Stephen has been best friends with Sarah's cousins Jason and Dane Cooper since they were in high school. Growing up, he (and the Martin family) spent many nights and holidays at Grandma and Grandpa Capone's home in Athens, GA. He became the adopted 18th grandchild.

During Jason's wedding weekend in October 2012, Sarah's dad Ken bought one of Stephen's Jaguar cars, and they stayed in touch through the years.

In September 2015, the Capone family had a party up north. Stephen was in NYC for work. Ken gave Sarah Stephen's number. They spent the weekend together, and then decided to get to know each other more.

They kept the first few months of their relationship private to determine how serious they were with each other. When Sarah told her grandmother they were dating, Grandma Capone said "You better treat him right, don't you go breaking his heart," a testament to how much Stephen meant to her and Grandpa.