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A Rainy Rooftop “Yes”: Sam & Maggie’s Charlestown Proposal

newly engaged couple in Charlestown

Sam and Maggie’s story has come full circle in the most beautiful way. These two Bowdoin graduates, now building a life together in Boston, marked a new chapter with a surprise proposal that was nothing short of magical.

On a rainy Friday night in May (wow, spring 2025 was a wet one!), Sam led Maggie up to their rooftop. There, surrounded by the quiet hum of the neighborhood, drizzling sky, and intimacy of the moment, he asked her to marry him. She said yes — and the celebration had only just begun.

Afterward, the newly engaged couple strolled through the peaceful, rain-kissed streets of Charlestown. The brick, quiet corners, and soft glow of the evening set the perfect scene for some dreamy portraits. Just when Maggie thought the night couldn’t get better, her family appeared with joyful hugs and happy tears down at the Navy Yard.

It was a night filled with meaning, love, and thoughtful surprises — a perfect beginning to their next chapter. Congratulations, Sam + Maggie!

Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
Boston rooftop proposal
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown

After photos at the Monument and Training Field, we wandered down to the Navy Yard where Maggie’s family was waiting to surprise her!

newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown
newly engaged couple in Charlestown

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