Loserville follows a dorky high school outcast named Chuck as he navigates the wild and confusing days of his senior year. Chuck must face the challenges that he and friends are growing apart; that his mother has decided to date a much younger man who just happens to be the school's gym teacher; and that his dream girl the brilliant, beautiful and popular Melissa Mercer barely acknowledges his existence. His plan to capture Melissa's heart once and for all by befriending her younger sister, Mary, is complicated by the fact that a viral video of Mary is the talk of the school. Featuring an ensemble of funny, flawed, and lovable characters who collide in a romantic, comic cocktail that turns every teen stereotype you think you know on its head.

An entitled young man with wanderlust must prove himself worthy of a new stipulation in his grandmother's will after her passing. The question before the law firm responsible for its execution is which will come first: the demise of the estate, or the realization of the heir that dealing with the past is the only path to true freedom?