On her first day at military school, she befriends Carla ( Andrea Lewis), a girl who has been there for a long time and shows her the ropes. Kelly has to enroll at the school, since it is the only school in the area, leaving behind her art school and her best friend Amanda ( Sarah Gadon).

When her new stepfather becomes the Commandant of a military school, George Washington Military Academy, Kelly and her mom move upstate. Kelly Collins ( Hilary Duff), is a free-spirited high school girl whose mother marries Brigadier General Joe 'Sir' Maxwell ( Gary Cole).