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Dylan Schoenfield starts off as a pink princess of the upscale Los Angeles Woodlands Academy who is snooty, wealthy, popular girl at school. A reformed dork, she now 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.
During the film-making, she is pretty rough on him, but soon they become super close. After being dumped by Asher, she starts to like Josh and they kiss and date at Spring Formal.