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School time friends begin to live together in two flats in New York City, but their emotions from the past begin to affect their present love and career choices.
The One with Ross’s New Girlfriend
Rachel decides to tell Ross that she loves him and waits for him at the airport, not knowing he is returning with a new girlfriend named Julie (Lauren Tom) thanks to Chandler’s advice. Chandler feels guilty because he told Rachel that Ross loves her after he had advised Ross to get over his feelings for her. Joey and Chandler get their hair cut by Phoebe, and Monica wants her hair cut too, but Phoebe gives her an awful haircut. Chandler needs a suit, so Joey takes him to his tailor, who touches Chandler inappropriately. Chandler tells Joey of this, but Joey insists that is how pants are measured. Ross annoys everyone by talking about Julie, and Rachel becomes so desperate and upset that she spends the night with her old lover, Paolo, the Italian "stud" from Season 1.
The One with the Breast Milk
The guys are uncomfortable with Carol breastfeeding Ben, and the situation is made worse by Joey and Phoebe tasting it. Rachel is uncomfortable with Monica’s growing friendship with Julie. At his day job, Joey competes with a fellow cologne spritzer for the affection of a beautiful colleague (Emily Procter).
The One Where Heckles Dies
Chandler refuses a date with a woman from work, claiming that it is because her nostrils are too big, but truthfully he is trying to escape a potentially serious relationship. When Rachel and Monica’s downstairs neighbour Mr. Heckles dies and leaves all his belongings to Monica and Rachel, Chandler discovers eerie similarities between his life and the life of Heckles. Not wanting to end up alone like Heckles did, he calls Janice in hopes to rekindle their relationship, only to learn that she is married with a baby on the way. Ross and Phoebe have a dispute over the progression of evolution when Phoebe says it’s "Too Easy".
The One with Phoebe’s Husband
The gang is amazed to learn that Phoebe married a gay Canadian ice dancer Duncan (Steve Zahn) to help him get his green card. Phoebe thinks that she still cares for him, but then he shows up asking for a divorce as he lied to himself about being gay and wants to marry someone else. Interesting facts are revealed about the others, too: Joey starred in a porn film and Chandler has a third nipple. Ross seeks relationship advice from Rachel after revealing that he and Julie have yet to consummate their relationship. Rachel, because she still loves Ross, gives him bad advice, hoping that he and Julie will break up as a result. Unfortunately for Rachel, Joey also gives Ross advice.
The One with Five Steaks and an Eggplant
When a sexy woman calls the wrong number, Chandler seeks to make the most of the situation. Income issues divide the friends: the well-off Ross, Chandler and Monica versus the not-so-well-off Phoebe, Rachel and Joey. Monica loses her job after accepting "gifts" from her restaurant’s meat supplier.
The One with the Baby on the Bus
When Ross has an allergic reaction to Monica’s kiwi-lime pie, Chandler and Joey are asked to baby-sit Ross’s son, Ben. While using Ben to help them try to pick up girls, they accidentally leave him on a bus. Although they later locate him, they are not sure the baby is really Ben. Phoebe loses her Central Perk singing gig to a professional singer (Chrissie Hynde), and she becomes a street singer in front of the café. Lea Thompson from Caroline in the City makes an appearance, not as her character Caroline but as a woman with a gay brother interested in where Joey and Chandler adopted Ben. Also, Giovanni Ribisi, who in later episodes portrays Frank Buffay Jr., appears in this episode as a stranger who dropped a condom in Phoebe’s guitar case and comes back to get it for "an emergency." The personality of this character is rather similar to Frank Jr’s; though not confirmed, they are possibly the same person. Catherine Bell also appears as Robin, one of the girls in the bus.
The One Where Ross Finds Out
A drunken Rachel is persuaded to call Ross and reveals her feelings for him on his answering machine. When he finds out, he must make the choice between her and Julie. Meanwhile, Monica finds work as Chandler’s personal trainer and Phoebe has a hard time trying to get her boyfriend to have sex with her. She seeks Joey’s advice. Ross and Rachel argue, and Ross says that he is not leaving Julie. At the end of the episode Ross and Rachel kiss.
