Maddison was a freshman in college when Ashton was a senior in high school. She began serving as the 6th grade girls' small group leader in their church when they first met. They never talked to one another until Ashton graduated from high school and began serving in the youth, as well. It all began with the annual D-Now registration night. They were manning the same table to help students sign in. His group of students were constantly circling the table trying to enter the main room. Maddison was getting frustrated with the consistent horseplay, so she said something to Ashton. This moment of nagging was all it took for the two of them to start talking to one another. They bonded over the struggles and successes of leading middle school students and that became the launching pad to their relationship. She thought he was caring and thoughtful. He thought she was compassionate and kind. He asked for her number, and they went on a few dates before he officially asked her to be his girlfriend on February 14, 2016.

Talk of getting engaged began around the summer of 2017. Ashton saved his money, he asked Maddison to send him some ring ideas, and together, they designed the perfect one. Maddison began getting anxious, constantly wondering when Ashton would get down on one knee and pop the question. It all came to a head on a Sunday in April. Ashton and Maddison had decided to go hiking after church, as it is one of their favorite things to do. She thought this would be the day he asked, but she became discouraged when Ashton revealed he had invited his sister and brother-in-law to go with them. Their original destination was closed due to flooding, so they tried somewhere new. They hiked up multiple trails, enjoying the overlook spots. Maddison may not have believed they were getting engaged that day, but she tried to enjoy every last bit of their time together. Since Spring was in full swing, they were determined to find bluebonnets. They were not having any luck until the very last trail they followed. Finally, there were fields of bluebonnets. It was picture perfect. Maddison was taking photos with her Polaroid camera when she turned around and found Ashton down on one knee in front of her. He didn't have a speech prepared but that did not matter to her. He asked, and she said yes. It was the happiest day of their lives.