Woody and Bailey have known each other forever. Woody is good friends with Bailey's brother and five years older than Bailey. While growing up, Bailey had the biggest crush on Woody and would eagerly panic when he'd come over hoping he'd notice her... he didn't. In 2014, Bailey finished college and moved to Minneapolis. Bailey was home visiting for the holidays while Woody and Bailey's brother were living together, when sparks started to fly. They went on their first date winter 2014 snowboarding. Woody was an experienced snowboard instructor, and this was Bailey's first-time. Bailey hasn't been snowboarding since; but plans to! Bailey went back to Minneapolis. They continued to talk but due to the distance, nothing really developed. In September 2021, Bailey and Woody reconnected at her brother's wedding and they immediately began dating long distance. April 2022, Bailey moved in with Woody back in Wisconsin. December 2022, they bought a house! August 30th, 2023, Woody proposed to Bailey while on a late-night walk looking at the Super Blue Moon.