Ryan attended Southington High School in Southington, Connecticut. He started on the varsity squad his sophomore year and played a pivotal role on the offense as a receiver and running back. Catching passes from quarterback Dan Bruetsch, he became a dangerous offensive weapon and showed his potential. Glasper helped the Blue Knights win the CCC South crown. As a junior, he progressed to have a greater role in the offense, as he started at wide receiver, at running back, and on special teams. Glasper helped lead his team to another CCC South title. In the beginning of his senior campaign he was asked to play quarterback with the graduation of strong-armed quarterback Doug Fink (who was later drafted by the Boston Red Sox in the 29th round of the 2003 draft). Glasper eagerly took on the role and was progressing well until an ankle injury sidelined him. It was during this time that Glasper signed his letter of intent with Boston College to play safety on their defense. After signing his letter of intent, Glasper moved over to the defensive backfield full-time. While mentoring young sophomore quarterback Aaron Canterbury, Glasper helped lead the Blue Knights to a share of the CCC South title.