Alex e Greg Wheeler têm grandes expectativas para seu filho Jake, um brilhante e precoce filho de quatro anos que prefere Cinderela à GI Joe. Na véspera do ciclo de admissão para os jardins de infância de Nova York, ciente de que os pais de Jake não poderiam pagar a taxa de matrícula da escola privada, Judy, diretora da pré-escola do menino, encoraja-os a acentuar a expressão "variante de gênero" de Jake para que ele se destacasse e consiguisse uma bolsa de estudos.
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.