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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.

When Sarah is kicked out of her apartment by Romy, Archer offers her his place for the New Year's Eve. and Sarah finds out about Joss and Maguire's ""arrangement"". Maguire get robbed and Joss gets fired. J.B. backs out of his millennium dream date. Romy and Joss sit around eating candy and watching TV. Sarah almost ends up as a third wheel on Archer's millennium date, but instead gathers all of her new friends together to ring in the millennium with her on the street.