Conner and Kelsey met in the fall of 2016 and were close friends for nearly a year before going on their first date to the Ridgeland Dairy Queen. From that point, they started a nearly 6-and-a-half-year journey of being high school sweethearts. They were lucky enough to spend almost every weekend together as members of the Madison Central Speech and Debate team (serving as back-to-back Team Presidents). After finishing high school at Madison Central in 2019 and 2020, they moved to Oxford, Mississippi, where they attended Ole Miss. Conner received a Bachelor's in Secondary Social Studies Education, and Kelsey earned a Bachelor's of Accountancy and a Master's of Taxation and Data Analytics.

After nearly 7 years together, to celebrate Conner surviving his first year of teaching, and the recent end of Kelsey's accountancy internship in Nashville, they traveled together to New York City, where Conner finally proposed on a beautiful sunny day at the Bethesda Fountain in Central Park.