At Rachel's birthday celebration, Chandler has accidentally revealed that Ross loves her. Rachel goes to the airport to meet Ross and tell him she cares for him, unaware he is returning with Julie (Lauren Tom), who he reconnected with in China and is now dating. Chandler then feels guilty for advising Ross to get over Rachel.

The guys are uncomfortable by seeing Carol breastfeeding Ben. The situation is made worse by Joey and Phoebe tasting the milk. Rachel resents Monica's growing friendship with Julie, though Monica feels obligated to spend time with her brother's girlfriend. At his department store job, Joey competes with a fellow cologne spritzer for a beautiful colleague's (Emily Procter) affection.

When Chandler refuses to date a woman from work, claiming her nostrils are too big, the gang claim this is always his way to avoid serious relationships. Rachel and Monica's downstairs neighbour, Mr. Heckles, suddenly dies, leaving them all his belongings, which is nothing but junk that they have to dispose of.

The gang is amazed that Phoebe has been secretly married to a gay Canadian ice dancer named Duncan (Steve Zahn). She married him so he could obtain a green card. Phoebe is excited when he wants to see her, then is crushed that he wants a divorce. Duncan says he realized he is not gay and wants to marry someone else.

When a sexy-sounding woman called Jade (Brittney Powell) calls the wrong number, Chandler seeks to exploit the situation, with ultimately embarrassing results. Income disparity issues divide the friends: the more affluent Ross, Chandler, and Monica versus the less-well-off Phoebe, Rachel, and Joey. Newly-promoted Monica is fired after accepting "gifts" from her restaurant's meat supplier, it being against restaurant policy regarding kickbacks.

When Monica rushes Ross to the emergency room after he suffers an allergic reaction to kiwis, Chandler and Joey babysit Ross' baby son, Ben. They use him as bait to attract girls, but women think they are a gay couple. After accidentally leaving Ben on a bus, they are unable to identify which of two babies is Ben at the city's lost & found.

Rachel goes on a date but after drinking too much wine, obsesses about Ross. Her date suggests she needs closure, so Rachel leaves a message on Ross' answering machine claiming she is "over" him. After hearing it the next morning, a stunned Ross wrestles with choosing her or Julie. Next, he visits a pet shop with Julie, where he shall choose between two cats Julie has shortlisted for him, a task that utterly overstrains him.

Ross struggles choosing between his childhood crush, Rachel, and his current girlfriend, Julie. Joey and Chandler suggest making a list of each girl's pros and cons. Ross chooses Rachel, ending it with Julie, though Rachel later finds the list, reading the negative comments. Hurt and angry, she breaks up with Ross.

On Christmas, Monica, strapped for cash looks for tips from people using home-baked cookies, receiving mixed reactions. Phoebe discovers that the framed picture of her father that her grandmother (Audra Lindley) keeps in her apartment is actually the photo model. She tries locating her real father, then decides she is unready to meet him.

Monica gets back together with Fun Bobby, who the other friends realize has a drinking problem. Monica persuades him to quit drinking, only to discover he is no longer fun. Joey lands the role of Dr. Drake Ramoray, a neurosurgeon on Days of Our Lives after refusing to sleep with the casting lady for a smaller role; she then offers him the bigger role of Ramoray, which he does sleep with her for.

Carol and Susan hire Monica to cater their lesbian wedding, though the upcoming nuptials soon runs into a snag that Ross helps untangle. Phoebe believes she is possessed by an eighty-two-year-old client's spirit who died during a massage session. The woman's widower tells Phoebe that his late wife did not want to die until she saw "everything.

Ross goes to visit Marcel while in California but the zoo says the monkey died. Ross soon learns Marcel is alive and working in commercials. Joey receives his first fan letter from a beautiful but crazed woman (Brooke Shields) who believes Days of Our Lives is real, a fact that does not prevent Joey from dating her.

Rachel and Monica compete for Jean-Claude Van Damme after meeting him on a movie set that Marcel is in. Chandler runs into Susie, a former schoolmate (Julia Roberts), working on the film. She seems attracted to him, but is actually seeking revenge for Chandler once humiliated her back in the fourth grade.

After getting his big break with Days of Our Lives, Joey pays Chandler back with $812 and gives him an engraved gold bracelet that Chandler thinks makes him look gay. Joey's feelings are hurt when he overhears Chandler complaining about it. 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 Rachel had a large nose.

Joey buys a big screen TV and two leather recliners with his soap opera salary, turning him and Chandler into "couch potatoes" who spend days watching TV and never getting out of the chairs. Monica has a catering job for handsome Dr. Richard Burke (Tom Selleck), an ophthalmologist, who is an old family friend.

Now that he has a steady income, Joey thinks he should have his own apartment and moves out, upsetting Chandler. Monica struggles to tell her parents that she is dating Richard. Rachel and Phoebe want to get tattoos. Phoebe chickens out at the last minute, resulting in nothing more than a tiny blue dot, while Rachel gets a heart tattoo embedded on her butt-cheek.

A record producer discovers Phoebe and wants to make a music video out of her song "Smelly Cat". The producer secretly dubs a more talented (but less attractive) woman's voice over Phoebe's, though Phoebe initially believes she is the one singing. Ross's new relationship with Rachel causes friction with Monica who resents her brother being around all the time.

Joey's good fortune comes crashing down when he foolishly claims in an interview for Soap Opera Digest that he writes all his own lines on Days of Our Lives, angering the script writer who then kills off Joey's character. Phoebe's attempt to help Chandler bond with his new roommate ends up revealing Eddie's quirky behaviour.

Creeped out by his bizarre new roommate, Eddie, Chandler demands he move out. Eddie agrees, then does not even remember the conversation. Obviously deranged, he imagines that he and Chandler took a trip to Las Vegas that never occurred. Joey struggles dealing with losing his job on Days of Our Lives and the accompanying downfall in his lifestyle.

Phoebe's positive outlook of the world is shattered when she learns how the movie, Old Yeller, really ends. She then starts watching all the films with melancholic endings that her mother used to forbid her from watching during her childhood and becomes seriously depressed, nitpicking over all the distressing details out of even the most cheerful films.

Ross and Chandler clash with two bullies at the coffee house over the couch where the gang usually hangs out, one of whom steals Chandler's hat. The bullies then eject Ross and Chandler from the coffee house for “hogging” the couch. Sick of drinking homemade “Kappucinos”, Ross and Chandler decide to stand up to the bullies.

Rachel comes back from her sister’s college graduation ceremony pissed at her parents for ruining it with their incessant rampage about the divorce. Concerned that her parents would not get along during her birthday party as well, she contemplates not inviting them to the party at all, though Monica has invited Rachel's mother, Sandra.

Phoebe catches chicken pox from Ross’s son just as her old flame, Ryan (Charlie Sheen), arrives in town on leave from the Navy. Even though he has never had chicken pox, he wants to be as close to her as possible and they end up spending the rest of the time being sick and trying not to scratch themselves.

Rachel agrees to be the maid-of-honor at her ex-fiancé's wedding, but a fashion faux pas draws much unwanted attention on her. This is made worse when she finds out that Barry has had slandered her for having syphilis and mental illness the day she runs out on their wedding in order to save his own ego.