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In the premiere episode, June moves to Manhattan for a dream job and the perfect company apartment, only to have them disappear in a puff of reality, thanks to a CEO from the Bernie Madoff school of embezzlement. Deep in debt and out on the streets, June scrambles to land a job and a place to live. It seems that her luck has turned when she gets hired at a coffee shop and finds Chloe, a charming, vivacious roommate - but with the morals of a pirate. Chloe soon swindles June out of all her savings, but she and her snarky friend, James Van Der Beek (playing himself), come to learn that, just because June's naive, she isn't stupid. June ingeniously turns the tables on Chloe, who is so shocked about being scammed herself that she decides to pull June into her colorful band of friends. Sure, it's all dysfunctional, bizarre and overwhelming, but so is New York City. And with the help of Chloe and the other oddballs around her, June might just learn the survival secrets she needs to make it there.