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Ruby is a down-on-her-luck woman who can't seem to keep a boyfriend, a job, or get out of her parents house. But after she encounters a quirky woman in Central Park, she's handed the keys to a store in the Hamptons to manage. Determined to be the boss-babe that can make it our East, she makes connections with a variety of locals with entangling stories that make up the spirit of her new life.