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.

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.

Phoebe's grandmother dies, and Phoebe is shocked when her father turns up at the funeral. Meanwhile, Rachel gives Joey a "man's bag" for an audition, and Chandler is scared to tell Monica he doesn't like her massages.

When the friends discover that Ugly Naked Guy is moving out of his apartment, Ross leaps at the opportunity to get his own place again. Phoebe finds out about Monica and Chandler's relationship, and tries to get them to reveal the truth by seducing Chandler.

Joey starts dating Katie, a little girl who packs a mean punch. When Ross refuses to contribute to the retirement fund of the building's maintenance man, he winds up offending everyone in the building. Meanwhile, Chandler freaks out about his relationship with Monica.

Joey has a dream about Monica and becomes convinced he is in love with her. Meanwhile, Phoebe finds a police badge in Central Perk and uses it to go on missions of mercy. And Ross buys a new sofa but has trouble moving it up the stairs into his new apartment.

Monica becomes jealous of Phoebe and Gary. Rachel has an awkward encounter when she interviews for a new job. Joey tries to meet a girl living in Ross's building, but has trouble with finding her apartment.

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.

As Joey's Italian-speaking grandmother visits to watch him on TV, Ross has trouble flirting with the pizza delivery girl, and Rachel tries to find an earring of Monica's that she has misplaced.

While the guys go on a ride-along with Gary, Rachel accidentally deletes a message from Emily on Ross's answering machine.