Iedereen is verward door wie Rachel ten huwelijk is gevraagd. De situatie wordt nog complexer nadat Phoebe met Rachel heeft gepraat, waardoor ze ten onrechte denkt dat Ross haar verloofde is.

Joey's vergeefse pogingen om Ross zijn vergiffenis te winnen omdat Joey per ongeluk Rachel heeft gevraagd om met hem te trouwen, resulteert enkel in een spoedopname in het ziekenhuis.

Ross is niet blij wanneer Rachel voorstelt om de dokter uit zijn kindertijd als nieuwe kinderarts van Emma te vragen. Ondertussen besluiten Phoebe en Joey om een partner voor elkaar te regelen voor een double-date.

Phoebe is bang om haar laatste vriend Mike te verliezen. Haar zelfvertrouwen neemt nog meer af door de domme opmerkingen van Ross. Chandler zit in Tulsa, Oklahoma, voor een opdracht.

Ross is niet blij met Emma's nieuwe gevoelige oppas. Phoebe moet kiezen tussen twee hartstochtelijke vrijers. Chandler voelt zich bedreigd wanneer Monica vertelt over een van haar nieuwe grappige collega's.

Chandler kan zijn behoefte niet bedwingen om Joey te vergezellen wanneer Joey het appartment van Monica's ex-vriend Richard gaat bekijken. Maar ze krijgen nog meer te zien dan waarop ze gerekend hadden, ze ontdekken een oude videoband met Monica in de hoofdrol terwijl ze de liefde bedrijft...

Rachel's egoistische zus verpest het Thanksgiving-diner met haar ongecensureerde opmerkingen. Monica beschermt overdreven haar porseleinen huwelijksservies en Joey vergeet om zijn mede televisieacteurs te vergezellen in de Thanksgiving parade.

Joey becomes convinced that Monica is having an affair, after Chandler sneaks back into town without him knowing, in order to have some alone time with his wife. Meanwhile, Rachel and Phoebe have a girls night out, and Rachel gives her phone number to a guy they meet at a bar. Also, Ross and Mike try to hang out together but it doesn't go very well, since they can't find a common interest to talk about.

Everyone in the gang gets a little upset when Chandler announces that he'll be spending Christmas and New Year's Eve in Tulsa because of work. To make matters worse, Monica gets quite jealous when she finds out that one of Chandler's co-workers is a former Miss Oklahoma runner-up. After doing some retrospection, Chandler decides to quit his job.

Chandler starts looking for a job and is anxious about having a baby with Monica while uncertain about his career prospects. Meanwhile, Rachel visits work and finds out that during her leave, a guy named Gavin has been temporarily assigned to take care of her job. She starts to feel insecure about her job position and decides to come back from her leave early. Also, Phoebe works as an extra on Joey's TV show and brings even more drama to the set.

Gavin gives Rachel a very interesting birthday gift while Ross begs Joey to stay away from Emma's hot new nanny. Meanwhile, Mike meets and then accidentally murders Phoebe's unusual pet.

A night at Mike's piano bar gives Monica a very showy moment in the spotlight. Ross struggles to move on after witnessing Gavin and Rachel kiss. Meanwhile, Chandler employs his secret skill to repair Joey's botched eyebrow-waxing job.

Phoebe and Joey purposely set Ross and Rachel up on bad dates in the hopes they'll get back together. Meanwhile, Monica and Chandler babysit Emma, and aren't being as responsible as they should be.

Joey endures a draining audition at the hands of a pompous actor-director. Ross and Phoebe discover a secret link after being mugged together on the street. Chandler's advertising internship gets off to an impressive start.

While reviewing their monthly expenses, Monica and Chandler discover that their situation is less than stellar. This results in Monica asking Joey to lend her some money without telling Chandler. When Chandler eventually finds out, Joey comes up with a lie that Monica needs the money for breast enhancement procedure. Meanwhile, Phoebe gets really excited as she and Mike decide to move in together, but her excitement quickly dissipates once she discovers that Mike doesn't see himself getting married ever again. Also, Rachel's attempt to baby-proof the apartment tampers with a frustrated Joey's sanity.

Chandler's jokey entry on his and Ross's college website leads to a faux burial service for the allegedly dead and obviously unpopular Gellar. Meanwhile, Joey is unwilling to give his favorite stuffed animal, Hugsy, to Emma. And Phoebe asks Monica to help her avoid a post-breakup tryst with Mike.

Monica leads the gang, except for a scoffing Ross, to purchase a bunch of lottery tickets for the multi-million-dollar powerball jackpot. However, as they gleefully plot about how they will spend the fortune if they win, they start bickering among themselves until Phoebe takes matters into her own hands. Meanwhile, Chandler frets as he waits for a phone call about a hiring job position and Rachel thinks baby Emma is close to saying her first words.

After visiting the set of "Days of Our Lives", Rachel catches herself dreaming about a romantic encounter with Joey. Meanwhile, Chandler buys a non-refundable weekend getaway for himself and Monica, but when she can't get time off at work, Ross joins him. Also, Phoebe takes advantage of Monica's restaurant clientele.

Joey secretly throws a party on the roof of his building for the "Days of Our Lives" cast and he reluctantly invites the rest of the gang, once they discover his plans. Meanwhile, Ross meets a new colleague, Charlie, and is instantly attracted to her, however, he feels intimidated once he learns about her accomplished ex-boyfriends. Also, everyone forgets to tell Chandler about the change of plans and he gets stuck at a theater play by himself.

Joey comes to Ross for advice on dating Charlie, since they don't share much of the same interests. Meanwhile, Chandler and Monica bump into Janice at a fertility clinic. Also, Rachel has a gift certificate for a massage at a fancy massage place which Phoebe doesn't want her to use, since she doesn't approve of big corporations.

Rachel and Phoebe take Joey's girlfriend Charlie shopping, where she overhears the two of them gossiping about Joey. Meanwhile, Ross gives a presentation to a fellow professor in the hopes of getting the role of keynote speaker at the paleontology convention in Barbados. Also, Monica and Chandler consider alternate pregnancy options making some people really uncomfortable in the process.

The gang heads down to Barbados for the paleontology conference. While Ross and Charlie are excited about attending multiple seminars, the rest of the gang just want to enjoy their time on the beach but the rainy weather prevents them from doing so. Things, however, are far from boring - Phoebe discovers that she still has feelings for Mike even though she enjoys spending time with David, Rachel feels lonely and struggles to keep her feelings about Joey to herself, and Chandler is amused by Monica's hair.