A Boston engagement session offers the perfect mix of history, charm, and romance, making it an ideal backdrop for couples who want photos that truly reflect their story. For Brad and Rory, Boston is more than just a city—it’s where their love grew from a playful friendship into a lifelong commitment. Their engagement session in Beacon Hill, Charlestown, and the North End captured everything they love about the city and each other.
From College Friends to Soulmates
Brad and Rory first met during their freshman year of college. “There was always a playful flirtation between us, but we were friends first,” Rory shared. “We had mythology class together, and I later found out Brad would arrive early just to steal a few extra minutes with me before class started.”
Their bond grew over the years, and after college, fate stepped in again. Their best friends started dating, which brought Brad and Rory back into each other’s lives. What started as a close friendship blossomed into a deep and lasting love.
A Proposal with Meaning
Brad’s proposal couldn’t have been more thoughtful. On a warm May afternoon, he brought Rory to the town beach next to Rory’s family’s Cape Cod house—a place filled with childhood memories. With the ocean as their backdrop, Brad got down on one knee on the boardwalk and asked Rory to spend forever with him.
“It was just the two of us, sipping Coronas and soaking in the moment. Afterward, we ran into the ocean, celebrating our love in the most carefree and joyful way,” Rory said.
Choosing Boston for Their Engagement Session
Living in Charlestown, Brad and Rory have always loved exploring the city together. “We wanted our engagement session to feel true to us,” Rory explained. Beacon Hill’s historic charm, Charlestown’s cobblestone streets, and the North End’s romantic atmosphere made for the perfect combination of locations.
Each spot held special meaning for the couple, from favorite date-night restaurants to the streets they’ve walked countless times together. The resulting photos felt authentic, capturing the beauty of both Boston and their relationship.
A Glimpse at Their Wedding Day
Brad and Rory tied the knot in a dreamy waterfront wedding in Newport, Rhode Island. “Our wedding day was nothing short of magical—filled with sunshine, the love of family and friends, nonstop dancing, and the most incredible energy,” Rory shared. “It was truly a celebration of love, laughter, and unforgettable moments.”
Planning Your Own Boston Engagement Session
If you’re considering a Boston engagement session, choose locations that hold meaning for your relationship—whether that’s Beacon Hill’s picturesque streets, the waterfront, or your favorite neighborhood spots. These personal touches make photos feel more like you and less like a staged photoshoot.
Photography: Melissa Ortendahl Photography
Planning your own New England wedding or engagement session?
Check out more real love stories and inspiration in the latest issue of Evergreen Weddings Magazine, and follow us on Instagram @evergreenweddingsmag for even more ideas.
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