Rachel thinks she's engaged to Joey, but isn't sure she feels right about it. Rachel tells Phoebe about it, but Phoebe thinks Rachel is talking about Ross. Phoebe congratulates Ross and Ross is confused. Joey tries to fix the situation, but is too late. Joey, Ross and Rachel finally work things out all together, and then Joey leaves Ross and Rachel alone together with a nursing baby Emma. Ross and Rachel talk about trying to have a relationship again, but then Ross realizes that Rachel accepted Joey's mistaken proposal. Monica's father busts her and Chandler trying to make a baby in a closet in the hospital and tries to help them.

When Rachel and Phoebe go out for a girls' night out, Rachel ends up giving her phone number to a charming guy in a bar and then panics when she realizes that Ross could pick up the phone when the guy calls later that night. Meanwhile, Ross has invited Mike to hang out while the girls are out on the town, and the two men spend a torturous evening realizing they have absolutely nothing to talk about. Phoebe calls Mike and begs him to intercept all incoming phone calls, which he does, but the only thing he accomplishes is freaking out Ross. Ross ends up getting the phone call, but doesn't give Rachel the message. Chandler sneaks into New York to see Monica without telling Joey, but when Joey sees Monica in a slinky dress with two glasses of wine, he thinks Monica is having an affair. Chandler tries a complicated maneuver to clear Monica in Joey's eyes, but Joey ends up busting the guilty couple.

Phoebe and Joey purposely set up Ross and Rachel on lousy blind dates so that they'll realize they should actually be together and be a family with Emma. Ross gets stood up, and becomes the subject of a bet by restaurant waiters, while Rachel ends up with a loser of a guy who constantly talks about what a loser he is. Joey is horrified when he finds Chandler and Monica having sex when they're supposed to be babysitting Emma, and threatens to tell Rachel about it if they don't name their firstborn child Joey.

Joey gets a part in a Broadway play by impressing the famous director with his I-have-to-pee performance. After Phoebe and Ross are mugged by one of Phoebe's old friends from her living-on-the-street days, it comes to light that Phoebe mugged Ross when she was 14 years old. Chandler gets a job as an intern at an advertising agency. He feels like he can't possibly compete with the college students that share his lowly position, but he manages to impress his boss with ideas that come from life experience.

Chandler and Monica, low on funds, each secretly go to Joey to borrow money. When Chandler realizes that Monica borrowed money from Joey before he did, Joey lies to Chandler and says that Monica borrowed the money for a boob job. Chandler freaks out and, without revealing what Joey told him, tries to communicate to Monica that he likes her body just the way it is, but Monica misunderstands and thinks Chandler is worried about how her body will change when she gets pregnant. Mike and Phoebe decide to move in together, but when Phoebe finds out that Mike never wants to get married ever again after his first disastrous marriage, she realizes that she does want to get married someday, and so they break up instead. Rachel babyproofs her and Joey's apartment, and Joey finds that he can't get into anything anymore.

Chandler and Ross start posting silly things about each other on their college alumni web site, until Chandler takes it a step too far and posts that Ross has died. Ross is angry with Chandler until he realizes that no one has posted or called with condolences. Ross becomes obsessed with finding out if anyone would mourn him if he really died, and forces Chandler to host a fake memorial service for him. One beautiful woman shows up and admits that she used to have a crush on Ross, but when Ross reveals himself to be alive, she calls him a sick man and runs away. Joey goes to battle with Emma over an old favorite stuffed animal. Monica tries to help Phoebe stay away from Mike after their break-up, but when she hears Mike profess his feelings for Phoebe, even Monica can't help but encourage Phoebe to sleep with him one last time.

The friends decide to pool their money and buy a big block of tickets for the multimillion-dollar powerball jackpot. Ross originally scoffs at the others for their lottery fever, but ends up getting caught up in it. Before they even know if they've won, the friends start to fight over the tickets, and when Phoebe tries to stop the fighting she loses half the tickets due to a stray pigeon the balcony. The friends don't win anything, but they find out later that a guy who found a ticket on the street won $10,000. Rachel and Ross eagerly await Emma's first word, which turns out to be "gleba," an esoteric scientific term. Chandler is depressed when three of his fellow interns get offered the three open assistant jobs at his firm. However, he finds out soon after that he has been promoted to a junior copy writer since his boss thinks he's too good (and too old) to be an assistant.

