Stephen was inducted into the Chester County High School Beta club his freshman year. By the time he graduated, he had served as President, Historian, and Campaign Manager for Rebecca Haithcoat, the Tennessee State Beta Vice President. Some of Stephen's most memorable times from high school consisted of trips to Nashville for the annual Beta Convention. His senior year, and final trip to the convention, Stephen delivered the state-wide devotion before his lifelong friend, Rebecca Haithcoat gave the night's address.
Although the campaign to run Rebecca as the national Beta Vice-President was unsuccessful, the trip the Opryland Hotel will not be soon forgotten. While his friends and yearly convention roommates, Phillip Robison, Ronnie Geary, and Payton Reddin, were off chasing girls, Stephen and his friends Rebecca Haithcoat and Misty McPeake were having, perhaps, the best time that Stephen remembers from high school. "I can't tell you exactly what were doing. But, when you're with Rebecca and Misty, you know that you're going to laugh your butt off," Stephen said. Later on that night, the trio took a picture which currently hangs in Stephen's living room. Stephen said, "We all look so happy. That's so hard to capture on film." Sadly, Misty McPeake passed away in 1999 due to cancer.