The One Where Ross Can't Flirt
Season 5, episode 19
116th overall episode of Friends
Ross trying to flirt with Caitlin.
Episode Information

April 22, 1999

Written by

Doty Abrams

Directed by

Gail Mancuso

Episode Guide

The One Where Rachel Smokes


The One With The Ride-Along


"The One Where Ross Can't Flirt" is the nineteenth episode of the fifth season of Friends, which aired on April 22, 1999.


Chandler, dressed up for his and Monica's ten-month anniversary, picks up the pizzas that hot delivery girl Caitlin has brought for the group, but Ross mistakes his friend's natural jokes for flirting. Chandler denies this. Ross ends up telling the friends what Chandler did. Phoebe points out that the real reason Ross is mad is because he finds Caitlin attractive, and Ross takes the opportunity to flirt with her when he finds a missing vegetarian pizza that wasn’t delivered for Phoebe. Unfortunately, flirting is not his best quality, and this he shows with inappropriate comments he makes to Caitlin and embarrasses himself. Saddened by this, Ross orders yet another pizza, practicing flirting on Phoebe as the pizza is on its way (Phoebe doesn't get that Ross is flirting). Caitlin arrives with the pizza, but Ross screws up the flirting again and ends up talking to her about gas and methane and embarrasses himself again. He scares her so much that she pays for the pizza herself and flees the apartment. Out of pity for Ross, Rachel catches up with her and tries to talk her into going out with Ross. Rachel returns to the apartment and gives Ross Caitlin's phone number.

Rachel tells Caitlin that Ross was trying to flirt with her.

Meanwhile, Joey introduces everyone to his Italian grandmother, who is deeply intent on seeing her grandson debut on Law & Order. As she doesn't speak a word of English, they find it difficult to communicate with her, except for Phoebe, who manages to offer her a glass of water in Italian. The TV show starts, but Joey finds out that he's cut out of it. Desperate not to kill his grandmother of shock, he records himself on tape at his apartment in a crime scene where he holds his duck hostage. The clip is pretty crude, as he doesn't even change the sweater he's wearing. But the clip is good enough for Nonnie - that is, until the video tape continues rolling, showing Chandler sing Space Oddity in front of the camera.

Monica, who is getting dressed for the big anniversary date, asks Phoebe to return her the earrings Chandler bought her, which Phoebe borrowed some time ago. It turns out, however, that Phoebe lent the same earrings to Rachel, who has lost one of them. Phoebe tells her how the earring are Monica's, which makes Rachel flip out because she's not allowed to borrow Monica's stuff as she ends up losing it. Fearing that Monica will kill her if she finds out, Phoebe takes the blame instead of Rachel, but Monica is understanding with her. Rachel steps in and explains everything to Monica, who immediately loses it with Rachel. Monica ends up wearing another pair of different earrings, which luckily for her, Chandler doesn't notice. Monica and Chandler leave for dinner, and Chandler thanks Ross for the earrings he picked up for Monica. 

Cast and Crew

Main Cast

Jennifer Aniston - Rachel Greene
Courteney Cox - Monica Geller
Lisa Kudrow - Phoebe Buffay
Matt LeBlanc - Joey Tribbiani
Matthew Perry - Chandler Bing
David Schwimmer - Ross Geller

Supporting Cast

Kristin Dattilo - Caitlin
Lilyan Chauvin - Nonnie


Directed By:
Gail Mancuso

Written By:
Doty Abrams


  • The drawing on the Magna-Doodle is of the New York skyline.
  • Ross looks at Rachel before continuing his description of Caitlin and she says it's OK for them to see other people but as he starts to describe her it's obvious Rachel's not really OK.
  • Rachel mentions that it took Ross nine years for him to start dating her. When Ross fails in his flirting with Caitlin, he dejectedly closes the door and says "that's OK, in nine years we'll be right there". This is clearly aimed at Rachel who made the cruel remark earlier. (In fact he and Rachel will have been remarried for around 4 years by then).
  • The movie Joey's grandma mentions, "Capricorn One", which stars Elliot Gould, who plays Jack Geller on Friends.
  • During Ross' disastrous flirting, Chandler exclaims "Oh the Humanity" which may be a reference to the famous news commentary of the Hindenburg disaster.
  • Since Caitlin is never seen again, it's unknown if she and Ross did ever go out.
  • Chandler is seen singing the David Bowie song Space Oddity in this episode. While travelling back from Las Vegas with Phoebe, Joey starts to sing the same song in The One After Vegas.


  • Chandler mistakes Joey's grandmother for the one who speaks English, but he has met the other grandmother before in "The One Where Chandler Can't Remember Which Sister". Although they only met once and for a brief time, so it's possible he doesn't remember her.
  • In this episode, Phoebe can speak fluent Italian. However, in "The One with The Blackout" she can't understand what Paolo is saying. Although, it is possible that she picked up some Italian in the four years since Season 1.
  • When Rachel says "We don't need her measurements." in this shot, Ross' hands are up, but in the next shot, his right hand is on the chair.
  • When Rachel is talking to Caitlin on the street, at the top right corner of the widescreen version of the show, two background actors can be seen holding their positions until they are allowed to walk.
  • Caitlin would likely be fired from her job as she is not allowed to date a customer while on duty so Ross would have had to wait until her shift was over to ask her out.
  • Chandler is known for not being able to talk to women in past episodes but he easily "flirts" and makes small talk with the pizza girl in this episode. Although he may not be nervous anymore because he is already in a relationship.
  • When Joey brings in his grandmother, he introduces her as the one who does not understand a word of English and later Chandler too says, "she doesn't know hello..", But still through the episode they all keep talking to her in English and she keeps responding too.
  • In the first scene when the duck walks around the quack sounds are not synchronized with it opening its beak.
  • Monica gets upset at Rachel for losing one of her earrings, explaining why she doesn't lend her jewelry to Rachel, but Rachel had borrowed the earrings from Phoebe, not knowing originally who they belonged to, and it wouldn't appear to make sense why Monica would be upset towards Rachel for losing them as opposed to being upset at Phoebe for lending something of hers to someone else without permission beforehand.
  • Ross is both right and wrong. Natural gas is indeed odorless and an additive is added for people to be able to detect leeks. However Ross later says "methane smells" and this is incorrect -- pure methane is an odorless gas -- the main constituent of gas used in homes and businesses. This is exactly the gas that he is referring to when he tells Caitlin that "they put the smell in".


External links

Episode Navigation

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Preceded by
"The One Where Rachel Smokes"
The One Where Ross Can't Flirt Followed by
"The One With The Ride-Along"
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