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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. Joey has problems when his TV show is cancelled after just one airing.

Everybody begins planning for the wedding. Phoebe moves in with Ross. Napping in Rachel's bed because the duck threw up in his, Joey discovers that Rachel has been reading a trashy romance novel. Phoebe moves her massage parlor in Ross's apartment. Monica's parents spent her wedding money on a beach house, but Chandler has enough saved for a decent wedding.

Everybody toasts the engagement. Phoebe wants to be the musician at the wedding. Joey prepares for an audition where he must play a 19-year-old. After Chandler can't get it up for Monica, he worries about the consequences. Ross and Rachel debate a "bonus night". Monica catches them kissing and thinks Rachel is trying to steal her night.

Monica struggles to decide between Richard and Chandler. Meanwhile, Rachel and Phoebe discuss their backup plans if they are not married before the time they're 40.

Chandler plans to propose to Monica at dinner, but his plans go awry when Richard shows up. Phoebe and Joey join Rachel at a charity auction.

Chandler and Phoebe shop for a ring for Monica. Chandler finds the perfect one but Phoebe accidentally lets it get away. Rachel wants Paul to open up, but he opens up a bit too much. Ross and Joey think that Chandler's mad at them because he's preoccupied with the ring.

While visiting an art museum, Monica puts her name on a two-year waiting list to use the museum for a wedding. When Paul threatens to fire Ross if he doesn't stop seeing his daughter, Ross and Elizabeth take a trip up to her dad's mountain cabin. Unfortunately, Paul has the same idea and takes Rachel up to the cabin.

Ross asks his friends to keep him company when he meets Elizabeth's dad for the first time. Paul ends up hitting it off with Rachel. Phoebe decides to write "another" book, about Monica and Chandler. Joey may be fired from his sitcom when he has a fight with C.H.E.E.S.E.'s operator.

Joey gets an audition for the lead character in a new TV show. When the audition is rescheduled, Chandler takes the message but forgets to tell Joey. Then the group recalls some of Joey's less-than-spectacular acting moments.