Jackson and Hailey met through their mutual friend, Braden Moore. They quickly became inseparable, and just a few months later began dating. Even before meeting her, Jackson had told Braden he knew he would marry Hailey.
In April of 2025, Jackson began planning the perfect proposal to Hailey. He arranged for their best friends, Wesley and Brynn, to “visit” for a July weekend. With the loving help of Brynn, Wesley, and his family, Jackson asked Hailey to marry him at the beautiful Newfields in Indianapolis.