The day of the engagement, Jake and Kailey went to the Combat Air Museum in Topeka, Kansas. Like always, they held hands while on their way to and from the museum. Kailey caught him a few times looking at her hand, and eventually asked why he kept looking at her left hand. He played it off like she was crazy.

On their way back from the museum, their friend invited them to a bonfire in Cheney, Kansas. Jake told her it was an hour earlier than it really was to give himself time. While driving to Cheney, Jake used MacArthur Road for the route. He casually asked her if she would like to stop by Lake Afton at their spot for old time sake and she agreed.

Once they got to their spot, he kept the headlights on and turned on some music and grabbed her to two step. About half way through the song, Jake pulled out a ring and got down on a knee, and asked her to marry him. They got engaged on December 27, 2024 to Why Don't We Just Dance by Josh Turner.

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