Ross and Rachel wake up in bed together, remembering almost nothing about the night before. At breakfast, their friends ask them about it. Shocked, they decide to get an annulment once they're back in New York. Ross tells Rachel he's taken care of it, but he hasn't. Neither Chandler nor Monica wants to go through with their own marriage plans, but each one is scared to back out. They decide to look for another sign... but even though the signs keep coming, they keep denying it. Finally, Chandler suggests they live together. Joey (who still has Phoebe's cab) convinces her to keep him company on the drive home. He promises to make it a fun road trip, but he ends up sleeping most the time.

Ross hasn't gotten the annulment yet... but he has gotten a little crazy. It seems the idea of a 3rd failed marriage has pushed him over the deep end. Phoebe (and her panel of women) decide Ross is still in love with Rachel. Ross is in such denial about this that to prove them wrong he goes to his lawyer (Russell) to take care of the annulment... but finds that it's more complicated than expected, and Rachel will have to be told the truth. Chandler and Monica break the news of their live-in plans, first with Joey (who is happy for them, but sad to be losing Chandler) and then to Rachel (who doesn't seem to have much of a reaction at all... until she takes it seriously). Rachel is so sad that Ross still can't tell her the truth. Phoebe foretells the future marriages of the entire group.

When Rachels asks if she can live with Phoebe, Phoebe claims to have a roommate named Denise. Rachel tries to find a new apartment, and receives offers from Joey and Ross. Ross goes back and forth on whether he thinks it's really a good idea. Phoebe continues telling Ross he's in love with Rachel, and he keeps denying it. Chandler and Monica fight about what to do with Rachel's room and Chandler's furniture. For a while it looks like no one will be moving anywhere. Joey searches for a new roommate, and it's clear what he's really looking for. Ross still doesn't tell Rachel that they're still married.

Rachel packs her things and moves to Ross's apartment. Once there, she intercepts a phone call from Ross's lawyer revealing they're still married. Phoebe's psychic tells her she's going to die this week. Ross becomes a guest lecturer at NYU. He's so worried his presentation won't go well that he panics and presents it with an phony English accent. Joey's medical benefits lapse because he hasn't done enough acting recently. He contacts his agent, Estelle (who mistakenly believes he'd gone to another agent), to arrange for some auditions. He gets a severe hernia before auditioning, but refuses to go to the hospital until he has insurance again.

Rachel and Ross go to a judge to get their annulment, but they air too much dirty laundry. The judge decides they don't qualify for an annulment, so they go to Ross's lawyer for a divorce. Ross makes it pretty obvious that he still loves Rachel. Rachel reveals that it was her drunken idea to get married. Joey finds the keys to someone's Porsche. He decides to wait by the car until the owner shows up. He gets mistaken for the owner, and likes the attention he gets so much that even after the owner takes the car away, he keeps up the charade. Phoebe, Monica and Chandler take care of Frank and Alice's babies. Chandler gets a toy stuck in his throat and Monica takes him to the doctor. Phoebe has to take care of the babies by herself.

Chandler tries to get Joey to accept some money so he'll be able to get by for a few months without a roommate. Joey won't take it, but Chandler invents a game called "Cups" and lets Joey win the money. Later, Joey teaches Ross to play Cups, and loses all the money to him. While packing on Rachel's last night in the apartment, Phoebe's misguided advice leads Monica and Rachel to fighting. Ross doesn't want to help with the packing, so he says he has to take care of Ben. Since Monica can see into his apartment, he makes a "fake Ben" to fool her.

Rachel and Phoebe, new roommates, decide to run together in the park each day. Phoebe's weird running style embarrasses Rachel. Joey gets a beautiful new roommate (Janine) and struggles to avoid flirting with her. He thinks she's interested in him, so he seeks advice from Ross and Chandler on how they "repel women." Chandler cleans his and Monica's apartment, but afterwards can't remember where everything goes. He tries to keep Monica out of the apartment while he figures out what to do.

Phoebe visits Rachel at work and makes out with Kenny the copy boy, thinking it's Ralph Lauren. She tells Rachel, who gossips to her boss (Kim), who eventually becomes convinced that Rachel is having an affair with Ralph Lauren in order to get Kim's job. Ross goes too far when he whitens his teeth in preparation for a date with Hillary, Monica's co-worker. Chandler tries to convince Joey that he's letting Janine make him and the apartment too girly.

