Strangers with Candy (1999)

Primetime comedy series that centers on Jerri Blank, a 46-year-old runaway, ex-con, former drug addict and alcoholic prostitute who returns to her parents' house and attends high school as a freshman. Faced with a new dilemma every week, Jerri brings each crisis to a tidy resolution by drawing all the wrong conclusions from high school's life lessons.