Will and Sassy first crossed paths at Oceana Middle School when Will moved to Wyoming County. Sassy quickly became close friends with his sister, Chloe, while Will was the typical annoying younger brother who always tagged along. Over the years, Will not so secretly developed a crush on Sassy, though he was a little younger. Eventually, they both found themselves in college, where their paths crossed again. For a few months, they enjoyed a friendly connection, with a bit of harmless flirting on the side. Then, on Christmas 2021, Sassy playfully asked Will to be her "holidate" (yes, like the movie). From that moment on, they’ve been inseparable.