It was September 2014. Kaysie decided to attend a friend's birthday at a local bar, Chasers, in Niles, right after her long shift at work. Clark happened to be in the same friend group and attended as well. The two caught each other's eye and exchanged numbers. Kaysie, being an extreme workaholic at the time, would barely answer any of Clark's texts. It wasn't until after an annual Wisconsin trip that Kaysie finally agreed on going on a date with Clark. Their first official date was at JoyYee's, which lead to many more foodie dates and adventures in the city. The rest became history.

In December 2019, Kaysie and Clark vacation to the Philippines for Kaysie's cousin's wedding. The day after the wedding, there was another celebration for the newlywed couple at Kaysie's grandma's house. It's not a true Filipino party unless there's some sort of Karaoke involved. Kaysie's cousin, Anjo, sang Ed Sheeren's "Perfect" while Kaysie watched and enjoyed the performance not knowing what was about to happen. After the song, Clark was up next to perform what Kaysie thought was another karaoke song, but Clark had another plan in mind. Clark proposed with Kaysie's family in on the secret! Clark popped the question and Kaysie undoubtedly said "yes!".