Chandler decides the only way to mend his friendship with Joey is to fly out to Vegas and visit him. Phoebe is determined not to be left out on another adventure, so everyone winds up going. Trouble is in the water, however, when Chandler finds out that Monica had lunch with Richard. Meanwhile, Ross and Rachel try to embarrass each other after an awkward encounter. Chandler and Monica reconcile and hastily decide to get married. Ross and Rachel get drunk and roam the casino. Phoebe deals with a 'lurker' on the slot machines.
Joey seems to have finally hit big when he gets offered a lead part in a movie shooting outside of Las Vegas. However, when Chandler begins expressing doubts about the film's legitimacy, it causes a rift in their friendship. Also, Rachel gets an eye infection but is reluctant to seek treatment because of her eye phobia. And Phoebe is mad at Ross, but doesn't know why.
Phoebe learns that Gary is going to ask her to move in with him and thinking this is way to fast, she tries to get Chandler to talk him out of this decision. Rachel buys an expensive sphynx cat but is disappointed when it doesn't behave as she hoped it would. Meanwhile, Ross and Joey start throwing a ball while they are bored but it changes from a time-filler to a super-competitive obsession when Monica joins in.
Rachel decides to start smoking in order to avoid missing important meetings with her boss. Meanwhile, Ben gets offered an audition for a soup commercial, and Joey auditions to be Ben's father during the ad. Also, Monica and Phoebe plan a surprise birthday party for Rachel together, but Monica takes over.
Monica begins to hang out with Chandler during his work functions, since they don't have to keep their relationship a secret among his coworkers. However, she learns that Chandler has a second, more annoying personality when he's around his boss. Meanwhile, Ross learns that Emily is getting remarried and in his grief hooks up with an old nemesis of the gang: Janice.
With the New Year, the friends make New Year's resolutions. Ross resolves to try a new thing every day. Chandler resolves to not make fun of his friends for a week. Joey resolves to learn how to play the guitar, with Phoebe as his teacher. Rachel resolves to give up gossiping. Chandler nearly goes insane holding it all in. Ross is stuck in a sticky situation at his date's apartment, in constricting and hot leather pants. Rachel discovers a big secret (Monica and Chandler) that threatens to spoil her resolution.
Joey teaches Ross how to be unemployed. Phoebe is working for the Salvation Army during the holidays. Monica is tired of Rachel's obsessing about Danny and asks him to go out with her. Ross convinces Joey to write a play about himself. Phoebe is distressed after finding out that New Yorkers are mean. Rachel meets Danny's sister and is dismayed when the two seem a little too playful. Phoebe vows a return to "Street Phoebe."