Get ready for the best "how we met" story you'll ever hear! On May 16th, 2018, Kylie started working for the City of Cadillac Wastewater Treatment Plant as a seasonal worker doing lawn care and custodial tasks. Caleb had worked at the WWTP the year prior and was returning for a second year. He was nervous about "some girl" working with him at the WWTP. Terrified about her first job, Kylie may not have made the best impression on the first day, but over time it was clear that Caleb was smitten. After many laughs and sharing life stories in the work truck, a couple of after-work runs at Baker College and Kenwood Park, and an impromptu visit to Caleb's sister's graduation, Caleb and Kylie knew that they were meant to be. On June 14th, 2018, Caleb took Kylie out on his family's boat on Lake Missaukee and gifted her white roses, asking her to be his girlfriend.

In August of 2021, Caleb's family and Kylie took a trip to Italy to visit an exchange student the Mitchell's had a few years ago. They started the trip in Venice to stay with the exchange student and her family, though they traveled all over the country going to Cortina, Cinque Terre, Florence, Siena, and Rome. On their second full day in Venice, they toured St. Mark's Basilica and other areas of the city on foot. They had such a fun time seeing all of the boats and architecture, and eating amazing food! Towards the end of the afternoon, the exchange student and Caleb's parents were talking to every gondolier in sight trying to "find a good deal." (Kylie would later learn that they were trying to find a gondolier that would go underneath the Bridge of Sighs, where Caleb wanted to propose.) They finally found one and Kylie was so excited to be able to tour the city from the water! About five minutes into the ride, they were about to go under the Bridge of Sighs (Ponte dei Sospiri), and Caleb told Kylie about the bridge's legend: if you kiss beneath the bridge, you will have eternal love. He then told Kylie how much he loved her and the adventures that they get to take together, and he got on one knee and proposed beneath the bridge in the gondola! Of course Kylie said yes! She was so shocked and emotional! She literally cried the entire gondola ride. The whole trip felt like such a dream, and the engagement made it even more surreal!