Kevin was a football star at St. Sebastian Prep. He was a popular student and tended to tease the less popular male students who applied themselves more than him, calling them "geeks" and "dorks". When Dorothy refused to pass Kevin due to neglecting his studies to party and have fun, his coach, Coach Odlivak (Frank Costanzo), who wanted him to be able to play in a big game that weekend, tried to bribe Dorothy by "offering" to take her out on a date; Needless to say, the proposition did not work, as Dorothy did not back down from her principles in refusing to pass Kevin, who looks at schoolwork and studies as something for "geeks". Dorothy's offer to compromise by giving him an "Incomplete" grade in English and to tutor him for a retest, so that he would be able to play in the big game does not sit well with Kevin or his coach. The Coach ultimately went over Dorothy's head and let Kevin play. When he gets injured in the game, Dorothy visits him at the hospital; He admits that people in his life had been trying to get him to apply himself for years, and finally agrees to allow Dorothy to tutor him on the weekends while he recovers from his injury. What becomes of Kevin afterwards is unknown.