Despite attending the same school and growing up just a mile apart, Alyssa and Ben didn't cross paths until the summer of 2020 when they both found themselves back home, waiting out the uncertainty of the pandemic. One fateful night, they stumbled into the same bar, and from then on, Ben was determined. However, Ben was on his way to live in Chicago, while Alyssa was headed for Milwaukee. Despite the impending long distance, Ben was set on making it work. He officially asked Alyssa on a date, and from there, the rest is history. They bonded over their love of travel, spending weekends in both Chicago and Milwaukee. About a year later, Alyssa moved in with Ben in Chicago. Their adventures eventually took them to Portugal, where Ben proposed to Alyssa in a vineyard in the Douro Valley.