Beginning moments after Chandler proposes to Monica, the hip and hilarious antics of TV's favorite friends follow as Chandler (unsuccessfully) tries to bond with his future father-in-law; Rachel gets a hunky assistant and Ross introduces his son to the miracle of Chanukah by way of the Holiday Armadillo.
The gang celebrates Monica's engagement night. Rachel, feeling lonely, kisses Ross (and considers doing more). Everyone thinks it's a big deal and Monica accuses Rachel of stealing her thunder. Phoebe asks if she can play at the wedding, and won't let up until she's convinced they'll really let her. Joey prepares to audition to play the part of a 19-year-old. Phoebe eats Joey's candy bar. Chandler is unable to perform in the bedroom.
Monica begins to make wedding plans with Rachel's help; Chandler feels left out. Phoebe wants to give Monica and Chandler some time alone, so she moves in with Ross for a couple days. But Ross is not happy with her running the massage business from his apartment. While Phoebe is out, he agrees to give a massage, thinking the client is a beautiful young woman, but it turns out to be her old, overweight father. The duck gets sick after eating Rachel's face cream. Chandler and Monica find out that Mr. and Mrs. Geller have spent Monica's wedding fund. Chandler has enough savings to cover it, but isn't sure that's the way he wants to use the money. Joey finds an erotic book that Rachel's been reading, and won't let her live it down.
Joey's TV show (Mac and C.H.E.E.S.E.) premiers. He gets called in to audition for the part of Stryker Ramoray (Drake's twin brother) on Days of Our Lives. But his new-found stardom goes to his head and he walks out. Since his TV show stinks, it gets cancelled and he has to come crawling back to Days. Rachel hires an assistant, and choses a pretty-boy (Tag) instead of a qualified woman. Monica and Chandler decide they shouldn't have secrets from each other, but it backfires on upsets them both, and Ross as well.
Monica and Chandler try to get a good engagement picture, but it seems impossible because Chandler can't seem to smile properly when there's a camera involved. Phoebe and Ross date a couple who're getting divorced. They constantly argue about their dates' bad qualities. Ross ponders starting a divorced men's club. Rachel arranges for her assistant, Tag, to spend time with Joey, so he can't go out with women at the store. But Joey hooks him up with lot of women. Joey keeps staining his shirts.
Monica tells Rachel and Phoebe to decide who is going to be her Maid of Honor. They can't come to an agreement, so Joey and Ross hold "auditions" for the part. Someone overhears that Monica is marrying Chandler, and wishes a sarcastic "good luck." She turns out to be Julie Graff, whom Chandler dumped when he was 15 because she got fat. Monica convinces him to apologize to her. After watching Die Hard, Ross and Joey fall asleep on the couch and have a very good nap. At first they are very upset that it happened, but eventually they decide to try it again.
Joey has a one night stand and wants Rachel to dump the girl (Erin) for him. Not only can't Rachel do it, but she and Phoebe become friends with Erin and arrange for Joey to go out with her again. Joey decides he really likes Erin, but Erin decides there isn't a future in the relationship. Ross discovers that his Doctoral Thesis is in NYU's library. When he goes to visit it, he finds that it's in a remote corner frequented by couples engaging in sexual activities. He begins to patrol that area of the library, but ends up being a culprit himself. Monica runs into Janice, who invites herself to Monica and Chandler's wedding.
The gang all play a game where they have to try to list all 50 states; Ross gets so involved in it that he misses Thanksgiving dinner. Chandler and Monica find out that Phoebe is keeping a dog in the apartment; Chandler reveals his fear of dogs. Rachel invites Tag over for Thanksgiving dinner. He's depressed because he and his girlfriend just broke up. Rachel tries to decide whether to comfort him as a friend, or to make a move. She decides to just be a friend, but Joey lets the secret slip out.
