Kelsey and Regan’s story began as coworkers, but it didn’t take long for something deeper to take shape. From the very beginning, their connection felt effortless and simple. What started as conversations at work quickly became something they both looked forward to — realizing how many of the same interests they shared and how easy it was to just be around each other. Somewhere in those early days, there was a work bowling night — one of those small, ordinary moments that somehow became unforgettable. To this day, Regan is still convinced he won (in Kelsey’s memory, he didn’t). Around that same time, quick meetups for coffee started to become part of their routine. What began as occasional coffee dates slowly turned into something constant — an everyday habit, a reason to see each other, and a quiet foundation for everything that followed. In June of 2023, they took a trip to Martha’s Vineyard for Kelsey’s birthday — one that would come to mean more than they ever expected. During that first visit, they found themselves down at the wharf one evening, watching the Chappaquiddick Ferry go back and forth under the stars. It was one of those quiet, unplanned moments where everything felt still — and where they both, without needing to say a word, realized they had found something truly special in each other. From that trip on, the Vineyard became more than just a destination - it is now a place filled with so much love and memories.. and if you ever see Kelsey, there’s a good chance she’s wearing her Chappy crewneck or hat — a small, quiet reminder of that night and everything it came to mean. Through everyday routines, laughter over the smallest things, and life at home with their two cats, Xaco and Taco (named after their first date spot), they built something steady and real — a love rooted in comfort, trust, and choosing each other, every single day. (picture below of 2023 trip)
During a summer stay in Narragansett in August 2025, they spent the morning the way they often did — grabbing coffee at their favorite summer spot, Cool Beans Café, before heading down to Narragansett Towers to be by the water and admire the rock towers stacked carefully along the shoreline. Standing there, with the ocean beside them and the life they had built quietly behind them, Regan turned to Kelsey and asked her to marry him. And in a moment that felt so true to them — full of love, a little laughter, and a lot of heart — he was so overwhelmed with excitement that he had to ask twice, just to make sure he had actually said the words. Now, they’re so excited to begin this next chapter in a place that has meant so much to them from the very start — surrounded by the people they love most, exactly where their story always felt like it belonged.