The One with the List
Ross is still compelled to make a choice between his childhood crush Rachel and his current lover Julie, and enlists Joey and Chandler’s help in making a list of the pros and cons of each. He chooses Rachel, but she finds the list and gets angry with Ross. Meanwhile, Monica gets a job making food with a disgusting synthetic chocolate substitute called Mockolate.
The One with Phoebe’s Dad
It’s Christmas time and Monica tries tipping with cookies, rather than cash, with mixed results. Phoebe learns that the guy in the pictures her grandmother keeps around is not her father but the Macy’s photo frame model. She tries to track down her real father, but in the end she feels that she is not ready to meet him. Chandler and Joey wait too late to shop for presents, and are forced to buy gifts from a gas station. Ross asks Rachel to make a list about him, but he is offended when she calls him obsessive.
The One with Russ
Monica gets back together with Fun Bobby, who has a drinking problem. She successfully helps him give up drinking, but then he is unhappy and not fun anymore. Joey gets chosen to play the role of Dr. Drake Ramoray, a neurosurgeon on Days of Our Lives after he sleeps with the casting lady. Rachel begins dating a guy named Russ, who bears an uncanny resemblance to Ross (both roles were played by David Schwimmer, yet Russ is credited as being played by "Snaro", a pseudonym of Schwimmer’s and a tribute to a friend). Eventually, Rachel dumps Russ, telling him he reminds her of someone, though she doesn’t tell him about his resemblance to Ross. In the end Russ and Julie (Lauren Tom) hook up.
The One with the Lesbian Wedding
Carol and Susan get married, providing Monica with a job: catering the wedding. Phoebe is possessed by the spirit of an eighty-two-year-old massage client who dies in the middle of a session. Rachel’s mother (Marlo Thomas) comes to visit and announces that she has decided to divorce her husband, Rachel’s father.
The One After the Superbowl, part 1
Ross goes to visit Marcel while on a trip to California, and finds that the monkey is working in commercials. Joey gets his first fan letter and ends up dating the woman (Brooke Shields) who sent it. She turns out to be a mentally ill stalker who thinks that the happenings on Days of Our Lives are real. Phoebe is asked by a man (Chris Isaak) to sing for the children at a library, but their parents are horrified by her morbid lyrics. However, the kids like the songs and come to the café to listen to her.
The One After the Superbowl, part 2
Rachel and Monica compete for the affections of Jean-Claude Van Damme after meeting him on a movie set. Chandler meets a former schoolmate (Julia Roberts), a makeup artist, who seems to be attracted to him but it turns out that Chandler once embarrassed her and she just wants to get revenge. An excited Joey gets a role as an extra in the movie, and Ross and Marcel go on a whirlwind tour of the city.
The One with the Prom Video
After getting his big break with Days of Our Lives, Joey pays Chandler back with $812 and an extremely tacky engraved gold bracelet. Also, an unemployed Monica is hard up for money. A home video from Monica and Rachel’s prom night reveals that Monica was previously overweight, and that Rachel had a large nose. Rachel seemed to have been stood up by her prom date, so Ross puts on his father’s tuxedo to take her to prom himself, but Rachel’s date shows up and they leave before she learns of Ross’s plans. The video then shows a speechless and devastated Ross standing at the top of the stairs. The candor of Ross’s heartbreak compels Rachel to kiss Ross.
The One Where Ross and Rachel...You Know
Joey buys a big screen TV and two leather recliners with his newfound money, resulting in him and Chandler spending two days watching TV and never getting out of the chairs. Monica has a catering job for an ophthalmologist and a friend of her parents, the attractive Dr. Richard Burke (Tom Selleck), and later they go on a date. Ross and Rachel attempt to have their first real date, but it’s difficult for Rachel to overcome their long friendship. As they tried to schedule another date, Ross has an emergency at the museum and ends up having sex with Rachel for the first time.