Ben's first "big kid's bike" prompts Phoebe to reveal that she's never had a bike of her own; Ross gives her one as a gift. However, it soon becomes clear that Phoebe has never learned to ride. Monica decides to get to know her neighbors better by making candy for them; it becomes so popular that she can't keep up with the mob waiting outside her door for more. At work, Rachel writes a joke evaluation of Tag, full of sexual comments, which accidentally gets sent to the Human Resources department.
Ross has his son, Ben, for the holidays and decides to teach him about Hanukkah. Ben can't handle the idea of no visit from Santa, so Ross tries at the last minute to find a Santa costume. The rental shop is all out so he rents an Armadillo costume instead. Things go from bad to worse but in the end he finally gets to give Ben Hanukkah and Christmas. Phoebe's apartment in finally done being rebuilt after the fire. Worried that Rachel won't want to move back in with her, she tries to rive a wedge between Joey and Rachel by giving Joey a drumset and a tarantula. It backfires, but Rachel wants to live with Phoebe anyway. The apartment looks great but no longer has two separate bedrooms. Phoebe likes the spaciousness, so Rachels keeps living with Joey. Chandler tries to master the art of smoothing slipping someone money during a handshake.
Chandler and Rachel can't stop eating someone else's cheesecakes, which are mistakenly delivered to Chandler's apartment. Monica is upset that she wasn't invited to her cousin's wedding, but the rest of her family was. Phoebe chews out Joey for cancelling their plans together so he can go on a date; then she does the same to him when her old flame David (Scientist Guy) shows up in town for a day.
After watching for a comet on the roof of their building, the gang goes their separate ways; but all end up staying up all night. Joey and Ross get stuck on the roof and spend the night trying to get down. Rachel and Tag spend the night trying to find some important documents that were supposed to get sent earlier that day. Phoebe is kept awake by the smoke alarm that won't die. Monica and Chandler can't get to sleep and spend the night reading, talking, coupling, and cleaning.
Rachel breaks Joey's chair (Rosita) so she buys him a new one; meanwhile Chandler thinks he broke it, so he replaces it with his own identical chair. Joey believes the chair miraculously healed itself, so Rachels keeps the new chair. But Joey is jealous, so he breaks "his" chair so he can have Rachel's. Mr. and Mrs. Geller are selling their home so Ross and Monica go to pick up their childhood things. Ross's are fine, but Monica's have been ruined by flood water. To make it up to her, Mr. Geller gives her his Porsche. Phoebe takes a job as a telemarketer and her first contact (Earl) doesn't want to buy anything because he's planning to kill himself. Phoebe convinces him to keep living.
Rachel's struggles with turning thirty prompt the rest of the gang to remember they're thirtieth birthdays. Monica got drunk just before her surprise party; Phoebe tried to reconcile with Ursula and found out she was actually 31; Ross bought a sportscar, but couldn't get it out of it's parking spot; Chandler just turned 30; Joey cried and blamed God. Rachel decides that in order to accomplish her goals in life, she needs to find the man she's going to marry. So she breaks up with Tag.
While arranging the wedding, Monica and Chandler learn that Ross has a surprise in store: He's planning to play the bagpipes. His playing leaves much to be desired. Joey's comatose character on Days of Our Lives gets a brain transplant from the dying star, so he goes to her for advice. Rachel and Phoebe find a cell phone left behind by a cute guy, and wait for him to call so they can make a date with him. Unfortunately, the cell phone really belongs to the cute guy's elderly boss.
Rachel watches Ben while Ross has a meeting, and she teaches him all about practical jokes. Ross doesn't like it, but he eventually turns the tables on Rachel. Chandler and Monica try to find a minister for their wedding, but don't like their options. They decide to let Joey (who's being ordained over the Internet) perform the ceremony. Monica gives Phoebe some pills for her headache. When Phoebe finds out about the possible side-effects, she fears the worst. While discussing how they first got together in London, Chandler finds out that on the fateful night when Monica first came to his hotel room, she had been planning to hook up with Joey. Phoebe can't help wondering what things would have been like if Joey and Monica ended up together, prompting an alternate-storyline flash-forward of Monica cooking lots of fried food for a very fat Joey.
