Annie and Matt are in full wedding planning mode but they’re doing it their way. Most of their big decisions are behind them, and they’re finally getting to focus on the details that truly matter. They care most about the details that reflect who they are, intentional moments, time with family, and a celebration grounded in their faith.

When they’re not planning the big day, you’ll likely find them hiking in New Hampshire, experimenting with new recipes, or browsing local markets for fresh pasta. And of course, dessert is never far behind. Ice cream runs are a staple in their relationship, simple moments that continue to bring joy.

Their Advice for Couples Planning a Wedding

Annie’s advice is honest and refreshing: step away from social media.

“Once the big decisions are made, don’t get caught up in what everyone else is doing,” she says. “The more I scroll through wedding content online, the less joy the process holds. When I focus on who I’m marrying and why, it puts everything in perspective.”

It’s a reminder that planning a wedding isn’t about competing or comparing— it’s about staying grounded in your purpose.

A Wedding Vision Centered on Faith and Family

At the heart of it all is their faith. Annie and Matt are building their relationship on the Gospel and want their wedding to be a reflection of that. They’ve intentionally chosen a venue where their families and closest friends can stay for the weekend. They’ve made space for kids to run around and play. For Annie, the slow, quiet moments, getting ready with her mom, mother-in-law, and bridesmaids, matter more than any timeline.

They know that many guests will be traveling long distances, so they’re also planning one heck of a celebration; complete with a band and to share why they love New Hampshire so much. They want it to feel like a gathering, not a performance. A weekend where everyone feels at home

A Glimpse Into What’s Next

Photographing Annie and Matt’s engagement at Boston, MA was a reminder of how beautiful it is when a couple stays true to themselves. It wasn’t about a perfectly styled backdrop or the latest trend. It was about real connection. Their session captured more than a milestone—it captured a rhythm, a place, and a season of life that they’ll always remember.

To Annie and Matt,

Thank you for inviting me into your home, your city, and this chapter of your story. I’m honored to be a small part of it and letting me tell this part of your story. I can’t wait to see what’s next.

Here’s to what’s ahead, and all the beauty in just being where you are.