Chandler and Monica want to kiss at midnight so they ask Joey for help. Joey tells Ross he's got to kiss Phoebe because he's the history with Rachel and obviously he can't kiss his sister. He tells Phoebe that Ross wants to kiss her and she says it's obvious. He then tells Rachel he's going to kiss her at midnight and she asks why. He tells her she can't kiss Ross because of all the history and then asks her whom would she rather be kissing: him or Chandler? They agree on him.
As 1999 approaches, the group all makes resolutions, most of which will require a lot of willpower to accomplish. Ross says he's only going to have one divorce this year and that he's going to make himself happy doing one thing new every day. Phoebe's resolution is to pilot a commercial jet. When Chandler makes fun of her she says his resolution should be to not make fun of his friends. Monica says Phoebe's got a better chance on her resolution than he's got of not making fun of them. Joey's resolution is to learn how to play a guitar since it's a skill he's got in his resume and he would love for it to be true. Phoebe offers to teach him. When Rachel starts gossiping about a couple that were at the party, Monica suggest her resolution should be to gossip less. She insists she doesn't gossip but the others disagree.Chandler's resolution is put to the test when Ross' date has a funny name. Phoebe starts giving Joey guitar lessons without a guitar. She tells him first she'll teach him the chords, only she doesn't know the names of the chords but she names them after the shape of her hands when she makes them. Chandler seats besides them and almost explodes out of the need to make fun of her.
Later Joey tells Phoebe he went to a guitar store and she freaks out when she finds out he touched a guitar. She tells him that if he wants to learn to play the guitar he can't touch one. After this, Ross arrives at the girls' apartment wearing a pair of leather pants. Chandler is dying to make fun of him and begs the others to make fun of him for him but everyone pretends they're great. Monica starts taking pictures and says that is her resolution and that it's the best one since everyone can enjoy it.
While Ross is at a date he starts to sweat and his leather pants start to stick. He goes to the bathroom and takes them off to get a little air but then finds out they shrink and he can't put them on again. Meanwhile Phoebe freaks out when she discovers that Joey has been learning the real names of the chords. Phoebe says he's questioning her methods and he says her method is stupid. Then, Rachel picks up the phone and hears a conversation between Monica and Chandler and finds out about them. They agree on faking doing laundry so they can meet later.At his date's bathroom, Ross calls Joey for help on his leather pants. Joey hesitates and tells him Chandler isn't home but Ross tells him that he can help. Joey tells him to use baby powder and when that doesn't work he tells him to use Vaseline. Ross freaks out when none of his ideas work and the mixture has made a weird paste on his thighs.
Rachel goes to Joey with the newly discovered news. She tells him he can't tell anyone but Joey backs off and tells her he doesn't want to know. He says he's tired of being the guy who knows all the secrets and has to keep them to himself. She asks what those secrets are and he tells her she's not supposed to be gossiping.
Ross' date tells him through the door that she's starting to freak out about him being locked in her bathroom. He comes out with his pant off and covered in the weird paste.Joey apologizes to Phoebe and asks her to be his teacher again and he promises not to touch a guitar until she knows he's ready. Then, she gives him the guitar and he almost breaks it even before playing a chord.
Later, Ross gets to the girls' apartment with his pants in his hands. He complains about the fact that this year was supposed to be great and that in its second day he's already a loser. The guys pretend to disagree but he tells them to take a look at him. They try to comfort him with a picture Ben drew of him as a cowboy and he starts to think he should get another pair of pants. All of this happens with Chandler dying to make fun of him. Right after that Monica says she's going to do the laundry and Chandler says he'll go with her. Rachel watches them in pain since she can't say anything to anyone because of her resolution. Phoebe says she'll go to the airport to see if someone leaves a plane unattended so she can fly it. Rachel then tells Joey that if he found out on his own about her secret then they could talk about it and he agrees. So she tells him to go get her a book from Chandler's bedroom and they start to ask each other if they know anything. They both agree for a moment that neither can tell the other about it. Rachel threatens to go to Chandler's bedroom and finding out the things she thinks she knows. It's only then that Joey is certain that she know about Chandler and Monica. She asks him how long has he known and he says he's known for too long. He reminds her that she can't say anything to anybody because Chandler and Monica are too weird about that. Right then Phoebe enters the apartment and says since it's raining and she doesn't like to fly in the rain she decided not to go the airport. Joey and Rachel say they're going for a walk in the rain just so they can keep talking about Chandler and Monica. Phoebe thinks they're acting weird and then thinks they're having sex.
At the end, Chandler walks in on Monica and Ross at Central Perk and says he can't take it anymore and pays Ross the 50 bucks he bet on his resolution. Then he starts making all the jokes he couldn't make when all the stuff that happened were hilarious.