Ashley and Jonathan swam for rival high schools, however since they swam in different practices they didn't ever officially get introduced to each other. In the summer of 2016 they both started working the same summer job and became friends. At the end of the following summer, after many shifts spent talking, he asked her out.

During the summer before their senior year, while at work one day, Jonathan asked Ashley if she would want to go see a movie with him on Friday night. Ashley was so excited that he had asked her out, she didn't realize she had a fundraiser for the swim team that night. Rather than reschedule, he volunteered to come pick up trash out of the football stadium with her after the movie.

After high school graduation, Ashley moved to Stillwater, Oklahoma to attend college at Oklahoma State University. This put over 300 miles and five hours of distance between her and Jonathan, who at the time was attending Amarillo College, and then later WTAMU. Despite taking on a full class load, and working full time, Jonathan made constant efforts to come visit Ashley at college multiple times a semester. The next four years were full of phone calls, Snapchats, and the occasional weekend round trip as they continued dating from different states.

Over the previous four years they had spent many dates walking around Medi Park. The first time they went there on a date, Jonathan pointed out the spot on the path where his dad had proposed to his mom. When the time came it was only natural that he would propose there as well. They climbed to the top of the rock wall, a few feet from where his parents spot was, to escape the angry geese at the bottom. Ashley stood looking over the edge of the wall and when she turned back around he was on one knee.