The 2 matched on the dating app, Hinge, in April of 2023. They continued to exchange messages on the dating app before moving to Snapchat. After continuing to converse for a while, they finally decided to meet up in person. They had their first date at Old Chicago in Liberty... and the rest is history.

If you ask Katelyn: Caleb was the farthest thing from the type Katelyn would normally go for, but she thought he seemed genuine so she swiped right to give him a chance. Caleb used the line, "All the good pickup lines are taken, but looks like you aren't." Katelyn decided to add him on Snapchat, mainly to see if he still was sporting the mullet that he so proudly presented in multiple pictures on his dating profile. She had decided that if he still had the mullet, it was going to be a no-go for her. He did not, so she agreed to meet up with him for a late lunch. Later that evening, Katelyn went out to Guitars and Cadillacs with her Aunt Lorie and had told her about him so that just shows that she thought their date went well.

If you ask Caleb: They met on Craigslist.... Not really. Caleb didn't think he was going to get a second date because they couldn't find anything to extend the first date, so he thought she just wasn't interested in him. Turns out there was a second date after all. She came over to his place in Louisburg and they both fell asleep on the couch watching Adam Sandler movies. Later on, Caleb and Katelyn made a stop at Cody's in Liberty while visiting with some of his friends (which Katelyn was meeting for the first time) and she had called him "babe" and that's when he knew he had been claimed.