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VOICE OVER: Emily Brayton WRITTEN BY: Sammie Purcell
We weren't there for these unforgivable "Friends" moments. For this list, we'll be looking at the worst moments from this beloved sitcom that, upon rewatch, we just can't let go. Our countdown includes Fun Bobby, the list, the manny, and more!

#10: Joey’s Dumbing Down Various

Also in:

Top 10 Best Joey & Phoebe Moments on Friends

Let’s face it – as much as Joey is a beloved character on “Friends,” the writers room did him significantly dirtier as time went on. In addition to having Joey’s friends make fun of any of his interests that might be more associated with femininity, the writers also turned him from a lovable babe to just plain dumb over the show’s run. It might be funny to watch Joey struggle to learn French, or to hear him confuse the word “moot” for “moo,” but a lot of these moments don’t really jive with his character as originally intended. Looking back, it sort of stinks that the writers traded in his depth for easy laughs.

#9: Fun Bobby “The One With Russ”

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Top 10 Most Unforgivable '90s TV Moments

We should celebrate all cases of someone with an alcohol addiction overcoming that issue. Unfortunately, “Friends” didn’t really hit the mark on this one. In its early seasons, one of Monica’s boyfriends nicknamed “Fun Bobby” suddenly reveals himself to be not all that fun. Turns out, Bobby has an alcohol problem, and many of his entertaining antics were a result of that. Once he’s sober, his personality completely changes. It’s not that he becomes sad, which might make sense – it’s more like he starts holding dull conversations about hardware stores. “Friends’” portrayal of the challenges someone faces when becoming sober really aren’t all that funny, now that we think about it.

#8: The List “The One With the List”

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Top 10 Most Unforgivable Moments in Sitcoms

Everyone remembers the iconic moment in “Friends” where Rachel and Ross finally kiss. After that unforgettable development, Ross has a choice to make – be with Rachel, or continue to be with his then-girlfriend, Julie. In an amazingly boneheaded moment, Ross decides to make a pros and cons list about dating both women. Of course, Rachel finds this list, in which Ross calls her spoiled, ditzy, and insults her job. For someone so close to finally dating the person he’d been enamored with for so many years, he sure screwed the pooch on this one.

#7: Ross’ Jealousy “The One With All the Jealousy”

Also in:

Top 10 Monica & Ross Sibling Moments on Friends

In what might just be all of sitcom history, there aren’t many characters as insecure as Ross Geller – and even fewer who are more likely to let it get the best of them. When Rachel gets a job at Bloomingdale’s, she’s ecstatic to finally be working in the fashion world. Ross, unfortunately, lets his jealousy over her new attractive co-worker, Mark, overshadow any support he had for her. Ross’ jealous nature in general is a pretty bad look, but he goes way over the top during this story arc. It’s clear he doesn’t trust Rachel, which is one of the many reasons they don’t work out right away.

#6: Paolo’s Abhorrent Behavior “The One With the Dozen Lasagnas”

Some things just don’t deserve a light, humorous spin. In season one of “Friends,” Rachel has an Italian boyfriend named Paolo. He seems harmless enough, but one day he shows up to Phoebe’s massage parlor, and things go horribly wrong. Paolo assaults Phoebe and exposes himself to her – all while a laugh track plays in the background. When Phoebe tells Rachel, she seems nervous that Rachel won’t believe her and frames it as Paolo merely “making a pass” at her. Her hesitation and playing down the severity of it all feel pretty true to how a victim might come forward. What’s messed up is, again, the inclusion of that intermittent laugh track as Rachel is told about the situation.

#5: The Manny “The One With the Male Nanny”

Also in:

Top 10 Funniest Friends Moments You Forgot About

And once again, we find ourselves coming back to Ross – we’re sensing a theme here. One of Ross’ weirdest character flaws is his obsession with gender norms. Early on in the show’s run, he flips out over his son Ben’s decision to have a Barbie as a toy, but the subject of this entry comes a bit later. After Rachel and Ross have their daughter, Emma, they start an arduous search for a nanny. Enter Sandy: a childcare professional who seems to have everything the couple is looking for. There’s just one issue – he happens to be a man. Ross has an annoyingly hard time getting over the idea that a man could want to be a nanny.

#4: Joey Proposing to Rachel By Accident “The One Where Rachel Has a Baby”

Okay, was the entire writers room was asleep at their desks for this one? Before Rachel gives birth to Emma, Ross’ mom gives him his grandmother’s engagement ring and urges him to propose to Rachel. The ring is eventually left in Rachel’s hospital room, in Ross’ jacket pocket. A mishap causes Joey to pick up the ring – on one knee of course–leading Rachel to think he’s proposing. And she…says yes? Confusion ensues. Our issue with this storyline is that it just lasts way too long. No one would ever let somebody believe that they had proposed to them if they didn’t mean to – not even someone as dumb as the show wants us to think Joey is. Bad writing all around.

#3: Ross Trying to Bang His Cousin “The One With Ross and Monica’s Cousin”

This is our last Ross entry (we promise), but boy is it a doozy. Among his other faults, Ross seems to have a bit of an issue with kissing family members. We cringed to the high holy heavens when we found out that he was Monica’s “Midnight Mystery Kisser,” [xref], but at least that was an accident! This one was wholly on purpose. When Ross and Monica’s cousin comes to visit, no one can keep their eyes off of her – including Ross himself. When Ross and Cassie are watching television, he somehow convinces himself that kissing her would be a good idea – to obviously disastrous effect.

#2: Monica’s Weight Various

Also in:

Top 10 Funniest Monica Moments on Friends

“Friends” has been pretty prejudiced on more than one occasion – something we’ll get to shortly – and it’s fatphobia is right up there with things that are just not okay. The show even went so far as to fat shame kids sometimes, but the thing we all remember is the show’s treatment of Monica’s weight when she was younger. Not only was Monica’s weight used for laughs, it was usually just plain mean. In addition to that, it was often used as a way to show us how much “better” Monica had become simply by getting thin. It’s a terrible lesson to impart about health and body image, and the fat jokes got old pretty quick. Before we unveil our top pick, here are a few honorable mentions. Shark…Intimacy, “The One With the Sharks” Seriously? We’re Not Even Sure We Can Get This One Past the YouTube Censors! The Secret Marriage, “The One Where Joey Loses His Insurance” Pro Tip: Always Check Your Marriage Records Ross Dating a Student, “The One Where Ross Meets Elizabeth’s Dad” Run, Elizabeth! Run Far Away!

#1: Transphobia & Homophobia Various

Here we are folks! The worst of the offenders. It seems that “Friends” really had no idea what to do with the problem of Chandler’s parent – besides making bad jokes and being homophobic, that is. In 2022, show co-creator Marta Kauffman addressed how poorly handled the storyline was, calling it a mistake. The character, eventually played by Kathleen Turner, had come out as gay while Chandler was young, garnering resentment for breaking up the family. Later going by the professional name “Helena Handbasket” at her Las Vegas drag show, it takes Chandler a good while to get over their estrangement, and the journey there isn’t the most graceful. While a lot of “Friends” has aged well, this is one arc that would have been handled differently if made today.

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