Rachel, who left her fiance at the altar on her wedding day, has come to New York and ends up living with Monica as her roommate when Phoebe had just moved out. It establishes early on in the season that Ross has been infatuated with Rachel since the two characters attended high school. Several episodes revolve around his attempts to tell her how he feels. Ross leaves for a fossil dig in China at the end of the season, missing out on Rachel's birthday party but staying long enough to give her a meaningful present: a cameo that was just like the one that belonged to Rachel's grandmother. Chandler accidentally reveals that Ross is in love with Rachel, much to her shock. Rachel realizes that she has feelings for Ross and rushes off to the airport to tell him that she wants to pursue a relationship with him. As she waits at the gate for Ross to arrive, the season ends on a cliffhanger as he gets off the plane but with a new girlfriend: Julie.
Ross' estranged lesbian wife, Carol Willick, is pregnant with his baby. This puts him and Carol's lesbian life partner, Susan Bunch, in an awkward position. When the baby is born at the end of the season, Ross, Carol, and Susan agree to name him Ben: after a name tag on a janitor's uniform worn by Phoebe.
The episodic nature of the season sees the other characters having multiple dates, many of which go wrong (Monica dates a minor in one episode). The recurring character of Janice is introduced as a girlfriend Chandler breaks up with in an early episode but frequently returns to through the ensuing ten seasons.
- Jennifer Aniston as Rachel Greene
- Courteney Cox as Monica Geller
- Lisa Kudrow as Phoebe Buffay/Ursula Buffay ("The One With Two Parts, Part 1"/"The One With Two Parts, Part 2")
- Matt LeBlanc as Joey Tribbiani
- Matthew Perry as Chandler Bing
- David Schwimmer as Ross Geller/Russ
- Anita Barone as Carol Willick ("The One With The Sonogram At The End")
- Jane Sibbett as Carol Willick
- Maggie Wheeler as Janice
- Mitchell Whitfield as Barry Farber
- Cosimo Fusco as Paolo
- Jessica Hecht as Susan Bunch
- Up until "The One Where Underdog Gets Away", Monica and Rachel lived in apartment 5, and Joey and Chandler lived in apartment 4. However, it was realized that such low numbers would correspond to apartments on a lower floor, while their apartments were clearly seen to be higher up in the building. Thus the numbers were changed to 20 and 19 respectively.
- However, in "The One With The Dozen Lasagnas", Monica and Rachel's apartment door number is 5 and Chandler and Joey's apartment door number is 4.
- Visible in Monica's apartment is a billboard (stuck on top of a theatrical poster) promoting the Bijou Theatre. The only Bijou theatres open at this time is the New York East Village Club 82/Bijou Cinema gay adult theatre, located on the eastern edge of Greenwich Village where the apartments are supposed to be located.
- Despite the apartments supposedly being in Greenwich Village, later episodes give the address as 495 Grove Street which is actually in Brooklyn.
"The Pilot" ("Monica Gets A New Roommate") [#1]
w: Marta Kauffman & David Crane, d: James Burrows, a: 09/22/1994
Monica and the gang introduce Rachel to the "real world" after she leaves her fiancé at the altar. Ross struggles with his rediscovered feelings for Rachel.
- "The Pilot"
- "The One With The Sonogram At The End"
- "The One With The Thumb"
- "The One With George Stephanopoulos"
- "The One With The East German Laundry Detergent"
- "The One With The Butt"
- "The One With The Blackout"
- "The One Where Nana Dies Twice"
- "The One Where Underdog Gets Away"
- "The One With The Monkey"
- "The One With Mrs. Bing"
- "The One With The Dozen Lasagnas"
- "The One With The Boobies"
- "The One With The Candy Hearts"
- "The One With The Stoned Guy"
- "The One With Two Parts, Part 1"
- "The One With Two Parts, Part 2"
- "The One With All The Poker"
- "The One Where The Monkey Gets Away"
- "The One With The Evil Orthodontist"
- "The One With The Fake Monica"
- "The One With The Ick Factor"
- "The One With The Birth"
- "The One Where Rachel Finds Out"