Chloe is a New York party girl with the morals of a pirate. She causes trouble for her best friend James Van Der Beek and her naive small-town roommate June.

June moves to New York City to pursue her dream job at a mortgage company, which comes with its own apartment. However, the company is shut down on her first day and the apartment is taken away. June moves in with Chloe, a con-artist and all-round party girl. At first, they don't get along, but when Chloe's attempts to con June backfire, they end up becoming friends.