Monica is offered a great job in New York City and Chandler, unable to get out of moving to Tulsa, is forced to commute back and forth between the two cities. Phoebe and Joey set each other up on blind dates. Joey finds a complete stranger named Mike (Paul Rudd) for Phoebe's date. Rachel's pediatrician, Dr. Weiner, drops her due to her obsessive phone calls. She then takes Emma to Dr. Gettleman, Ross and Monica's pediatrician as children, but learns that Ross is still his patient.

Ross and Rachel hire Sandy (Freddie Prinze Jr.), a male nanny. Even though Sandy says he is straight, Ross finds him a bit feminine and does not like the influence he has on, not only Rachel, but Joey as well. After finding out that Sandy plays the recorder, can bake and does puppet shows, Ross fires him. Sandy does not take it badly, and instead comforts Ross about his childhood which involved bad memories of his father Jack.

Chandler, while in Tulsa, freaks out when Monica tells him that a man in her restaurant called Jeffrey is the funniest man she has ever met. Shocked, he returns to Manhattan and desperately tries to make Monica laugh but to no avail. After confiding in Joey about this, Chandler did not expect that Joey would go and tell Monica and Ross. The three try to make him feel better and Monica even lies by saying that Jeffrey made a really sexist joke when, in fact, Jeffrey made everybody laugh really hard.

Meanwhile, Phoebe and Mike exchange keys, advancing their relationship further. Phoebe's ex-boyfriend David (Hank Azaria) returns to New York for a meeting and comes to her house. A talk between the two of them enters into a romantic area when Phoebe hesitates to say that she is currently in a relationship. Then, after a talk with Monica, Phoebe admits to David that she is dating Mike and he agrees not to restart their relationship, but they end up kissing before Mike enters her house. Shocked at first, Mike forgives Phoebe once she tells him the entire story and David leaves.

Note: This is the longest episode of Friends (apart from the two-part ones), running 31:56. This is also the 200th episode.

Rachel is jealous that Ross can make Emma laugh by singing "Baby Got Back". Phoebe meets Mike's affluent parents and tries impressing them with a snobbish accent. Chandler and Joey find a videotape in Richard's apartment with Monica's name on it.

Rachel's sister Amy (Christina Applegate) unexpectedly shows up at Thanksgiving, so Rachel invites her to join the gang for dinner. Meeting Emma prompts Amy to bizarrely raise the question of Emma's custody if, hypothetically, Rachel and Ross were both to die. Rachel and Ross's answer upsets both Amy and Chandler. Meanwhile, Monica is acutely anxious about their expensive china plates they are using for the first time, and Phoebe tries to coach Joey how to lie convincingly, after Joey forgets to go to the Thanksgiving parade for Days of Our Lives.

On a girls' night out with Phoebe, Rachel gives a guy her phone number, but instantly regrets it after realizing she would need to move on from Ross. Joey thinks Monica is having an affair when Chandler claims he needs to work, as he does not want to lie to Joey about wanting to spend time with Monica rather than going to a game with him. While Phoebe and Rachel are out, Ross invites Mike to hang out, but they struggle to find something to talk about.

Chandler, stuck in Tulsa on Christmas Eve, notices the low morale in the meeting he is in and sends all his colleagues back to their homes. However, a female co-worker Wendy (Selma Blair) stays back with him after angering the insurance workers. While talking to Monica, he notices that she is becoming paranoid of Wendy and thinks that he is cheating on her. After convincing her that there is nothing going on between him and Wendy, Chandler ends the call, only for Wendy to make a pass at him. Having had enough, he quits his job and makes it home to Monica and his friends in time for Christmas. [This story serves as a framing device for the fifth of Friends' six clip shows.]

Rachel returns from maternity leave early when she fears the temp Ralph Lauren hired as her replacement might be given her job permanently. Meanwhile, Joey helps Phoebe out by convincing the Days of Our Lives director to hire her as an extra on the show, but it ends up being a disaster.

Phoebe adopts an orphaned rat family. Ross and Rachel hire a new nanny – Molly (Melissa George), but Ross becomes concerned when Joey starts hitting on her. He is relieved to discover Molly is a lesbian, but Joey is more encouraged. Rachel continues quarreling with Gavin, but when he arrives with a gift for her at her birthday party, they kiss on Monica and Chandler's balcony; unbeknownst to her, Ross, caring for Emma, sees them.

