In the fall of 2011, ambitious and confident Caitlyn is a 23-year old Junior Placement Specialist at a large head-hunting and recruitment firm in Lower Manhattan. Determined to succeed and out-perform her peers, Caitlyn is dead-set on snagging a promotion when a major client presentation comes up from grabs. Her long-distance boyfriend, David, wants more security in their relationship. But Caitlyn has zero interest in marriage and even less desire to move back to Boston and work for her father, or worse yet become a stay-at-home-wife like her sister and mother.

She’s fired the day after David breaks up with her. Newly single and unemployed she takes counsel from her radical neighbor, an art student named Paula. Paula introduces Caitlyn to Michael, the charming but slightly disturbed creative entrepreneur. Caitlyn finds herself intrigued by their uninhibited lifestyle. She’s inspired by Michael’s casual sense of entitlement and indulgence, and uses the cues from her two new acquaintances to battle the desperation of being jobless in New York City.

Something has to give, Caitlyn decides. She doesn’t expect it will be her.