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 Dumetz, she starts to like Josh and they kiss and date at Spring Formal.