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Dylan Shoenfield is the pink princess of the upscale Woodlands Academy. She has the coolest boyfriend, the most popular friends, and a brand-new it bag that everyone covets, but when she accidentally tosses her Serge Sanchez bag into a fountain, this princess comes face-to-face with her own personal frog - self-professed film geek Josh Rosen. In return for rescuing Dylan's bag, Josh convinces Dylan to let him film her for his documentary on high school popularity. Reluctantly, Dylan lets F-list Josh into her A-list world, and is shocked to realize that sometimes nerds can be pretty cool. But when Dylan's so-called prince charming of a boyfriend dumps her flat, her life and her social status comes to a crashing halt. Can Dylan win the Woodlands Academy Spring Formal Blossom Queen crown? Can Josh win the Woodlands Academy 5th Annual Film Festival? Can Dylan, with Josh's help, pull the pieces together to create her own happily-ever-after?