The One Where Joey Moves Out
Joey thinks he needs to move out of Chandler’s apartment and wants to get a new one to ’give him time to think’. Monica struggles to tell her parents about her relationship with Richard. Rachel and Phoebe want to get a tattoo. Phoebe chickens out and Rachel gets a heart.
The One Where Eddie Moves In
Phoebe is discovered by a record producer who wants to make her song "Smelly Cat" a video, but who secretly dubs in the voice of a more talented (but less attractive) woman. Ross’s new relationship with Rachel makes Monica feel like she’s living with her brother again... and she hates it. And Joey considers moving back in with Chandler, but Chandler already has a new roommate, Eddie.
The One Where Dr. Ramoray Dies
Joey finds out the hard way that it’s not wise to boast falsely; his soap opera character is scripted to fall down an elevator shaft and die after Joey brags of writing his own lines in an interview. Phoebe helps Chandler bond with his new roommate...to Chandler’s horror. And sexual history dominates the discussion between two couples—Monica and Richard, and Ross and Rachel.
The One Where Eddie Won’t Go
Creeped out by his bizarre new roommate, Eddie, Chandler demands that he move out. Eddie agrees, but doesn’t move out — nor does he even remember the conversation, as he is obviously mentally ill, imagining he and Chandler took a trip to Las Vegas and believing it to have really happened. Joey has trouble coming to grips with the death of Dr. Ramoray and the accompanying change in his lifestyle. And a new book on empowerment for women inspires the female friends to have a "goddess meeting." Joey moves back in with Chandler, they kick out Eddie and they make up with each other.
The One Where Old Yeller Dies
Phoebe’s world view is shattered when she learns how Old Yeller really ends. She watches all the films her mother didn’t let her watch and becomes depressed. Monica becomes jealous when Richard begins hanging out with other people: namely, Joey and Chandler. However, this is short lived as Joey and Chandler confess to thinking of Richard as a fatherly figure, when Richard was under the impression that they were just buddies. Rachel becomes stressed out when she learns that Ross has planned their whole life together.
The One with the Bullies
Chandler and Ross run into two bullies at the coffee shop, one of whom steals Chandler’s hat. Monica, down to her last few dollars of savings, plays the stock market based solely on the ticker symbols to avoid taking a job at a tacky 1950s themed diner. Phoebe makes multiple attempts to visit her birth father, but instead she meets her half-brother, Frank Buffay Jr., and learns that her father hasn’t been home for four years. Monica eventually loses her savings due to her unwise investments, and is forced to work at the Moondance Diner, dressed in a ridiculous costume and dancing on the counter to songs by The Village People.
The One with the Two Parties
The gang plans a surprise party for Rachel, but the real surprise is when both of her estranged parents show up for the same party.
The One with the Chicken Pox
Phoebe catches chicken pox just as her old flame Ryan (Charlie Sheen) arrives in town on leave from the Navy. Even though he hasn’t yet had chicken pox, he can’t stand to be apart and they both spend the rest of the time sick and trying to not scratch at the sores. Joey gets a job at Chandler’s office but decides to play it as a role. The character he creates, Joseph, has a wife and kids and ultimately blames Chandler for his own screw ups. Monica is upset that Richard doesn’t have a "thing": an unexplainable quirk. He eventually comes up with one to ease her mind.
The One with Barry and Mindy’s Wedding
Rachel agrees to be maid of honor at her ex-fiancé’s wedding, but a fashion faux pas focuses attention away from the bride. To get a role in Warren Beatty’s new movie, Joey needs to practice kissing guys. Monica ponders her future with Richard and Chandler falls for a mystery woman on the Internet who turns out to be his ex-girlfriend, Janice. Richard doesn’t want to have children, but Monica does, so she breaks up with him.