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Joss and Maguire have a deal that they sleep together when they want, but with no pressure, just sex. Later, he tells her that he is interested in someone else. Maguire and Sarah kiss outside the bar, but then she apologizes and tells him that she has a boyfriend in San Francisco. Maguire gets disappointed. Romy and J.B. try dating, realize they have little in common, but when they find out they're both lactose intolerant, they get together. Sarah gets a job as a decorator for one of Archer's rich friend, Mrs. Halloway, and is offered to live in their house. But she turns the job down, because she doesn't want anything handed to her as she had back in San Francisco. Sarah tells Bailey that she's decided to stay in New York.

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Sarah, Romy and Joss go on a quest to meet men in New York, and have a contest to see who can have the first meaningful dating experience. Romy meets a theater critic who turns out to be married. Joss dates a single father. Sarah goes out with a string of obsessive guys. Romy lands a national television commercial. Sarah takes a job as an au pair for Spencer's stepmother.

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