Caitlyn is an ambitious and confident 23-year old with a good job at a large head-hunting firm in Lower Manhattan. She’s determined out-perform her peers in the office, and snag a promotion when a major client presentation comes up for 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. Her worst fear is to become a stay-at-home-wife, like her mother and sister.
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 and Caitlyn finds herself intrigued by their uninhibited lifestyle.
She’s inspired by Michael’s casual sense of entitlement and indulgence. After having a threesome with the art school friends, she uses the cues from them 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.