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Having finally conquered the awkward, traumatic world of high school, Becky Freeley (Judy Greer) returns to her alma mater as a guidance counselor with her insecurities and orthodontia a distant memory. While Becky deftly navigates the uncertainties of troubled students and an often troubling faculty, she is certain of one thing - her desperate attraction to hot mechanic-turned-Spanish teacher Tim (Kristoffer Polaha). Now that it seems Becky might finally be getting the upper hand in life and love, she's shocked to discover that the newly hired English teacher is none other than her high school nemesis, Lisa Germain (Brooke Burns). Lisa is a smart, stunning beauty, and suddenly Becky is forced to relive her past and compete for Tim's affections.