June is a Midwestern girl with big dreams when she moved to New York. She is hired at a coffee shop and things go slowly until she meets Chloe, who on the outside seems nice and inviting, but secretly is a swindler who takes June's savings and spends it. However, June is smarter than that and retaliates by selling all of Chloe's furniture. James Van Der Beek (playing himself) and Chloe soon learn that June may be naive, but she isn't dumb.
Chloe than fights back when June introduces Steven as her fiance by sleeping with him. June walks in on them "in the act" and breaks it off. June realizes that even Chloe didn't know it, she saved June from making a huge mistake. Chloe decides to invite June into her colorful band of friends and they go around and be friends.