Ross and Rachel experience the world’s worst hangover when they realize they’ve gotten married. Chandler and Monica back away from their own altar plans. Phoebe and Joey head back to New York in the taxi cab.
Monica and Chandler decide to move in together, leading Rachel to believe that all three of them will be roommates, and Monica doesn't want to tell her the truth. Meanwhile, Ross tries to keep Rachel from learning that their marriage hasn't been annulled.
Monica and Chandler disagree over how to redecorate Rachel's old room. Joey advertises for a "non-ugly" roommate. Ross is unwilling to accept that he still has feelings for Rachel.
Joey's health benefits lapse just as he develops a hernia. Ross is asked to give a lecture at NYU and eager to impress his students, he puts on a fake British accent. Meanwhile, Phoebe gets some bad news from her psychic.
Ross and Rachel try to get an annulment, but run into some legal obstacles. Joey finds keys to a Porsche in Central Perk and discovers some perks of being a fancy car owner. Meanwhile, Chandler, Monica and Phoebe babysit the triplets.
On the last night before Chandler and Monica move in together, Monica and Rachel argue, while Chandler tries to give Joey money to help him pay the upcoming bills.
Now roommates Phoebe and Rachel decide to start running together, but Rachel is embarrassed by Phoebe's odd running style. Joey finds a sexy new female roommate and tries very hard not to flirt with her. Meanwhile, Chandler decides to surprise Monica by cleaning the apartment, but forgets where everything goes. Ross tries to help him remedy the situation.
Ross goes too far while trying to impress a date by over-whitening his teeth. Rachel uses gossip to get her boss to like her after Phoebe supposedly makes out with Ralph Lauren. Meanwhile, Chandler convinces Joey that the changes Janine has introduced to their old apartment is making it too girly.
It's Thanksgiving and Monica's parents are coming to visit, which is a problem because, not only they do not like Chandler, they also don't know that he and Monica are living together. Rachel is tasked with making a Thanksgiving dessert, but she does so with mixed results. Meanwhile, Joey and Ross are eager to finish the dinner and leave, because they want to go to a Thanksgiving party with Janine and her dancer friends.
Janine gets an invitation to dance on "Dick Clark's New Year's Rockin' Eve" and she invites Joey, Monica and Ross to join her. Being huge fans of the show, Monica and Ross get overly excited. At the taping, Joey tries to kiss Janine at midnight and Monica and Ross resurrect their dance routine from high school. Meanwhile, Rachel, Phoebe and Chandler look for Monica's Christmas presents.
Rachel orders an apothecary table from Pottery Barn, which is a problem because Phoebe hates the mass-producing company. After Janine and Joey double date with Chandler and Monica, Janine tells Joey that she thinks the other two are boring. Ross buys a new apothecary table too, which causes problems for Rachel. After a confrontation with Monica and Chandler, Joey breaks up with Janine and she moves out.
After a joke gets published in Playboy, Chandler and Ross have an argument about who came up with it first. Meanwhile, a wayward remark of Phoebe's leads to trouble between the girls and a broke Joey starts working at Central Perk.
Joey gets in trouble for giving attractive female customers free food at Central Perk. A sick Monica desperately tries to convince Chandler that she's not sick. After her father cuts her off, Rachel's sister Jill comes to town. Rachel encourages her to start an independent life by finding a job and an apartment, but one thing leads to another and Jill ends up asking Ross out on a date. Even though Rachel doesn't want to admit it, she clearly isn't okay with that...
Chandler admits that he hasn't cried since he was a child. Phoebe discovers that Ursula is starring in porno movies using her name. Rachel desperately tries to stop Ross and Jill from starting a relationship.
Barry and Mindy's impending divorce prompts the gang to fantasize about what their lives might be like if they'd all taken different courses. Ross is still married to Carol, and Rachel is married to Barry, but fawning over famous soap star Joey Tribbiani. Monica is still fat and dating a doctor. Chandler is an aspiring writer and Phoebe is a Wall Street shark for Merrill Lynch. The gang continue to fantasize about how different their lives could have been. Carol and Ross decide to have a threesome to spice up their marriage. Rachel goes to Joey's but is incredibly nervous about cheating and gets drunk. Meanwhile, Monica's dinner date falls through and Chandler tries to cheer her up but things take an unexpected turn.
Joey tries to earn some extra money by entering a medical study, however, there's a slight problem: the study is for identical twins. Rachel and Phoebe take self-defense classes, but Ross attempts to give them a lesson in Unagi instead. Meanwhile, Chandler and Monica agree to give each other homemade presents for Valentine's Day.
At the end of semester Ross gets his student evaluations and one of them writes that he's hot. It turns out to be a cute girl named Elizabeth and even though it could cost him his job, Ross considers dating her. An ex-girlfriend of Chandler's from college is directing the new Al Pacino movie and Joey asks Chandler for help with getting an audition. Meanwhile, after a fire ruins Phoebe and Rachel's apartment, they're forced to find temporary living spaces with Monica and Joey.
After Joey's fridge breaks, he tries to cajole his friends into helping him buy a new one. Meanwhile, Ralph Lauren is organizing a charity ball and Rachel looks for a date, however, unexpectedly it turns into a competition between Monica & Chandler against Phoebe for finding the best candidate. Ross continues to date Elizabeth, but he gets nervous when she makes plans for a spring break at Daytona Beach.
Joey gets an audition for the lead character in a new TV show. When the audition is rescheduled, Chandler takes the message but forgets to tell Joey. When Joey misses the audition, he gets upset and the group reminisces about their mishaps in the past.
Ross meets Elizabeth's father for the first time and unfortunately he takes an instant disliking to Ross. However Paul does hit it off with Rachel and she tries to talk Ross up but does so with mixed results. Joey almost gets fired from "Mac and C.H.E.E.S.E." after offending the operator of the robot. Meanwhile, Phoebe writes a book based on Monica and Chandler.
While visiting an art museum, Monica puts her name on a two-year waiting list to use the museum for a wedding. Accidentally Chandler finds out about this and freaks out. Meanwhile, Paul threatens to have Ross fired from the university if he continues to date Elizabeth, however, that doesn't stop the two of them from going to her dad's mountain cabin over the weekend. Unfortunately for them, Paul has the same idea to bring Rachel there.
Chandler and Phoebe shop for a ring for Monica. Chandler finds the perfect one, but Phoebe accidentally lets it get away. While Chandler is busy with getting the ring back, Joey and Ross are lead to believe that he's mad at them, so they decide to team up and give him a cold shoulder treatment. Rachel continues to date Paul and wants him to open up to her, however, he opens up a bit too much.
Chandler plans to propose to Monica at dinner, but his plans go awry when Richard shows up at the same restaurant. Meanwhile, Phoebe and Joey join Rachel at a charity auction only to discover that Joey isn't aware what a silent auction is. And Ross and Elizabeth's relationship comes to a crossroad. Chandler continues to pretend to hate the idea of marriage, unaware that Richard wants Monica back. Meanwhile, Rachel and Phoebe discuss their 'back-up' plans, if they are not married by the time they're 40.
