A free-spirited 14-year-old (Hilary Duff) struggles to make the transition from life in the Big Apple to the rigors of a military academy after her mom marries a military career man. Gary Cole. Jennifer Stone: Christy Carlson Romano. Brad Rigby: Shawn Ashmore. Carla Hall: Andrea Lewis. Gloria Ramos: Aimee Garcia. Samantha: Linda Kash. Directed by Larry Shaw.