Rachel goes to pick up Ross from the airport, only to find that he got a new girlfriend. Monica is impressed by Joey and Chandler’s new haircuts, and asks Phoebe to give her one. Chandler has a terrible incident when he goes to see Joey’s tailor.
Joey and Chandler freak out when they see Carol breastfeeding Ben. As Monica tries to be nicer to Julie for Ross’s sake, Rachel feels she’s betrayed her. Meanwhile, Joey has trouble at work, after the arrival of a new guy.
When the downstairs neighbor, Mr. Heckles, dies, the girls are surprised to learn that he’s left them all his possessions; meanwhile, Chandler is shocked by the similarities between him and Heckles, and worries about ending up alone like him.
As Phoebe’s gay ice dancer friend stops by, they all learn that Phoebe married him to help him get a green card, but when they confront her, it leads to other secrets being revealed. Meanwhile, Ross asks for Rachel’s advice on taking his relationship with Julie to the next level.
With Ross’s birthday approaching, a problem spoils the gang’s plans, as the issue of money causes a rift among the six of them, all the while, Chandler tricks a woman, who called him by mistake, to score a date with her.
When Ross suffers an allergic reaction to Monica’s pie, she takes him to the hospital, so Joey and Chandler end up babysitting Ben. Meanwhile, Phoebe protests as the coffee house manager gets a professional singer to replace her.
When Monica fixes Rachel up with a date, she ends up getting drunk and leaving a message on Ross’s answering machine where she confesses her feelings for him. After losing her job, the relentless Monica embarks on a new project, which is to help Chandler lose weight.
With Ross being torn between Rachel and Julie, Chandler suggests making a pros and cons list to help him decide, but it ends up causing trouble. A desperate Monica gets a job coming up with recipes for Mockolate, a revolting substitute for chocolate.
As Phoebe finds out that her grandmother has been lying to her about her father’s identity, she starts looking for her real father. Meanwhile, the cash-strapped Monica hands out cookies as Christmas tips, and Rachel gives Ross a taste of his own medicine.
As Monica and Fun Bobby get back together, the gang learns he’s called ‘Fun’ Bobby for a reason. Joey gets a lucky break, as he’s picked to play a part in a soap opera. When Rachel announces that she has a date, the gang is stupefied upon meeting her date.
Rachel’s mother drops in with shocking news. With Carol and Susan’s wedding in the offing, they hire Monica to be their caterer. When a client of Phoebe’s dies, she believes that the woman’s spirit went into her body, so she tries to help the woman finish her unfinished business on earth.
While in California, Ross tries to visit Marcel, but he’s surprised to learn what has become of him. A beautiful, yet nutty fan starts stalking Joey. As Phoebe gets a gig singing for children at the library, her attempts to write special songs for them receive mixed reactions.
When Ross takes the gang to visit Marcel on the set of the film he works in, the girls meet Van Damme, whom Monica has a crush on, but Rachel ends up going out with him, which causes a rift between the two. Chandler meets a former schoolmate, who asks him out with an ulterior motive.
With Joey finding success and earning money, he gets Chandler a gift, which he turns out to hate. The gang gathers to watch a video of Monica and Rachel’s prom night.
As Joey and Chandler get new recliners and a big TV, they get so lazy and use others to cater to them. Meanwhile, Monica falls for an old family friend, and Ross and Rachel’s first date is almost ruined, but they manage to turn it around.
After having a fight with Chandler, Joey decides to get his own place, especially since he can afford it now. Monica goes with Ross and Richard to her father’s birthday party, where she tries to keep her relationship with Richard secret. Rachel and Phoebe decide to get tattoos.
Ross starts getting on Monica’s nerves now that he’s dating Rachel and spending more time at their apartment. Phoebe’s song “Smelly cat” gets made into a music video. With Chandler missing Joey, he gets a new roommate called Eddie.
As Chandler tries to connect with Eddie, he’s taken aback by his freakish behavior. Owing to a slip of the tongue, Joey’s character in the soap opera is killed off. When Monica and Richard discuss their former lovers, the issue causes Ross and Rachel to have a spat.
Chandler desperately tries to have the unstable Eddie move out. Meanwhile, Joey is forced to deal with the ramifications of losing his high-paying job. A book about women’s empowerment causes the girls to fall out.
As Chandler and Joey bond with Richard, Monica starts feeling jealous. Phoebe’s world turns upside down when she accidentally watches the end of a sad movie that she thought was a happy one. Rachel freaks out when she discovers that Ross has their whole future mapped out.
Ross and Chandler get bullied by two guys at the coffee house. A desperate Monica turns to the stock market so as not to accept a lousy job at a diner. Phoebe finally decides to meet her real father.
On her birthday, Rachel ends up having two parties in two different apartments, as both her parents, who are going through a divorce, show up, forcing the gang to go out of their way to ensure that they don’t see each other.
As Phoebe announces that an old lover of hers is coming to town, she gets chickenpox. When Chandler gets Joey a job at his office, he ends up regretting it. Monica complains that Richard doesn’t have any idiosyncrasies.
As Rachel goes to Barry and Mindy’s wedding as the maid of honor, a few mishaps occur, but she manages to overcome them. Joey tries to practice kissing guys for an upcoming audition. Monica finds out that she and Richard want different things.