Rachel goes to work with Joey to watch him do a love scene on Days of Our Lives, and later has a romantic dream about him. She consults Monica, and decides that she doesn't have a thing for Joey, she has a thing for Drake Ramoray, but questions this decision later when Joey talks about how he was in love with her. Monica is proud when her restaurant is booked solid for the next month, but when Phoebe uses the opportunity to play guitar for the restaurant patrons, Monica tells her friend that her music isn't classy enough for her restaurant. Phoebe and Monica feud, insulting each other's music and cooking, until they realize that they're both being silly and apologize to each other. Chandler plans a romantic getaway in a bed and breakfast in Vermont for him and Monica, but when Monica is stuck at the restaurant, he and Ross go instead. When the hotel totally rips Chandler off, he gets pissed, and he and Ross, who is high on maple candy, steal as much "free stuff" from the hotel as they can get their hands on.

Joey tries to trick his friends into going to a one-woman play while he secretly throws a party on the roof for his Days of Our Lives friends. Everyone finds out about Joey's duplicity except for Chandler, who ends up attending the horrible play by himself. Monica makes a complete ass of herself when she meets all the soap opera stars at Joey's party. Ross gets a new co-worker, a beautiful and brilliant female paleontologist named Charlie, and is immediately attracted to her, but he's intimidated by her Nobel laureate ex-boyfriends. Rachel, who can't deny her attraction to Joey, decides she's going to tell him how she feels, and Ross decides to make a move on Charlie, but Ross and Rachel are surprised to find Joey and Charlie lip-locked in the corner.

Without telling their friends, Monica and Chandler go to get fertility tests and run into Janice at the doctor's office. The couple is devastated when they find out that they both have fertility problems. Although Ross is still a bit bitter about losing Charlie to Joey, he helps Joey act smart enought to talk to Charlie, and even encourages Charlie to stay with Joey when she has her doubts about the relationship. Phoebe makes Rachel promise not to get a massage at a big corporate-runspa even though she has a gift certificate. Both friends are busted when Rachel breaks her promise and goes to the spa, only to find that Phoebe, who is so against spas like this, actually works there because the money is good.

At Joey's urging, Rachel takes Charlie shopping for new clothes. Phoebe tags along because she's going to a party that night where she knows she's going to see Mike, and she wants to get a new dress. In the dressing room, Phoebe and Rachel talk about how Rachel feels about Joey, and Charlie overhears. Rachel is devastated, until it becomes clear that Charlie mis-heard and thought that it was Phoebe that had the crush on Joey. Rachel doesn't correct her. Phoebe, in her amazing new dress, runs into David, who is back in New York from Minsk, and she decides to go out with him instead of going to the party. Monica and Chandler decide to look for a sperm donor, and Chandler brings home a handsome coworker as an option. Chandler and Monica completely freak out Chandler's coworker by asking strange family history questions, and then later decide that they would actually prefer to adopt. Ross is up for keynote speaker at a paleontology conference in Barbados, but when his one-man audience at his audition falls asleep, he thinks fast and tricks the old man into giving him the job.

The whole gang goes to Barbados for Ross's keynote speech at the paleontology conference. Phoebe brings David, but accidentally calls him Mike. David decides he should propose to her since she broke up with Mike because he didn't want to get married. Monica realizes that Phoebe still has feelings for Mike and calls Mike, who shows up and proposes to Phoebe in the middle of David's proposal. Phoebe says she doesn't want to marry him right away, but does love him and want to be with him. David bows out gracefully. Rachel continues to pine after Joey, as Charlie and Ross bond over recreating his speech after his computer eats it. Monica has big hair problems in the humidity.

Because of the constant rain, Monica and Mike end up in a ping pong battle. Phoebe is turned on by Mike's competitive side. When Monica hurts her hand, Chandler takes over for her because he knows how important it is to her to win, and he beats Mike in a sudden death match. Joey and Charlie finally realize they have nothing in common and break up. Rachel admits to Joey that she has feelings for him, and he says he still has feelings for her, but they can't be together because of Ross. Charlie admits to Ross that she has feelings for him, and Ross tries to fight his feelings for her because of Joey, but fails. After Joey sees Charlie and Ross kissing, he goes to Rachel's hotel room and kisses her. Rachel is very happy that Joey changed his mind.