In January of 2015, Caitlyn and Keaton met working for a minor league baseball team in Augusta, GA. Their relationship blossomed over their sarcastic personalities and love of sports, animals and crime dramas.

For weeks Keaton told Caitlyn for her birthday they were going to sit on the couch and watch Law and Order SVU. Little did she know that he planned to propose at a surprise birthday party with her friends and family. With Kooper in tow, they drove to Tuffys in downtown Sanford for a "wine festival", or at least that is what he told her. An hour and a half into the party, Keaton outfitted Kooper in a bow-tie and handed Caitlyn a scrapbook of memories with an important question at the end.