Chandler plans to propose to Monica at dinner, but his plans go awry when Richard shows up at the same restaurant. Meanwhile, Phoebe and Joey join Rachel at a charity auction only to discover that Joey isn't aware what a silent auction is. And Ross and Elizabeth's relationship comes to a crossroad. Chandler continues to pretend to hate the idea of marriage, unaware that Richard wants Monica back. Meanwhile, Rachel and Phoebe discuss their 'back-up' plans, if they are not married by the time they're 40.
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.
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.
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...
Rachel orders an apothecary table from Pottery Barn, which is a problem because Phoebe hates the mass-producing company. After Janine and Joey double date with Chandler and Monica, Janine tells Joey that she thinks the other two are boring. Ross buys a new apothecary table too, which causes problems for Rachel. After a confrontation with Monica and Chandler, Joey breaks up with Janine and she moves out.
Janine gets an invitation to dance on "Dick Clark's New Year's Rockin' Eve" and she invites Joey, Monica and Ross to join her. Being huge fans of the show, Monica and Ross get overly excited. At the taping, Joey tries to kiss Janine at midnight and Monica and Ross resurrect their dance routine from high school. Meanwhile, Rachel, Phoebe and Chandler look for Monica's Christmas presents.
It's Thanksgiving and Monica's parents are coming to visit, which is a problem because, not only they do not like Chandler, they also don't know that he and Monica are living together. Rachel is tasked with making a Thanksgiving dessert, but she does so with mixed results. Meanwhile, Joey and Ross are eager to finish the dinner and leave, because they want to go to a Thanksgiving party with Janine and her dancer friends.
Now roommates Phoebe and Rachel decide to start running together, but Rachel is embarrassed by Phoebe's odd running style. Joey finds a sexy new female roommate and tries very hard not to flirt with her. Meanwhile, Chandler decides to surprise Monica by cleaning the apartment, but forgets where everything goes. Ross tries to help him remedy the situation.