Kevin and Anna met Spring Semester of their freshman year at Virginia Tech. At the time, Kevin was living in the cadet dorms with his roommate, Nathan, who happened to be close friends with one of Anna's best friends, Grace. Through those mutual friends, the two discovered that Kevin actually sat right behind Anna in one of their classes, Econ Food & Fibers Systems. After about a week of chatting with one another, Kevin and Anna had their first date: Breakfast at Joes Diner on March 2, 2019.

Kevin and Anna had been dating for almost 3 & 1/2 years before they got engaged. Over Labor Day weekend this past September, Anna flew out to Lawton, Oklahoma to visit Kevin while he finished his Army BOLC training at Fort Sill. On Friday, September 2nd, the day started as any normal day would, with Kevin and Anna running errands and doing other chores. She suspected nothing. Around noon, they headed to Mount Scout, with Kevin's friend, Josh, and his fiance Erin, to go sight-seeing before lunch. It was there, at the beautiful overlook with a bright blue lake beneath them, that Kevin got down on one knee and popped the big question.