After the wedding ceremony, Emily locks herself in the bathroom. When Rachel points out that at her wedding to Barry, she escaped through the bathroom window, they burst into the bathroom to see that Emily has done the same thing. Monica and Chandler spend the entire reception trying to find a place to sleep together, but Rachel's desire to tell Ross about her feelings, Ross's search for Emily, and Emily's drunken father prevent them from doing so.
Ross hopes Emily will turn up at the airport the next day to join him for their honeymoon to Greece. He runs into Rachel during the last boarding call and invites her along since it seems Emily won't be arriving. However, Emily does show up, just as Ross is boarding the plane with Rachel. She runs off, and Ross chases her, leaving Rachel alone on the flight. Once Rachel returns from Greece, she finally tells Ross of her continued feelings for him. They both find it crazy when they realize that Rachel is in love with a married man whose wife won't return his calls.
Ross continues calling everyone in Emily's family to try to find her and sends them packages of flowers and giant stuffed animals. Annoyed by Ross's repeated, failed attempts to win her over, Emily finally contacts Ross to tell him to stop harassing her and her family. She eventually agrees to giving their marriage a chance, making a few demands in the process: Ross must move into a new apartment, because everything that is in his old apartment reminds her of Rachel; additionally, Ross must cut Rachel out of his life. While Ross agrees to move out of his apartment, he eventually draws the line at cutting Rachel out of his life. Emily's inability to trust Ross results in her deciding to end their marriage. Sometime later, Emily leaves a message on Ross's answering machine and wonders if the divorce was a mistake - even though she is set to marry another man. Rachel accidentally deletes the message, but still tells Ross about it. Ross refuses to call Emily back, not wanting to reunite with his manipulative and controlling ex-wife.
Rachel begins dating a man who lives in the apartment building, Danny, but stops seeing him after she realizes he has an inappropriate sexual relationship with his sister. Ross is forced to take a hiatus at work after screaming at his boss for eating his "moistmaker" sandwich. Eventually, he moves into Ugly Naked Guy's apartment across the street from Monica's.
After sleeping with each other while in London, Monica and Chandler decide to establish a secret relationship. Joey is the first to find out about Monica and Chandler's relationship early in the season after they take a secret vacation together. Rachel finds out mid-season, when she ends up eavesdropping on a phone call, and Phoebe is the last person to find out about the relationship when she sees them through the window of Ross's new apartment. Joey, Rachel and Phoebe confront Monica and Chandler about their deception by playing a trick on them, and Chandler and Monica finally admit that they have fallen in love with each other. Ross also finds out about Monica and Chandler's relationship after seeing them through the window of his new apartment. After realizing that Monica and Chandler are actually in love, he is happy for them.
Joey receives a role in a movie filming in Las Vegas. Chandler is going to drive to Nevada with him, but before they leave New York, Chandler accidentally reveals that he doesn't think the movie is Joey's big break and Joey kicks him out of the car. When he arrives in Las Vegas, he finds out the movie has run out of funding and been put on hold indefinitely. He gets a job as a gladiator character at a hotel and casino. The rest of the friends discover this when they plan a trip to Las Vegas to visit. During this trip, Chandler and Monica begin to wonder if they are seeing signs that are telling them that they should get married. However, when they get to the chapel, Ross and Rachel run out, having just drunkenly gotten married.
It received Emmy nominations in 1999 for Outstanding Comedy Series.
- The first lines of the season are "Friends, family..." spoken by the minister at Ross and Emily's wedding.
- In all of her appearances in Season 5 Helen Baxendale was pregnant.
|1||98||"The One After Ross Says Rachel"||Seth Kurland||Kevin S. Bright||September 24, 1998|
|Ross's nuptials continue after his slip-of-the-tongue but wedded bliss doesn't follow. Monica and Chandler try continuing their affair but can't steal a moment alone.|
|2||99||"The One With All The Kissing"||Wil Calhoun||Gary Halvorson||October 1, 1998|
|Ross's attempts at reconciling with Emily go unheeded. Chandler and Monica's affair is challenged by their "Not-in-New York" rule.|
|3||100||"The One Hundredth"||Marta Kauffman & David Crane||Kevin S. Bright||October 8, 1998|
|Phoebe is rushed to the hospital, where triplets are born. Joey gets hospitalized next - when his sympathy labor pains turn out to be kidney stones. An unsuspecting Rachel arranges a date for Monica with a male nurse.|
|4||101||"The One Where Phoebe Hates PBS"||Michael Curtis||Shelley Jensen||October 15, 1998|
|Phoebe resents Joey's PBS telethon gig because of a long-running grudge she holds against the network. To cover up her affair with Chandler, Monica tells Rachel she's dating someone from work.|
|5||102||"The One With The Kips"||Scott Silveri||Dana De Vally Piazza||October 29, 1998|
