They met on Black Friday 2022 when the line of Under Armor crossed in front of the store Maddy was working in at the time. Tim saw this as an opportunity to go in and finally talk to her after seeing her from across the hallway for a while. After a few more visits to the store to talk to her, Tim finally got Maddy's number when she sent him the link to an online autism test. They texted back and forth for a while, and after a few shot-down attempts, Maddy finally agreed to dinner at Uncle Julio's in Columbia. On March 8th of 2023, Tim officially asked Maddy out by quoting one of her favorite Taylor Swift songs. Then, exactly one year later, he asked to make it a forever thing.