Caroline and Jackson met on August 16th, 2018 at the annual Freshman Welcome BBQ at the University of Missouri. They quickly became drawn to one another and began officially dating on September 22, 2018. They both graduated from the Trulaske College of Business in 2022, and moved to Chicago to begin their post-grad life. On March 21st, 2025, Jackson surprised Caroline by getting down on one knee and asking for her hand in marriage.