Following their encounter the night before, Richard shows up at Monica's restaurant to tell her he's still in love with her and wants to marry her, children and all. Meanwhile, Chandler is continuing his deception that he doesn't believe in marriage to make his proposal to Monica a surprise. Rachel and Phoebe, jealous of Monica and Chandler's imminent betrothal, make pacts to have back-up guys in the event that they're still single by the time they're forty.moreless
Chandler plans to propose to Monica during a romantic dinner at her favorite restaurant, but his plans go awry when her ex-boyfriend Richard shows up. Phoebe and Joey agree to attend a Ralph Lauren silent charity auction with Rachel, particularly since there is an open bar. Joey ends up buying a sailboat. During a water-balloon fight at Elizabeth's, Ross becomes dramatically aware of their age difference, so breaks up with her. The gang, in thinking that Chandler has proposed, almost blows his secret, so he begins pretending he's against marriage in order to make his ultimate proposal a complete surprise.moreless
Chandler enlists Phoebe's help in picking out an engagement ring for Monica. Chandler finds the perfect one, but before he can actually pay for it, it is purchased by someone else. Chandler and Phoebe must now maneuver to get it back. Rachel wants Paul to share his feelings more, but regrets it when he finally opens up. In trying to hide his ring-shopping from the guys, Chandler leads Joey and Ross to believe that he's mad at them, so they choose each other as new best friends.moreless
While visiting an art museum, Monica puts her name on a two-year waiting list to use the museum as a setting for a possible future wedding to Chandler. When Paul threatens to have Ross fired if he doesn't stop seeing his daughter, Ross and Elizabeth take a trip up to her dad's cabin. Unfortunately, Paul has the same idea and shows up there with Rachel.moreless
Ross dreads meeting Elizabeth's father for the first time and asks his friends to talk him up, however, Rachel takes a much more personal interest in the guy. Phoebe is writing yet "another" book, this one featuring Monica and Chandler. Joey jeopardizes his role in the new TV series "Mac & C.H.E.E.S.E." when he disrespects his robotic co-star's creator and operator.moreless
Phoebe competes with Monica and Chandler to get Rachel a date for a charity ball. Joey's fridge is broken and he tries to cajole his friends into helping him buy a new one. Elizabeth tells Ross her intention to visit Daytona Beach for spring break which has him concerned.
Ross gets his student evaluations back and notes that a particularly attractive female student referred to him as "The hottie of the paleontology department". He ends up dating her, only to discover that it could cost him his job. A former college girlfriend of Chandler's is directing the new Al Pacino movie and Joey pleads with Chandler to get him an audition. Meanwhile, there is a fire in Phoebe's apartment, forcing her and Rachel to find temporary accommodations with Monica and Joey.moreless
Joey needs money for new headshots so tries to earn it by participating in a medical study. The problem is, the only study available requires that he be an identical twin. Rachel and Phoebe are taking a self-defence class. Ross scoffs at their claims that they can defend themselves against any attack, explaining that true self-defence requires "unagi". Chandler and Monica decide to give each other presents for Valentine's Day that they've made themselves.moreless
Carol and Ross haven't been having sex so Ross suggests spicing up their sex life by having a threesome. Carol is instantly onboard and invites her friend Susan into their bedroom. Rachel jumps at the chance to spend the night with soap star Joey Tribbiani, but drinks too much and throws up, instead. Fat Monica is nervous about consummating her relationship with her doctor boyfriend, so Chandler offers to sleep with her to show her the ropes. Phoebe has back-to-back heart attacks from the stress of losing millions as a stock broker.moreless
Barry and Mindy's impending divorce prompts the gang to fantasize about what things might have been like if their lives had 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.moreless
Joey gets in trouble for trying to pick up female customers at Central Perk by giving them free stuff. Monica is in denial about a bad cold she has and tries to seduce Chandler despite her condition. Rachel's father has taken back her sister Jill's credit card due to her reckless spending. He then tells her to go learn about the value of money from Rachel, the one daughter he's actually proud of.moreless
Chandler and Ross fight over the authorship of a joke that Ross had published in Playboy. A mindless remark by Phoebe leads to a squabble between her and the girls. Joey, now without a roommate or an income, is forced to take a job as a waiter at Central Perk.
