Jackson and Kaylee met the summer of 2017. Jackson was going into his junior year and Kaylee was going into her senior year. They hung out all of summer 2017, primarily at the Froehlich household. They had the best summer! Jackson finally asked Kaylee to be his girlfriend on August 13, 2017 after she bugged him for weeks about it. On August 22, 2025, Jackson finally got on one knee and asked Kaylee to marry him. This is the best days of their lives. As you can image, Kaylee also would not stop bugging Jackson about when he would ask her for her hand in marriage. August is such a special month for the two.