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Dylan Schoenfield is known as the "pink princess" at the posh Los Angeles Woodlands Academy. She has the coolest boyfriend, the most popular friends, and a brand-new bag that everyone wants. But when she accidentally throws her Serge Sanchez bag into a fountain, she meets her own personal frog, self-proclaimed film geek Josh Rosen. In exchange for saving Dylan's bag, Josh convinces Dylan to let him film her for his documentary on high school popularity. Dylan reluctantly lets F-list Josh into her A-list world, and she is shocked to learn that sometimes nerds are pretty cool. But when Dylan's so-called "prince charming" boyfriend dumps her, her life and social status come to a crashing halt. Can Dylan become the Woodlands Academy Fall Formal Blossom Queen? Can Josh win the Woodlands Academy's 10th Annual Film Festival? Can Dylan, with Josh's help, put all the pieces together to make her own happily-ever-after?