When spoiled Dylan Schoenfield (Sarah Hyland), Woodlands Academy’s most popular junior, accidentally drops her designer handbag into the mall fountain, the school’s film geek, Josh Rosen (Matt Prokop) jumps in to retrieve it. Although Dylan would not usually interact with Josh, to return the favor, she agrees to be the subject of his documentary for the school film contest – with the hope that the film will help her win the coveted Blossom Queen crown. While Josh sets out to make a hard-hitting film about Dylan and her social hierarchy, once the cameras start rolling he sees there’s more to her than meets the eye.