The first time Caleb and Amanda were in the same room was at a mutual friends apartment in college, however they did not physically meet until six months later. In May of 2019, Angel Lollar, who was Amanda's sorority little and also went to high school with Caleb, invited a group of friends to the local sports bar (Cool Beans) for a night of trivia. While playing trivia, Amanda got up to go to the bathroom and Caleb asked Angel how she knew Amanda because he thought she was pretty. Later that night, Caleb also went to the bathroom and then it was Amanda's turn to ask Angel who the new boy was because she thought he was cute. Angel knew this was her moment to shine and continued to set up group dates until Caleb and Amanda eventually realized they were perfect for each other. In October of 2019, Amanda invited Caleb to a date party for her sorority, then to her sorority formal in November, and they finally officially started dating in December of 2019.

Fast forward four years and Amanda and Caleb are hiking up lookout Mountain in Chattanooga, Tennessee to Sunset Rock. At the top of the mountain, Caleb asks a stranger to take a photo of them, and gets on one knee to ask Amanda to be his wife.