Having recently moved back to Vermont, Kelsey was waiting in line at Ake's place—Burlington's premier watering hole—where Sam was somewhat of a regular. Kelsey noticed one of Sam's friends, Jared, wearing a Far Post jacket, which is coincidentally the club that her cousins grew up playing for and that Sam coached at. Conversation ensued, and when Kelsey asked how she could get involved, Jared offered to introduce Kelsey to "his boss". A number of drinks, laughs, and close dart encounters later, Sam turned out to be more interested in Kelsey than her coaching credentials.

No one will be surprised to hear that it was Kelsey who made the next move, asking Sam to go sledding at Burlington Country Club for their first date. Sam of course said yes before they realized one problem: neither of them had a sled. Kelsey's Aunt Meg & Uncle Keith came to the rescue with 2 snow tubes. The two had a great time, and to this day their love for snow remains an important part of their relationship.

Things were getting serious and as Sam and Kelsey both searched for new roommates, Kelsey decided to use the ace up her sleeve: her carport. Knowing Sam's admiration for the carport at her condo, Kelsey pitched the idea to Sam and sweetened the pot by saying, "you can have the carport". The deal was too good to pass up, although to this day Sam has yet to park in it.

When pressed on next steps, Sam would point to his "5 year plan". And to be fair, the plan was going well! S+K had grown immensely together, both graduating with master's degrees from UVM and starting new careers. They continued to coach soccer, adventure, ski, and bike. But time was running low on the 5 year plan. They started to dream about what was next and made a casual stop at Von Bargen's to browse at rings. As they walked out, the familiar sign of Ake's Place was right there in front of them. It felt like fate.

The wheels were now in motion. The casual trip to Von Bargen's turned out to not be that casual, and Sam moved quickly to make sure the 5 year plan stayed on track. Fast forward a few months and S+K were in Scituate for Christmas. Unbeknownst to Kelsey, the entire family (and even her boss) were conspiring to get her to Chatham so that Sam could finally bend the knee. But how? Kelsey's unsuspecting mother, Kathy, had a last-minute Christmas gift for a family friend that absolutely had to be hand delivered. The promise of a Corner Store burrito and fresh seafood to bring home to grill for dinner sealed the deal. Kelsey soon found out that it was all a ruse, as Sam popped the question while on a walk on Quitnesset beach. The perfect day was capped by dinner and a stay in Chatham—a tradition that the couple plans to continue each year on 12.22.