For Thanksgiving, Janine invites Joey and Ross to hang out with her and her dancer friends, but they have to eat dinner at Monica's first. Mr. and Mrs. Geller come over as well, and Chandler finds out they don't like him because they think he does drugs; Ross once told them Chandler was smoking pot, in order to cover his own guilt; Monica reveals the truth, which leads to many more revelations. Rachel makes an English Trifle for dessert, but gets the recipe mixed up with a Shepard's Pie. Phoebe dreams about Mr. Geller and starts to see him differently... until another dream ends it for her.

Janine gets highered to dance at the pre-taping of Dick Clark's New Year's Rockin' Eve; she invites Joey, Monica, and Ross to come along. This is a dream come true for Ross and Monica, but they have a hard time getting on camera, because they aren't as good as they think they are. Joey hopes to kiss Janine at "fake midnight." Rachel and Phoebe convince Chandler to help them search for the Christmas presents Monica is giving them.

Rachel buys furniture from Pottery Barn, but tells Phoebe she got it at a flea market, because Phoebe hates Pottery Barn. The deception is complicated by the fact that Ross buys an identical table from Pottery Barn. Joey and Janine spend time with Monica and Chandler; Janine doesn't like hanging out with them, and hard feelings grow and grow until Joey and Janine break up and Janine moves out.

Ross gets a joke published in Playboy, but Chandler claims it's his. The girls are curious and peruse the Playboy to check out the women, and get into a discussion of which one of the three each would chose to date if they had to pick. Phoebe choses Rachel, which leads to competition and hurt feelings. Joey's cable and phone are disconnected because he couldn't pay. He takes a job as a waiter at the coffee house to earn some extra money. After closing the shop for an hour so he can go to an audition, he is fired. But Rachel tells Gunther to give Joey his job back, and of course Gunther complies.

Joey gives all the pretty female customers free stuff at the coffee house, in order to get dates with them. Monica is sick and won't admit it. She tries to get Chandler interested in sex, but he's put off by her illness. Rachel's sister, Jill, shows up because she's been financially cut off and has to try to make it on her own. Rachel's worried that there's something developing between Ross and Jill, but somehow ends up actually encouraging Jill to ask Ross out.

Unable to handle the idea of Ross and Jill together, Rachel asks Ross to stop seeing Jill. Jill is upset and throws herself at Ross, attempting to use him to get back at Rachel. Chandler doesn't cry in sad movies... or for any other reason. The gang discovers that Ursula is making porn movies in Phoebe's name.

News that Barry and Mindy are getting divorced gets the gang wondering what their lives would be like if Rachel married Barry; if Ross's wife Carol hadn't realized she was a lesbian; if Monica was still fat; if Joey was still on Days of Our Lifes; if Chandler had quit his data entry job to pursue writing; and if Phoebe was a stock broker: Ross and Rachel, both in unhappy marriages, run into each other on the street after not seeing each other for years. Ross brings Rachel to Central Perk to see Monica; Rachel quickly swoons over Joey, aka Dr. Drake Ramoray. Monica is dating the very boring Dr. Roger. Chandler is unemployed, but takes a job as Joey's assistant, which doesn't work out very well; but he is inspired by the experience and sells his first story to Archie Comics. Phoebe is ruthless and greedy, and has a heart attack after losing 13 million dollars on the stock market. While she's in the hospital, Ross finds out she's fired, but he doesn't dare tell her, fearing it will cause another heart attack. Ross suggests to Carol that they spice up their non-existant sex life. Carol doesn't like any of his ideas... except having a threesome. Rachel decides to have a fling with Joey. Monica reveals she's still a virgin.

In the continuation of the alternate reality: Ross and Carol have a threesome with Susan, but Ross feels left out. Phoebe goes stir-crazy in the hospital, and sneaks back to work, only to find our she's been fired, and promptly has another heart attack. Rachel spends the evening at Joey's, but gets drunk and sick, and passes out. Monica decides it's time to have sex with Dr. Roger, but he gets paged and leaves. Chandler and Monica decide to have a one-night stand, but afterwards Chandler convinces her to dump the doctor and be with him. Rachel, relieved that she didn't cheat on Barry, returns home and find Barry in bed with another woman... their neighbor's dog walker. She returns to the city to hook back up with Joey, but runs into Ross. They console each other on their bad marriages and Rachel helps Ross realize that Carol is a lesbian. Phoebe goes back to singing at the coffee house.

Joey's financial needs aren't being met by his job at the coffee house, so he looks into participating in another medical study. The only one available is for identical twins, but it pays so much that Joey can't resist. He hires another actor to play his twin brother. Rachel and Phoebe are taking a self-defense class, but Ross feels they don't have Unagi, a state of total awareness, in which you can be prepared for any danger. He startles them in the hallway to prove his point, which sets off an on-going competition of psuedo-attacks. Chandler and Monica plan to celebrate Valentines day (late) by making gifts for each other. Chandler can't make anything and Monica forgets until the last minute. Chandler gives Monica a customized tape of music which actually was a previous gift from Janice; Monica give him a sock puppet that Phoebe made.

