Twenty-something Caitlyn Gregory is living some version of a dream in NYC, until she gets dumped by her college sweet heart, and fired from her dream job in a matter of days. Newly single and unemployed, Caitlyn takes counsel from her radical, art student neighbor, Paula, and is quickly beguiled by Paula’s friend Michael. His uninhibited lifestyle and casual sense of entitlement and indulgence inspire Caitlyn. As she battles the desperation of being jobless in New York City, Caitlyn detaches herself from her family, aggressively refusing their pleas to return home. She is determined to remain independent. Caitlyn figures something has to give, but she never expects it will be her.