Keagan and Kailan met in early February 2020 at Keagan's going away party for his military deployment that year. For weeks leading up to their first meeting, Kailan was told on several occasions by Scott and Tina Kibler how she should meet their oldest son. Although at first Kailan wasn't interested in meeting someone new, she knew they were right when Keagan first walked into the bar that very day. Both were immediately smitten with each other and quickly bonded over several similar interests like their vinyl record collections, music, and their competitive nature over a game of darts. As Kailan's shift came to an end for the day the two made arrangements to see each other one more time before his deployment, but unfortunately plans had changed and the two promised each other a first date when Keagan returned from his deployment.

The two went their separate ways, but always found their way back to each other over the next several months maintaining their friendship and catching up when they could. Although it was very few and far between, both knew when the time came they were both ready to see where their friendship could go. A few short months before Keagan's deployment ended the two reconnected, but this time for good. As the two spent the next two months getting to know each other more and more, both immediately knew that they were talking to "the one".

Finally, on January 1st of 2021, Keagan returned home and the two have been inseparable since. The two finally got to have their first date after the excitement of Keagan's return calmed down. In true Kailan & Keagan fashion the pair spontaneously wound up in Chicago three hours away from home after the two decided it would be fun to enjoy the night there after a pitcher of margaritas and tacos at Ancho & Agave in Bloomington.

In October of 2023 Kailan and Keagan returned to Chicago once more, this time with bags packed and actual plans for their weekend. One of those plans included Keagan proposing on the Chicago River in a pink vintage boat, where the two promised forever to each other and the rest is history.