After Rachel buys an apothecary table from Pottery Barn, she learns that Phoebe hates the mass-producing company. To avoid Phoebe's wrath, Rachel pretends she got it at a flea market. The deception escalates when Ross buys the exact same table. After Janine and Joey double date with Chandler and Monica, Janine tells Joey she thinks that Monica is too loud and Chandler is too boring and wants to see them as little as possible. When Chandler and Monica find out, it creates a rift between them, not to mention a real dilemma for Joey.moreless
Joey's feelings for Janine are growing stronger. When she gets an invitation to dance on "Dick Clark's New Year's Rockin' Eve", she invites Joey, Monica and Ross to be dancers, too. Joey sees it as the perfect opportunity to kiss Janine at "midnight". When Ross and Monica can't get enough camera-time at the taping, they decide to revive a middle-school dance routine that won them honorable mention in the brother-sister dance category. With Monica thus preoccupied, Rachel, Phoebe and Chandler try to grab a peek at the Christmas presents she bought them, following a frantic search.moreless
Monica's parents are invited to attend Thanksgiving at Monica's. Monica tries to avoid telling them that Chandler is living with her because her parent's dislike him. Rachel is charged with making dessert. When the pages of the recipe book get stuck together, she makes an English trifle that includes ingredients for shepherd's pie. Phoebe develops a crush on Mr. Geller. Joey and Ross try to hurry dinner so they can attend a Thanksgiving party with Joey's roommate Janine and her gorgeous dancer friends.moreless
Ross bleaches his teeth for a date with Monica's co-worker, but they end up being so insanely white, they now glow in the dark. Chandler convinces Joey that Janine is trying to take over his apartment by making it too feminine in décor. Phoebe makes out with the copy guy at Rachel's office thinking it's Ralph Lauren.moreless
Rachel and Phoebe decide to start running together, but Rachel, who runs like a sophisticated Manhattan jogger, is thrown off by the fact that Phoebe runs like a free-spirited little kid. Joey finds a gorgeous new female roommate. Chandler decides to surprise Monica by cleaning the apartment, but forgets where everything goes.moreless
Chandler and Monica are moving in with each other, which means Rachel is moving in with Phoebe and Joey will be without a roommate. Meanwhile, Ross doesn't want to help with packing so pretends to watch the Knicks' season-opener with Ben. Joey can't afford the apartment expenses with Chandler gone, so to help, Chandler tries to "lose" money to him in various games, including a card game he invents called "Cups".moreless
Joey finds the keys to a Porsche in Central Perk. When he is about to leave a note for its owner, he notices the positive attention it attracts, so instead, pretends it belongs to him. Phoebe agrees to let Rachel live at her place. Chandler, Monica, and Phoebe babysit Alice and Frank Jr.'s triplets. Unfortunately, no one is watching Chandler and he ends up having to go to the hospital. Ross and Rachel pursue an annulment, but discover they're going to have to get a divorce, instead.moreless
Ross is asked to give a series of lectures at NYU but is nervous about how he'll come across. He finds a colorful, albeit temporary solution to the problem. Phoebe learns from her psychic that she only has a week to live. Joey's health insurance has lapsed. When he develops a hernia, he has trouble auditioning for acting jobs, necessary for the restoration of his insurance. To her utter disbelief, Rachel finds out that she is still married to Ross.moreless
Monica and Chandler disagree over the best possible use for Rachel's old room. Joey advertises for a "non-ugly" female roommate. Ross denies that he is still in love with Rachel, but when Rachel needs a place to live after leaving Monica's, Ross suggests his apartment.
Monica and Chandler decide to move in together, leading Rachel to believe that all three of them will be roommates. When Monica finally explains to her that she'll have to move out, the fact that Rachel isn't the least bit upset, upsets Monica. Meanwhile, Ross lies to Rachel about having gotten the annulment.moreless
To their horror, Ross and Rachel discover that while drunk the previous night, they got married. Ross resists the idea of annulment, however, since it would mean a third failed marriage. After witnessing the disaster of Ross and Rachel's wedding, Chandler and Monica reconsider their own plans to marry and decide to let fate make the decision for them. The problem is, the signs seem to keep pushing them back to the altar. Phoebe and Joey head back to New York in the taxi Phoebe loaned him, but Joey proves to be less than a fun travel companion.moreless