While searching for the right wedding dress, Monica meets Megan, another woman engaged to be married. Monica tells her about a great wedding dress sale the next day. Not only do they both go to the sale, they both grab the same gown. After a brief struggle, Monica previals. However, Megan books the band the Monica and Chandler want for their wedding, and blackmails Monica into returning the dress. Ross and Joey both meet and begin dating a pretty woman who is moving into the neigborhood. Once they find out that they're both dating the same woman, the competition gets fierce. Chandler, Ross, and Joey give themselves facials for their T-zones.
Joey gets nominated for a "Soapie" award for his return as Drake Ramoray in Days of Our Lives. He loses, but he steals a trophy from one of his costars (Jessica) who doesn't appreciate it. Rachel, Phoebe, and Joey practice receiving awards. Ross makes Dinosaur sounds for his class. A male student (Ned) reveals he's in love with Ross, claiming that's why he's doing so poorly in class. Ross sympathizes and decides to change Ned's grade for the better, until he finds out it's just a scam. Phoebe's new romance with Jake makes Monica realize that once she's married, she'll never have another "first kiss" or be with anyone else.
Joey is up for a leading role in a movie, but the director is looking for an uncircumcized male to do a nude scene. Joey claims he's not circumcized, and then Monica helps him by making a variety of attachments to choose from. (He chooses Silly Putty.) But the piece falls off during Joey's final audition. Rachel and Phoebe realize they're expected to throw Monica a bridal shower, so they quickly put one together. Ross and Monica's cousin Cassie comes to visit for a few days. She's so drop-dead gorgeous that Chandler can't stop staring; Ross makes a move on her; and Phoebe considers her options as well.
Rachel runs into a former college sorority sister (Melissa) with whom she made out once, while drunk. Melissa claims not to remember the event, until Rachel kisses her again (just to prove a point); then Melissa reveals she's been in love with Rachel ever since. Monica discovers Joey has invited his parents to the wedding, so she has to re-arrange the guest seating. Chandler and Ross get celebrity tuxedos through Rachel at Ralph Lauren, but Chandler doesn't want Ross's Batman tux to out-shine his 007 tux.
As Monica and Chandler prepare their wedding vows, they and their friends reminisce. The episode features numerous clips from previous episodes.
Chandler confronts his estranged cross-dressing father (KATHLEEN TURNER). Rachel gets into trouble driving Monica's Porsche.
In preparation for the wedding, Ross has the "big brother" talk with Chandler, telling him that if he ever hurts Monica, he'll kick Chandler's ass. This amuses everybody. Monica stresses that Rachel will forget one of her responsibilities. Joey gets a part in a World War I movie (Over There), with an actor (Richard) who teaches him that great acting means enunciation, and enunciation means you spit. The wedding rehearsal dinner is held; Chandler's parents feign civility. Chandler freaks out about becoming "the Bings" and disappears; Ross goes to look for him. The Geller parents stop by the coffee shop; Mrs. Geller takes a liking to Gunther. While Rachel and Phoebe wonder how to keep Monica from finding out Chandler is missing, Phoebe finds a positive pregnancy test in Monica's bathroom. Joey finds out he's scheduled to work the day of the wedding.
Rachel and Phoebe decide to keep their knowledge of Monica's pregnancy a secret. Joey tries to get out of filming, but can't. He only has one scene to do, but it drags on all day because the star is drunk. Ross and Phoebe find Chandler at his office and convince him to come back, one step at a time. Rachel stalls Monica, but is just about to reveal that Chandler is missing when Ross and Phoebe return with him. Joey still can't leave the set, so Rachel finds another minister, a Greek Orthodox Priest. Chandler is still a bit flighty, but then he overhears Phoebe mention Monica's pregnancy, and that brings him back to reality. Joey kidnaps the star so he can leave the set, and barely makes it to the ceremony in time. Chandler tells Monica he knows about the baby; but she tells him there is none. Unbeknown to everybody, Rachel is apparently the pregnant one.