During their early college years, Alyssa and Chris met thanks to an unlikely friendship between the VT Softball team and the Sinking Creek 4-Wheel Drive Association. After years of awkward silences and passing glances, in 2016, during their last year in school, Christopher got the nerves to ask Alyssa out and she said "yes". Following a first date at the River Brewing Company, there was no going back.

On a sunny afternoon in Hawai'i, Alyssa and Chris headed out to start off their birthday weekend with a beach day, nature walk and dinner plans to follow. Then the skies opened up and left them stranded in the pouring rain, in a town an hour away from home. With nothing to do for five hours until their dinner reservations, they made a change of plans. They headed home to bourbon, Primanti's sandwiches and birthday presents. Saving the best gift for last, after all their rained out plans and a perfect evening to follow, Chris proposed and Alyssa said "yes".