Dylan's earliest memory of Kayla actually dates back to Middle School. They were on the same bus route half of the week (when Kayla was going to her Mom's house) and though they never talked, Dylan remembers Kayla because the bus was always significantly quieter when she was on the other bus route to her Dad's house. They didn't actually interact until senior year of high school, though they shared classes since the seventh grade. Senior year, Kayla and Dylan were in both AP Physics and Italian together and would frequently ask each other for help. Their friendship slowly grew into more when Dylan asked Kayla to the senior prom on St. Patrick's Day, 2015. At the time, they were genuinely just friends but they both were secretly hoping it would turn out to be more. A few weeks later, Kayla invited herself on their first date - asking Dylan to take her for a hike since she had never been. They hiked Breakneck Mountain on April 12 - a mountain overlooking the Hudson River. They are so excited to get married overlooking the same river.

Dylan left for basic training at USAF Academy in Colorado on June 24, 2015 - just two days before his and Kayla's high school graduation. Nobody was sure whether or not their new relationship would last, especially with Dylan being in basic and having no access to phone for the entire summer. Kayla sent letters to Dylan nearly every day and he responded as often as possible. They exchanged their first "I Love You" through letters. Kayla left for the University of Florida at the end of that summer, right around the time Dylan finished basic training. She visited Colorado Springs for the first time that September - this is when they both say they knew they would stay together. For four years, they made trips to see each other in their respective cities (and time zones!) and spent many hours on FaceTime. Spring of 2019 concluded their long distance when they each graduated and moved to Enid, OK for Dylan's first assignment at Vance AFB.

Though Oklahoma has no mountains that can compare to Breakneck Mountain where they had their first date, Dylan and Kayla got engaged atop a beautiful Oklahoma plateau called Gloss Mountain. They drove out on a Friday evening and arrived around sunset. They hiked to the top and though Dylan planned to walk around for a bit before actually proposing, he quickly dropped to his knee and asked Kayla to marry him. Dylan was thrilled and Kayla cried tears of joy. They took some quick pictures before calling all of their parents who were waiting excitedly by their phones. It was such a special night and the love that was shared between both Dylan and Kayla and their families is something they will cherish forever!