Maddy moved to Nashville in 2020 and met Justin two months into living here. Maddy used to be a waitress at a Ruby Tuesday in Dickson where Justin lived. He was out with his family when they suggested they should go out to eat, and Ruby Tuesday happened to be the place where they ended up. Justin and his family ended up sitting in her section, however her coworker was their waitress not her. Justin caught Maddy's eye, but she was too shy to go up and say anything. It wasn't until they were getting ready to leave, and her coworker needed help with the card terminal. Maddy went over to assist with the payment, and the first thing out of Justin's dad's mouth was, "Are you single?". His dad was his wing man that night, and clearly it worked in his favor.