Though classmates in highschool, Casen and Kennedy met while he was the lifeguard at Kennedy's neighborhood pool. From then, the couple remained friends for over five years until deciding to finally date in 2018.

Casen took Kennedy, on what she thought a spontaneous trip to Austin, to go hiking at Mount Bonnell. The couple hiked up the mountain, had a picnic, and Casen popped the question all while Kennedy's favorite album (Golden Hour by Kacey Musgraves) was playing in the background.