Chandler and Phoebe shop for a ring for Monica. Chandler finds the perfect one, but Phoebe accidentally lets it get away. While Chandler is busy with getting the ring back, Joey and Ross are lead to believe that he's mad at them, so they decide to team up and give him a cold shoulder treatment. Rachel continues to date Paul and wants him to open up to her, however, he opens up a bit too much.
While visiting an art museum, Monica puts her name on a two-year waiting list to use the museum for a wedding. Accidentally Chandler finds out about this and freaks out. Meanwhile, Paul threatens to have Ross fired from the university if he continues to date Elizabeth, however, that doesn't stop the two of them from going to her dad's mountain cabin over the weekend. Unfortunately for them, Paul has the same idea to bring Rachel there.
Ross meets Elizabeth's father for the first time and unfortunately he takes an instant disliking to Ross. However Paul does hit it off with Rachel and she tries to talk Ross up but does so with mixed results. Joey almost gets fired from "Mac and C.H.E.E.S.E." after offending the operator of the robot. Meanwhile, Phoebe writes a book based on Monica and Chandler.
Joey gets an audition for the lead character in a new TV show. When the audition is rescheduled, Chandler takes the message but forgets to tell Joey. When Joey misses the audition, he gets upset and the group reminisces about their mishaps in the past.
After Joey's fridge breaks, he tries to cajole his friends into helping him buy a new one. Meanwhile, Ralph Lauren is organizing a charity ball and Rachel looks for a date, however, unexpectedly it turns into a competition between Monica & Chandler against Phoebe for finding the best candidate. Ross continues to date Elizabeth, but he gets nervous when she makes plans for a spring break at Daytona Beach.
At the end of semester Ross gets his student evaluations and one of them writes that he's hot. It turns out to be a cute girl named Elizabeth and even though it could cost him his job, Ross considers dating her. An ex-girlfriend of Chandler's from college is directing the new Al Pacino movie and Joey asks Chandler for help with getting an audition. Meanwhile, after a fire ruins Phoebe and Rachel's apartment, they're forced to find temporary living spaces with Monica and Joey.
Joey tries to earn some extra money by entering a medical study, however, there's a slight problem: the study is for identical twins. Rachel and Phoebe take self-defense classes, but Ross attempts to give them a lesson in Unagi instead. Meanwhile, Chandler and Monica agree to give each other homemade presents for Valentine's Day.
Barry and Mindy's impending divorce prompts the gang to fantasize about what their lives might be like if they'd all taken different courses. Ross is still married to Carol, and Rachel is married to Barry, but fawning over famous soap star Joey Tribbiani. Monica is still fat and dating a doctor. Chandler is an aspiring writer and Phoebe is a Wall Street shark for Merrill Lynch.
The gang continue to fantasize about how different their lives could have been. Carol and Ross decide to have a threesome to spice up their marriage. Rachel goes to Joey's but is incredibly nervous about cheating and gets drunk. Meanwhile, Monica's dinner date falls through and Chandler tries to cheer her up but things take an unexpected turn.
Chandler admits that he hasn't cried since he was a child. Phoebe discovers that Ursula is starring in porno movies using her name. Rachel desperately tries to stop Ross and Jill from starting a relationship.
Joey gets in trouble for giving attractive female customers free food at Central Perk. A sick Monica desperately tries to convince Chandler that she's not sick. After her father cuts her off, Rachel's sister Jill comes to town. Rachel encourages her to start an independent life by finding a job and an apartment, but one thing leads to another and Jill ends up asking Ross out on a date. Even though Rachel doesn't want to admit it, she clearly isn't okay with that…