Jackson and Roxane met at a brewery in Savannah. Roxane initially thought Jackson was too tall for her. Over IPAs and sours, they quickly found out they have many mutual interests: pop punk music, Ben Shapiro, and anime. A year into dating, in conversation, Roxane said "my three kids..." and Jackson said, "Wait I thought you only have two..."

Fast forward, they took a hiking trip to Asheville, NC. While admiring the beauty of the Biltmore's fully in bloom garden, Jackson, with his late grandmother's ring in tow, asked Roxane to be his forever.

Shortly after, the couple, alongside Roxane's three boys and Jackson's dog Fox, made the trek from the South to the Midwest, where they purchased Jackson's grandparents' farmhouse. They cherish the country life and look forward to making many more memories as the Whitcombs.