Phoebe urges Monica to sing at Mike's piano bar. The audience loves her but this may be because the spotlight reveals she is not wearing a bra under her see-through blouse. Meanwhile, an angry Ross is thinking Rachel is moving on without telling him, so her tries to find a date, eventually taking home a woman who just broke up with her boyfriend. Rachel arrives, wanting to talk with Ross, and after a big argument, she takes Emma and moves back in with Joey.

Special Guest: Paul Rudd as Mike & Dermot Mulroney as Gavin

To get Ross and Rachel to realize they are perfect for each other, Phoebe and Joey set them up on bad blind dates: Phoebe sets Rachel up with a unpaid shirt-maker who criticises himself and tries to make others feel pity for him while Joey, accidentally finding Ross "his perfect woman", tells the date that it is off, making Ross think that the date stood him up. At the end of the episode, Ross and Rachel come to the conclusion that Phoebe and Joey intentionally set them up on bad blind dates and the episode ends with Ross and Rachel chasing Joey and Phoebe out of Central Perk. Meanwhile, Monica and Chandler babysit Emma, but when Monica realises she miscounted the dates she is ovulating, the couple hurriedly run off to the next room to have sex, oblivious to baby Emma. Joey hears them having sex and, shocked, takes Emma out of the apartment.

Phoebe and Ross get mugged by one of Phoebe's old friends from the street (Kyle Gass), but when her friend recognises her, he lets them go. Ross then finds out that Phoebe was the person who mugged him when he was a teenager and stole his original comic book "Science Boy". Meanwhile, Chandler lands an unpaid advertising internship, but feels out of place due to his age after seeing that the other interns are teenagers. Joey auditions for a Broadway play starring Leonard Hayes (Jeff Goldblum), but must go to painful extremes (including holding his pee inside for hours at a stretch) to get the part after Hayes says that he is not acting urgently.

Chandler and Monica separately ask Joey for a loan. When Chandler discovers Monica asked Joey for money, saying Bings never ask for money, Joey claims Monica needed the cash for a boob job. Rachel tries to baby-proof the apartment by herself but realizes she cannot, so she hires a handyman. This results in Joey desperately trying to open the refrigerator and, once he does, taking all the food out so that he does not have to try and open it again. Mike tells Phoebe that he never wants to marry again, which leads Phoebe to question if they should live together. After a heartbreaking decision, Phoebe ends things with Mike after realizing that she does want to get married.

The gang buys lottery tickets and fight over how to divide them up. Chandler waits for a job offer at the advertising agency, while Rachel and Ross anticipate Emma's first word, which ends up being "Gleba".

Rachel struggles with her feelings for an oblivious Joey, who holds a Days of Our Lives cast party, but does not want any of his friends to attend. Ross develops a crush on another professor, Charlie (Aisha Tyler), who has only ever dated Nobel Prize winners. He and Rachel catch her and Joey kissing at the party.

Chandler and Monica undergo fertility testing and are surprised to encounter Janice. Chandler is afraid of ejaculating in a cup. Once they return, they find out that they can't get pregnant. Meanwhile, Rachel makes an appointment at a massage place. Phoebe tells her the place is horrible and rips up Rachel's certificate. Rachel tapes the certificate back together and goes to the massage place against Phoebe's wishes, but she doesn't know that Phoebe actually works there. In multiple attempts, Phoebe tries to act Swedish and Scottish but Rachel eventually finds out and convinces her to be true to herself. But Phoebe's greed for money gets the best of her and she doesn't quit. Joey needs help advancing in his relationship with Charlie, and turns to Ross for advice.

After learning they are reproductively incompatible, Chandler and Monica search for a sperm donor. After interviewing a suitable potential candidate (John Stamos), they decide to adopt instead. Phoebe realizes Rachel's feelings for Joey when she and Rachel take Charlie shopping, and Rachel fears Charlie heard that she likes Joey. Instead, Charlie believes that Phoebe likes Joey and thanks Rachel for convincing her not to make a move. While getting ready to go to Mike's sister's party, Phoebe meets David, the scientist guy, again and does not go to the party, instead going with him for dinner. Ross has an interview for a conference in Barbados.