Flattery in a teacher evaluation leads to Ross dating one of his students (Elizabeth). He finds out he could get fired, but the forbidden nature of the relationship makes Elizabeth want it even more. An old friend of Chandler's (Dana) is Directing an Al Pacino movie, and Joey asks Chandler to get him an audition. Monica is jealous of the time Chandler spends with Dana. A fire in Phoebe and Rachel's apartment means they'll have to stay with their friends for a few weeks--one at Monica's and one at Joey's. At first Monica's apartment seems to be the accomodation of choice, but it soon becomes clear that Joey's is the place to be.

Joey's refrigerator breaks down, so he tries to manipulate his friends into paying for part of it. Plus he has to eat all those perishables by himself. Rachel is looking for a date to a charity ball; Phoebe finds a guy for her, but so do Monica and Chandler; things get competitive. Ross and Elizabeth continue their "secret" romance. When Elizabeth announces she's going away for Spring Break, Ross misunderstands and thinks she's asking him to go with her. When he finds out she's going away without him, he starts to worry about how much "partying" she might be planning.

Joey auditions for a new TV show and makes the call-back list; but when the call-back time gets changed, Chandler neglects to give Joey the message. Chandler has a chance to redeem himself when he takes a message that the part is available again. Phoebe and Ross help Joey run his lines, and they become convinced that they're great actors. Monica doesn't like the chick and the duck. We see flashbacks to earlier episodes demonstrating: Joey's acting; the pressure everyone feels at work; Chandler's mistakes; Joey's mistakes; friends fighting and making up; Chandler and Joey hugging.

Joey doesn't get along well with the roboticist (Wayne) who controls his co-star, "C.H.E.E.S.E." To save himself from being fired, he teaches Wayne how to talk with women. Phoebe writes a book about relationships, which is really a book about Monica and Chandler, and everything they do. Ross meets Elizabeth's dad (Paul), who really doesn't approve of his daughter dating an older man. Paul and Rachel start dating. The gang's attempts to make Ross look good for Paul continually backfire.

Monica, not yet engaged, gets on a two-year waiting list to hold a wedding at a local museum; however, due to a cancellation, the museum calls and offers her a spot sooner, to Chandler's surprise. He freaks out... or so it seems. Paul tells Ross to stop dating Elizabeth; Ross and Elizabeth go away for a secret weekend at her grandmother's cabin, but Paul and Rachel show up there as well. Ross gets away with it, thanks to some emotional blackmail. Joey, back in show businees, tries to get his celebrity picture back on a dry cleaner's wall. Gunther realizes Joey's not working at the coffee house any more.

Chandler picks out an engagement ring for Monica, with Phoebe's help. Unfortunately, someone else buys the ring before Chandler has a chance to. He has to convince the other buyer to trade rings with him. Meanwhile, Joey and Ross are feeling brushed-off because Chandler isn't hanging out with them. Phoebe makes matters worse by suggesting that Chandler is angry with them. Rachel tries to get Paul to open up and express his feelings. She gets more than she expects and can't turn it off... so she dumps him.

Everyone except Monica knows that Chandler is about to propose. He plans to do it at Monica's favorite restaurant, but they bump into Richard there, which derails his plans. Returning home, the rest of the gang almost blows the secret, and Chandler decides to act like marriage is the furthest thing from his mind, so Monica won't get suspicious. Rachel takes Phoebe and Joey to a charity event which her boss is hosting. Phoebe drinks a lot; Joey thinks the silent auction is just a contest to guess the right price, and he ends up buying a sailboat for $20,000. Rachel convinces the second-place bidder to buy it, but she also convinces Joey to keep it, in the process. A dorm-room water-balloon fight shows Ross that his relationship with Elizabeth doesn't have a future, so he breaks up with her.

To make his eventual proposal a surprise, Chandler begins his campaign to convince Monica he never wants to get married. Richard shows up at Monica's restaurant and tells her he still loves her, leading Monica struggling with what she wants for her future. Joey hangs out in his new Captain's outfit. Rachel and Phoebe talk about having backups: guys to marry if they're not married by the time they're 40. Rachel tries to line up Ross as a backup, but discovers Phoebe has already made that deal with Ross... and with Joey, too. The four of them have a confrontation and decide that Ross is Rachel's backup, and Joey is Phoebe's. Chandler and Monica finally get engaged.