In August of 2023, Caroline and Gannett Loftus decided they wanted to set up Ashley and Will on a date. While Ashley was studying with them, they provided her a list of suitors, one of them being a homeschooled, BJU grad–although admittedly her selling point was that he was tall. On the other side of things, Gannett texted Will and told him “hey I’m gonna set you up on a double date-you in?” to which Will agreed. They played pickleball on the first date, with general “getting to know you” questions and Ashley embarrassing herself by not having a strong milk-shake order at CookOut, while Will came in strong saying that the name Ashley could work for a boy or a girl. Despite first date jitters, they decided a second date was on the cards. A week later, they went to Riverfront Park and walked the entire round trip just talking about everything. From then on, they became inseparable.