Annie battles the city mayor for the town's prestigious Oakie Award, when she refuses to remove the parking boot from the Mayor's SUV. The rest of the family grapples with the fallout from Annie's struggle, when the Mayor retaliates.
Duncan Harris is a spectacularly average 15-year-old boy, who is always one step away from making a bad decision. Along with Duncan lives his mom, a parking enforcement officer, who dreams of being a detective someday and always has to watch Duncan; his dad, who tries to be a better father figure to Duncan than his father was to him; his sister Kimberly, who is a normal teenager going through normal teen-phases; and his other adopted Asian sister Jing, who is an intelligent 5-year-old who is always giving Duncan advice. Mia is Duncan's on-and-off crush.