After surviving the traumatic world of high school, Rebecca Freely (Judy Greer) returns to her alma mater as the school's newest guidance counselor. Now free of the insecurities of her teenage years, Rebecca immerses herself in the behavioral problems of the student body and lends support and guidance when needed. Rebecca must fend off the romantic advances of the persistent male nurse Gary (Jonathan Sadowski) as she lusts for the hot Spanish teacher, Tim (Kristoffer Polaha). However, in the ever-changing world of high school angst, Lisa (Brooke Burns), a former cheerleader and classmate of Rebecca's, also returns to the school as a new English teacher, forcing Rebecca to face her unpopular days of high school all while trying to win Tim's heart.