In 2017, Shain and Amy first met while playing on a trivia team together for the school Amy taught at, Smart Intermediate. The team was put together by Marguerite Dasso, a colleague and friend of Amy's and a long-time friend of Shain's. A week later, Amy and Shain connected again at a get-together at Marguerite and Drew's home in Rock Island. Amy learned of Shain's love of golf, while Shain learned of Amy's love for Mexican food and cool ranch doritos. After a couple weeks of exchanging texts, Shain convinced Amy to go on a date. Shain brought Amy to his favorite Mexican restaurant in Rock Island, El Patron. The rest is history :)