Brett and Ashley's first date was in Madison, AL in 2019. It started at Fulin's restaurant and ended with them grocery shopping at Publix. Ashley had driven down from Nashville to visit her family that Saturday evening and agreed to go to dinner with the guy she had been talking to on the phone for a few months prior. He lived in Alabama, she lived in Nashville. After dinner, Brett invited Ashley to go shopping for bananas with him at Publix. He wanted to spend more time together and wasn’t sure what else to do after dinner. She agreed, and they proceeded to walk around Publix talking as if they had been friends for years. After that night, they proceeded to plan the next few Saturday dates. Then, a few dates later, Brett and Ashley went to the Country Music Hall of Fame in Nashville where Brett asked her to be his girlfriend.