Dean and Caroline’s story began in Boston in 2021, when Dean was living there after college and Caroline had just arrived for her first travel nursing contract. What started as a match on Hinge quickly turned into something more when they met for lunch at Lolita’s in Fort Point, a “quick” first date that somehow stretched into four hours.

From the start, it was clear something clicked. They could talk endlessly, often about completely different things, and still be just as interested in listening as they were in sharing, even if they didn’t fully understand what the other was saying.

They spent the next few months exploring Boston together, walking through Boston Common, visiting the zoo, and finding any excuse to spend more time together. When Caroline’s contract came to an end, they made the bold decision to continue long distance while she traveled the country.

Long distance came with its own adventures — including one unforgettable trip when Dean flew out to Indianapolis to meet Caroline, and the two drove 17 hours back to Boston together. Along the way, they made stops at Cornhenge (yes, exactly what it sounds like) and the real prison where The Shawshank Redemption was filmed — a must-see for Caroline.

After two years, they finally closed the distance and reunited in Arlington, where Dean had taken a new job. Since then, they’ve built a home together along with their two mischievous cats, Mercury and Flavius, and settled into a life full of adventures, laughter, and just the right amount of chaos.

On their four-year anniversary, Dean proposed at Dumbarton Oaks, right near their home. It was as much of a surprise as possible and the perfect start to their next chapter together.