The Manhattan of 1995: a land without cell phones, but abundant in CD listening stations, bar smoke, and family dysfunction. Enter the Jacobs. Eldest daughter Dana's looming marriage to straight-laced Ben prompts a willful dive into her wild side, while her younger sister, Ali, is still in high school but leads a covert life of sex, drugs, and clubbing. After discovering love letters penned by their father, the sisters try to expose his apparent affair while keeping it from their all-too-composed mother.