Unfortunately for Joe, Kelley was splitting time between the US Virgin Islands and Boston at the time. As she traveled back and forth, the two kept in touch, meeting up here and there while Kelley was in town. It wasn't until April of 2021 that they went on their first "official" date at Beehive Restaurant in Boston. At a time when restaurants had a strict time limit enforcement in place, neither wanted the night to end.

From then on, Kelley decided to move back to Boston for good, and the two could finally begin what would turn out to be the best decision they would ever make - each other.

Soon after, Meghan, Mike, Kelley, and Joe, effectively orchestrated what was later referred to as "The Great Roommate Swap." Meghan moved in with Mike and Kelley subsequently moved into an apartment with Joe. As their relationship blossomed, they learned each other's idiosyncrasies and the overall nuances of living with a significant other. This further confirmed what both of them eventually came to realize - they wanted to take their relationship to the next level.

In July 2024, on the official day of their third anniversary, Kelley and Joe embarked on a private getaway to Kennebunkport, ME. After a sun kissed, beach filled day, the two had plans to visit Ocean Restaurant for dinner. However, Joe was being particularly pushy about arriving early and finding a place on the water to watch the sunset before their reservation. Kelley, finding this uncharacteristic of Joe, was a little perplexed by his newfound appreciation for punctuality.

At last, Kelley finished getting ready, and Joe drove them to a carefully researched spot on the rocks to watch the sun descend into the horizon. As the two spoke about how far their relationship had come, Joe knelt down on one knee and asked Kelley for her hand in marriage. Kelley responded with an emphatic, "yes!" and the rest is history...

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