|Monica and Chandler go to Atlantic City for a weekend by themselves. Ross tries to tell Rachel they can't be friends once Emily arrives in New York.|
|6||103||"The One With The Yeti"||Alexa Junge||Gary Halvorson||November 5, 1998|
|While rummaging in the storage room, Monica and Rachel meet a hairy neighbor they first mistake for a yeti. To smooth things over with Emily, Ross agrees to de-Rachelize his apartment.|
|7||104||"The One Where Ross Moves In"||Perry Rein & Gigi McCreery||Gary Halvorson||November 12, 1998|
|With his marriage on the rocks, Ross moves in with Chandler and Joey. Rachel is convinced that her neighbor Danny is trying to seduce her with mind games.|
|8||105||"The One With All The Thanksgivings"||Gregory S. Malins||Kevin S. Bright||November 19, 1998|
|The gang reminisces about their worst Thanksgivings. Phoebe's takes her back to 1862. Elaborate tales are spun to try and uncover Monica's worst memory.|
|9||106||"The One With Ross' Sandwich"||Andrew Reich & Ted Cohen||Gary Halvorson||December 10, 1998|
|Ross is enraged when someone at work steals his Thanksgiving leftovers sandwich. Joey threatens to crack under the strain of knowing about Monica and Chandler's affair.|
|10||107||"The One With The Inappropriate Sister"||Shana Goldberg-Meehan||Dana De Vally Piazza||December 17, 1998|
|Monica maneuvers Rachel and Danny into dating but Rachel has second thoughts after observing Danny's unusually close relationship with his sister.|
|11||108||"The One With All The Resolutions"||Teleplay by Suzie Villandry, Story by Brian Boyle||Joe Regalbuto||January 7, 1999|
|As the new year approaches, everyone makes resolutions, some more realistic than others. Ross's resolution causes him to wear hot leather pants on a date...perhaps too hot.|
|12||109||"The One With Chandler's Work Laugh"||Alicia Sky Varinaitis||Kevin S. Bright||January 21, 1999|
|Monica uncovers the fake laugh Chandler reserves for his boss's bad jokes. Rachel is upset that Monica hasn't 'fessed up about her affair. Word comes of Emily's remarriage plans.|
|13||110||"The One With Joey's Bag"||Teleplay by Seth Kurland, Story by Michael Curtis||Gail Mancuso||February 4, 1999|
|When Rachel helps Joey change his image to help him land an acting gig, she includes a shoulder bag that's rather purselike. Phoebe is shocked when her dad attends her grandmother's funeral.|
|14||111||"The One Where Everybody Finds Out"||Alexa Junge||Michael Lembeck||February 11, 1999|
|When Phoebe finds out about the Monica/Chandler affair, she tests Chandler via flirtation. Ugly Naked Guy's apartment goes up for rent and Ross wants it.|
|15||112||"The One With The Girl Who Hits Joey"||Adam Chase||Kevin S. Bright||February 18, 1999|
|When Joey starts dating Katie, he finds she packs a painful punch. Ross has trouble making friends with his new neighbors.|
|16||113||"The One With The Cop"||Teleplay by Gigi McCreery & Perry Rein, Story by Alicia Sky Varinaitis||Andrew Tsao||February 25, 1999|
|Phoebe finds a police badge inside the Central Perk sofa. Rather than return it, she decides to embark on a "good-deeds" campaign. Joey is unnerved by his romantic dream about Monica.|
|17||114||"The One With Rachel's Inadvertent Kiss"||Andrew Reich & Ted Cohen||Shelley Jensen||March 18, 1999|
|After a job interview, Rachel impulsively kisses her potential boss on the cheek. Phoebe and Gary vie for "steamiest-affair" with Monica and Chandler.|
|18||115||"The One Where Rachel Smokes"||Michael Curtis||Todd Holland||April 8, 1999|
|Rachel takes up smoking at her new job as a way of making inroads with the boss. Ross's son Ben joins Joey on an audition for a soup commerical.|
|19||116||"The One Where Ross Can't Flirt"||Doty Abrams||Gail Mancuso||April 22, 1999|
|Joey's Italian-speaking grandma joins the gang in watching his Law & Order debut. Ross decides to order lots and lots of pizza in order to flirt with the delivery girl.|
|20||117||"The One With The Ride-Along"||Shana Goldberg-Meehan & Seth Kurland||Gary Halvorson||April 29, 1999|
|As Emily's wedding nears, the group does its best to distract Ross. A gunshot and a meatball sandwich take center stage when the guys go out on the beat with Phoebe's cop boyfriend.|
|21||118||"The One With The Ball"||Teleplay by Greg Malins, Story by Scott Silveri||Gary Halvorson||May 6, 1999|
|Phoebe asks Chandler to talk Gary out of asking her to move in with him. To fulfill a childhood dream, Rachel buys a sphinx cat which doesn't behave as planned.|
|22||119||"The One With Joey's Big Break"||Teleplay by Wil Calhoun, Story by Shana Goldberg-Meehan||Gary Halvorson||May 13, 1999|
|Joey is excited about landing a lead role in a movie shooting just outside Las Vegas - but furious with Chandler after he confesses his doubts that it will be his "big break".|
|23||120||"The One In Vegas, Part 1"||Andrew Reich & Ted Cohen||Kevin S. Bright||May 20, 1999|
|After his film gig falls through, Joey begs Chandler not to visit. But when Monica decides to celebrate her one-year anniversary with Chandler in Vegas, no one wants to be left behind.|
|24||121||"The One In Vegas, Part 2"||Greg Malins & Scott Silveri||Kevin S. Bright||May 20, 1999|
|Joey tries to convince a blackjack dealter with identical hands to join him in a business venture. While playing craps with Monica, Chandler makes the bet of a lifetime.|