Gretchen (2005)

Gretchen has bigger problems than abysmal fashion sense: She's 17, painfully awkward and stuck in the most unforgiving place on earth - high school. When her obsession with school bad boy Ricky gets out of hand, her mother sends her to an emotional treatment center to recover. She has to travel elsewhere, however, to truly begin to understand why she fixates on the wrong kind of guy.