Maddie grew up in Alexandria, Virginia and attended the church where Sean's uncle, Gary, was the minister. Sean grew up 3 hours away in Williamsburg, Virginia. Maddie moved to the Charlottesville area for work, and made close friends with a couple that had a home on the top of Afton Mountain. Sean moved to his family's cabin on the top of that same mountain to work for the family business now based in Fishersville not long after. At a very fateful Halloween party at her friend's mountain house Maddie recognized Gary, and was so surprised to run into him so far from Alexandria so many years later that she decided to start going to church again. Maddie and her Dad, Ryan, became semi-regular attendees of the small church near Charlottesville where Gary had recently become the pastor. Gary often asked Sean to read things during the service to ensure his attendance, hoping that he could meet some friends in the area. Maddie and Sean couldn't help but notice each other in the small congregation of people mostly twice their age. One day, Maddie winked at Sean. Not long after Maddie came to church alone and Jennell, Sean's aunt and Gary's wife, suggested they sit together. Sean walked Maddie to her car that day and asked her out.