Second Look: Friends Season 5, Episode 19 – “The One Where Ross Can’t Flirt”

I always wish Friends had utilized bottle episodes more frequently in the first half of its run, when its characters and stories were a bit more creatively dynamic; “The One Where Ross Can’t Flirt” is only the second episode of its kind in the first five seasons of the series (the first being “The One Where No One’s Ready”, of course), where as the second half of the series has a whopping nine bottle episodes to its credit. It’s just a bummer Friends didn’t utilize the storytelling device more frequently when it could, rather than when it clearly needed to, in order to preserve budget in later seasons, because “The One Where Ross Can’t Flirt” is a mid-season pleasure, an episode that balances its silliness and weightlessness with an incredibly momentum-driven script, turning Monica’s apartment interior into a fun little stage play for a goofy story about the man boys of the Friends sextet.

“The One Where Ross Can’t Flirt” is set on what is supposed to be the night of Joey’s debut on Law & Order, which he has invited his frail Italian grandma (played by the lovely Lilyan Chauvin, who you can read a bit more about below) over to watch with the group in Monica’s apartment. But before we can even get to Joey’s unfortunate foray into primetime TV, “The One Where Ross Can’t Flirt” opens its proverbial can of worms when Chandler receives a pizza order for the party, and has some friendly candor with delivery woman Caitlin (whose new haircut she thinks makes her look like an “eight year old boy”), setting the stage for an incredibly awkward Ross plot – but one the series surprisingly doesn’t completely compromise his character for, leaning back into the awkward, stilted nature of Ross’s interactions with women that defined him before his relationship with Rachel.

Thankfully, Ross being awkward and Joey scrambling is not the only hook of the episode: as with the show’s terrific previous foray into bottle episodes, “The One Where Ross Can’t Flirt” keeps itself busy with a few fun, flittering subplots that keep themselves spinning around Joey and Ross’s core conflicts at the heart of the episode. Honestly, my favorite plot of the episode surprisingly comes from Monica, who keeps the women of the episode busy on a jewelry hunt (for an earring gifted to her from Chandler) as she gets ready for her 10-month anniversary date. Even though the story is really just a silly chain of event revealing a tangled web of borrowed items between the three women, “The One Where Ross Can’t Flirt” uses this story to give the episode some shape, as the blame shifts from one character to the next, as they try to unwind the trail of what happened to Monica’s earring – and eventually, shift into a plan to try and hide it from the incredibly oblivious Chandler.

Although it all blends for what makes for an incredibly light episode, there’s an undercurrent of Friends examining the fragile male ego of the late 1990s in its various forms that I quite enjoy. In each of their own ways, the stories of “The One Where Ross Can’t Flirt” are about male hubris; Joey’s pride about showing his grandmother he is successful, Ross being unwilling to recognize his own shortcomings at anything (a trait we’ve seen encouraged by his parents in the past) – and Chandler’s inability to understand women in any capacity, as he argues with Monica over the differences he perceives between men and women flirting.

All three of these stories lead Friends into very different directions, though working towards the same observations; with Ross, “The One Where Ross Can’t Flirt” becomes a cringe comedy, as he talks about methane gas and liking children in his misguided attempts to flirt with Caitlin. With Chandler, Friends leans into the slapstick, relying on Monica’s incredulous reactions to Chandler’s rambling bullshit as a backbone for the episode’s comedy – and of course, through Joey, “The One Where Ross Can’t Flirt” maintains a sense of heart, as Joey tries to scramble to find a way to get himself into an episode of television he’s been cut out of, eventually recording over (mostly, at least) Chandler’s self-recording of him singing “Space Oddity”, so he doesn’t disappoint his Nonni after realizing his role was cut out of the episode (and his attempts to convince her he was Sam Waterston failed).

Unsurprisingly, an episode mostly about male fragility ends up spending a lot of time with the women of Friends, and how they acquiesce to the men around them. And it’s here where “The One Where Ross Can’t Flirt” falters a little bit, specifically with Rachel – with Monica at least, her attempts to massage Chandler’s ego come from a place of not wanting to disappoint him, by revealing the dirty little jewelry exchange program hiding behind everyone’s back. But with Rachel, seeing her feel empathetic towards Ross and his bad flirting, and then going outside the building to chase down Caitlin and convince her to give Ross a chance is… a bit weird, and one whose awkwardness is not waved away by Rachel’s comment to Caitlin about them needing to have “a long talk” later on (one that would obviously never come, given we never see Caitlin again). It’s an odd gesture – and one that Ross certainly hasn’t tried to return in any way, especially post-London.

Had “The One Where Ross Can’t Flirt” arranged itself more from Rachel’s POV, her journey to accepting the new status quo of her relationship with Ross might make some sense; here, it just feels like the writers fishing for something that isn’t there, trying to stir up some audience interest in hopes of engineering interest towards a season finale twist (which is certainly lying in wait in “The One in Vegas”, but is not grounded by anything that happens in this episode). Utlimately, it just feels cheap for Rachel’s character, undercutting her own emotional journey and independence as we watch her cater to Ross’s emotional needs and wants yet again (something that was a sticking point in their actual relationship, no less).

Rachel’s weird third act decision aside, “The One Where Ross Can’t Flirt” is a great way for Friends to bide its time in the amorphous space between the post-holiday sweeps weeks and the impending season finale, an episode that embraces a small, weightless story in order to explore and reinforce some familiar character traits (some endearing, some annoying – it actually strikes a pretty strong balance, without ever becoming a grating, unfunny episode). Most of all, it feels like a writer’s room having fun with something other than a Big Episode (like a season finale or milestone episode, like “The One Hundredth“) as it reaches the halfway point of the series, something that would become an unfortunate rarity in the second half of the Friends oeuvre.

Other thoughts/observations:

• Just want to take a moment to appreciate Lilyan Chauvin, whose 60-year career in the United States – who not only had over 100 film and TV acting roles to her credit, but was an acting and director professor, a VP on the Women in Film council, AND also directed television episodes and stage plays (all while fighting breast cancer for the last 40 years of her life). And small spoiler: this won’t be the only time we hear her name at Processed Media in 2026 (deets to come!).
  
• “You wanna see flirting? I’ll show you flirting!” Ross is never one to make threats.
  
• “See? Vegetarianism benefits everyone!”
  
• Apparently Phoebe speaks Italian!
  
• I do wish this episode would’ve spent a little more time exploring how different Monica treats Rachel and Phoebe, after exploding on Rachel for losing the earring (that she was lent by Phoebe, who originally borrowed it from Monica).
  
• Rachel points out Ross is bad at flirting: “We met, you flirted, then Bam! – nine years later, you had me!”
  
• Chandler, amazed at Joey’s Nonni: “she doesn’t know hello, but she knows Capricorn One?”
  
• “We have seven people and like ten pizzas, what did you think?” Caitlin: “I thought Joey was there.”
  
• The reveal that Ross picked out the earrings Chandler bought Monica is both funny, and a bit unsettling.
  
• Up next: Rachel makes a choice in “The One with the Ride-Along”.

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