The gang celebrate Monica and Chandler's engagement. Phoebe wants to be the musician at the wedding and comes up with a new song, while Joey tries to dress and act like a 19-year-old for an audition. Ross and Rachel briefly reunite and after Monica catches them kissing, she's convinced that Rachel is trying to steal her thunder.
As Monica starts planning her wedding she's shocked to find out that her parents have spent her entire wedding fund. However, her spirits are restored when she discovers that Chandler has enough savings for her dream wedding scenario. Phoebe temporarily moves into Ross's apartment, bringing her massage clients with her. This leads to some weird encounters for Ross. Meanwhile, Joey mocks Rachel when he finds an erotic novel she is reading.
Monica tries to figure out Phoebe's grandmother's secret chocolate chip cookie recipe. Meanwhile, Rachel tries to teach Joey how to sail, and Chandler has an awkward encounter when he tries to bond with Monica's father.
While hiring a new assistant, Rachel is torn between hiring a much more qualified woman, or a handsome but inexperienced young man. Monica, Chandler and Ross engage in a war of secret sharing after Monica and Chandler vow to be more honest. Meanwhile, Joey has problems when his TV show is cancelled after just one airing.
While taking an engagement picture for himself and Monica, Chandler cannot make anything but a weird face. Meanwhile, Rachel enlists Joey to take Tag out for a night on the town. Also, Phoebe and Ross date a couple in the middle of a divorce.
Joey and Ross accidentally take a nap together - and much to their dismay, find that they liked it. Phoebe and Rachel compete to become Monica's maid of honor.
Rachel and Phoebe befriend a girl Joey's dating and they try to convince him to get more serious with her, however he's reluctant to do so. At least at first. Meanwhile, Ross discovers that his doctoral dissertation is hosted at university's library and is very excited about the fact. Unfortunately, he soon finds out that students aren't exactly reading it, but rather engaging in other 'physical activities' in the paleontology section. Also, Monica runs into Janice and before she knows it, Janice has invited herself to Monica's wedding. Needless to say that neither she nor Chandler are exactly ecstatic about it and they both try to find a way to tactfully uninvite her.
Ross drives himself insane when he can't name all 50 states in a simple game. Tag joins the gang for Thanksgiving dinner, where Joey accidentally spills the beans about Rachel's crush on him. Phoebe sneaks a dog into the apartment, making Chandler extremely nervous.
When Phoebe tells the gang about how she was too poor to have a bike as a child, Ross goes out and buys her one. While Phoebe absolutely loves the bike, the gang soon discovers that she doesn't actually know how to ride one. Meanwhile, Monica decides to make candy in order to get to know her neighbours, and while they all love the candy, nobody is particularly interested in Monica herself. Rachel and Tag try to hide their relationship at work, but things go awry when Rachel writes a playful work evaluation of Tag that he accidentally turns in to Human Resources.
Ross's plans to teach Ben about Hanukkah are continually thwarted when the young boy can't get his mind off of Santa. Meanwhile, Phoebe prepares to move back into her refurbished apartment, with or without Rachel. However, she'll stop at nothing to get Rachel to go with her, including buying Joey a drum set. Monica is mystified by Chandler's inability to tip properly.
Phoebe gets upset with Joey when he blows off dinner with her for a date, however only a few days later she finds herself in the same situation but with their roles reversed. Meanwhile, Chandler and Rachel enjoy a cheesecake that gets delivered to their address by accident. They feel guilt-ridden at first, but it's just too delicious. Also, Ross and Monica attend a wedding reception of their cousin and find themselves in an awkward situation.
After the gang head up to the roof to see a passing comet, separate events unfold that lead to them all having a sleepless night.
Rachel accidentally breaks Joey's armchair (that he's named Rosita) and while they're out shopping for a new one, it appears that Rosita has magically "healed" herself. Meanwhile, Phoebe takes a temp job as a telemarketer for an office supply company and when her first client turns out to be suicidal, she goes out of her way to talk him out of it. Also, Ross and Monica find out that their parents are selling their childhood home.
When Rachel turns 30, the gang reminisces about their 30th birthdays. Ross buys a sports car to look cool, Monica gets drunk, and Phoebe, while trying to patch things up with Ursula, discovers that she is actually 31.
Joey's character on Days of Our Lives is awakened from his coma with a brain transplant from one of the show's most legendary characters. Ross practices the bagpipes for Monica and Chandler's wedding. Meanwhile, Phoebe and Rachel fight over a guy who left his cell phone in Central Perk.
Chandler is shocked to find out who Monica really wanted to sleep with the night they first got together in London. Meanwhile, Rachel gets into trouble with Ross when she teaches Ben practical jokes.
Monica regrets telling a woman about a discount bridal shop when they end up fighting over the same dress. Meanwhile, Joey and Ross discover that they're dating the same girl.
Joey is nominated for a Soapie Award for his part on Days of Our Lives, and while he doesn't win, he ends up with an award anyway - together with his partner in crime, Rachel. Meanwhile, Ross finds himself in an awkward position when one of his students proclaims that he failed his midterm because he's in love with Ross. Also, Monica freaks out a little when she realizes that after marrying Chandler she's not gonna experience a rush of dating someone new ever again. In a surprising change of roles, Chandler becomes a voice of reason that calms her.
Joey auditions for a big movie role which will require him to appear naked. A problem arises, however, when the part calls for an uncircumcised man. Meanwhile, Rachel and Phoebe go through the trouble of organizing a last minute bridal shower for Monica. And Ross becomes attracted to his cousin after she visits.
At Central Perk Rachel runs into her friend from college, Melissa, and it turns out they share something more than just a friendship. Meanwhile, Monica plans the seating arrangement for the wedding and is taken by surprise when Joey mentions that his parents are coming to the wedding too. Also, Chandler and Ross argue who gets to wear a celebrity tux for the event.
Monica and Chandler are getting married in four weeks and have to write their vows, but neither has a clue what to say, so they reflect on their past. In the end, the only real problem is who will be saying the vows first.
When Monica's Porsche shows up again, Ross and Rachel hit the freeway together and it turns out to be an adventurous ride. Meanwhile, Chandler and Monica go off to Vegas to find Chandler's estranged father. And back at home, Joey proves his masculinity to Phoebe.
So close to the wedding, Chandler suddenly realizes the overwhelming meaning of getting married and takes off without warning anyone. Meanwhile, Joey acts opposite a famous actor in a movie, but can't bring himself to tell him that he spits when he says his lines. Phoebe and Ross try to find Chandler before the wedding starts, while Rachel tries to hinder Monica, so that she doesn't find out the shocking news. On the day of the wedding Joey encounters a scheduling problem, while Phoebe and Rachel come across a surprising discovery.
