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Chandler can't deal with the fact that Kathy simulates sex, half-naked, in a play, with a very handsome man. After Rachel is demoted to personal shopper, she is in a hard place after she discovers that she likes a customer. And Monica wants to play hostess again after telling Joey that since he now has the bigger apartment, he must constantly have company over.

Joey and Chandler guess all the items that Monica and Rachel had in a bag after coming home from the market. This starts a competition between the boys and the girls, a question-answer game created by Ross. The sex that knows the most about the other one wins. Meanwhile, Phoebe goes to the doctor to get the embryos implanted in her uterus. The game ends tied, so Ross prepares the "Lightning Round." Monica and Chandler raise the bet: if the girls win, the boys get rid of the chick and the duck, but if the boys win, they have to switch apartments. At the end, the boys win because the girls don't know Chandler's job. Just when the two couples are changing apartments, Phoebe surprises everyone announcing she is pregnant.

Phoebe considers her options when her brother visits with his new wife and asks her to carry their child. Joey works as a tour guide at Ross's museum and tries to tear down the walls between tour guides and scientists. And Chandler seeks advice from Monica and Rachel after he fears that he will not live up to Kathy's sexual expectations--especially since the last guy she slept with before him was Joey.

Ross must decide whether to continue dating a girl he must travel two-and-a-half hours to see. Chandler sets Rachel up with a coworker who misunderstands her intentions. Monica is being treated poorly by her new coworkers so she hires Joey just so she can fire him and show who's the boss. And Phoebe tries to write the perfect holiday song.

Chandler and Ross's college friend Gandalf is planning to come to town. Gandalf is "the party wizard." Ross and Chandler are very excited until Gandalf cancels. However, they decide to make their own party with Joey's help. Joanna squashes Rachel's chance at a promotion. And when Monica fills in for a friend as food critic for a small newspaper, she must decide between a steady job as head chef of a restaurant she panned or keeping her catering business with her friend Phoebe.

Chandler agrees to spend Thanksgiving in a shipping crate as penance for kissing Kathy. The gang decides to give each other Secret Santa gifts. After Monica gets ice in her eye, she ends up visiting Richard's son, who is as attracted to Monica as his father was.

Chandler must decide between the girl of his dreams and his best friend when he and Kathy share a passionate kiss. Needless to say, Joey is not happy to find out about Kathy and Chandler. And nobody wants to tell Ross how awful his keyboard playing is.

Ross's new girlfriend seems nearly perfect until he visits her house and discovers that her apartment is incredibly dirty. Chandler helps Joey pick out a thoughtful present for Kathy's birthday. Rachel attempts to finish a crossword puzzle by herself. And Phoebe helps Monica cater a funeral.

Chandler hits on a woman at Central Perk, not realizing she is Joey's new girlfriend. He soon realizes he is very attracted to, possibly in love, with her. Ross and Rachel play the jealousy game in their relationships. And Phoebe desperately tries to catch a cold after discovering that her voice is sexier and her singing better when she has phlegm in her throat.

Joey attempts ballroom dancing in order to help Monica and Rachel keep their illegal sublet. Phoebe is attracted to one of her massage clients. And Chandler has trouble attempting to quit a gym.