A wide-eyed Midwestern girl moves to New York City to pursue her dream job only to find herself living with an outlandish girl with the morals of a pirate. June's (Dreama Walker) well-planned well-organized life takes a drastic turn when she arrives in New York to find that the corporate finance job she moved there for no longer exists. As she tries to navigate her newly single life in the big city, her Midwestern scruples are constantly put to the test by her wild and sophisticated party-girl roommate Chloe (Krysten Ritter) and Chloe's best friend, the actor James Van Der Beek (James Van Der Beek). The two girls form an unlikely friendship that leads them both to unexpected places and often-illegal experiences.