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Friends is one of the most beloved sitcoms of all time. Part of its allure is the fact that all six characters were so benignly imperfect. Monica Geller, Ross Geller, Rachel Green, Chandler Bing, Phoebe Buffay, and Joey Tribbiani tripped and stumbled through life for 10 seasons. Their romantic blunders were perhaps the most relatable. Do you remember the biggest romantic misstep each character made?

Rachel Green didn’t realize her ex-fiancee looked like Mr. Potatohead until the wedding day 

Rachel’s biggest dating mistake may have happened before the start of Friends. In fact, the entire show’s premise was based on Rachel’s biggest romantic blunder. In the pilot episode, Rachel ran away from her wedding mere moments before walking down the aisle. She hightailed it to Monica’s apartment, hoping to find her there, then was sent to the Central Perk, where she ultimately met all her new pals. 

A scene from the pilot episode of friends, featuring Ross and Rachel, Monica and Phoebe
‘Friends’ pilot episode | NBCU Photo Bank

Within moments of meeting most of the gang, Rachel shared the wild revelation that sent her running for the hills. She revealed that she realized Barry Farber looked strikingly like Mr. PotatoHead. The fact that Rachel made it to the wedding day without the realization is perplexing. It all worked out in the end, though. 

Monica Geller left an outgoing message on Richard Burke’s answering machine telling the world she was getting her period 

Monica Geller’s search for the perfect mate ended when she decided to give Chandler Bing a chance. Before the friends dated, Monica was head over heels in love with Dr. Richard Burke. While Chandler and Monica fans insist the couple was the ultimate endgame couple of the series, there is evidence to suggest Dr. Burke could have been the one. 

Monica was so distraught over their breakup that she even dialed into his answering machine to listen to his messages, fearing he may have met someone else shortly after their separation. That decision was terrible, but what came next was worse. In her haste to improve a bad situation, she left an outgoing message on his machine, informing him and anyone who called him that she was acting erratically because she might have been getting her period. Monica and her friends were, rightfully, horrified. 

Ross Geller dated a college student 

Ross didn’t have good judgment when it came to relationships. His first serious romance resulted in a marriage, but his wife, Carole Willick, later realized she was gay. From there, Ross dated Julie but dumped her to be with Rachel. He sort-of cheated on Rachel and followed that up with a string of failed romances, another short-lived marriage, and odd dates. 

Matthew Perry as Chandler Bing, David Schwimmer as Ross Geller, Matt LeBlanc as Joey Tribbiani in 'Friends'
Matthew Perry as Chandler Bing, David Schwimmer as Ross Geller, and Matt LeBlanc as Joey Tribbiani | Chris Haston/NBCU Photo Bank

Ross’ biggest romantic blunder was his inexplicable decision to date his student. While teaching at NYU, he started hooking up with Elizabeth. While Ross tried to convince everyone that the relationship wasn’t weird, it was. Things ended poorly, as was expected. 

Joey Tribianni threw a girl’s leg into a fire 

Joey Tribbiani was a nice guy in many ways, but he was pretty awful to the women he dated. He left a string of broken hearts and women who never got a return call in his wake. Still, most of Joey’s romantic endeavors were pretty casual. Still, his worst relationship error was pretty big. He threw a woman’s prosthetic leg in a fire and never called her again. 

In the season 3 episode, “The One With Phoebe’s Ex-Partner,” Joey attempted to avoid a woman he previously dated but refused to tell his pals why. Eventually, he revealed that he and Ginger initially hit it off, but he disappeared from her life when he accidentally threw her prosthetic leg into a burning fire. It was an accident, but the action certainly warranted an apology phone call. 

Phoebe Buffay dated a creepy psychologist and didn’t realize how creepy he was 

Phoebe’s biggest dating mistakes played out in front of Friends audiences. While the unassuming Phoebe was almost perpetually unattached, she did have a few notable bad dates. Her worst date may have been the creepy psychologist. 

In the season 1 episode, “The One With the Boobies,” Phoebe introduced her boyfriend, Roger, to her friends. The psychologist systematically broke down each member of the gang, uncovering their past trauma and then walking out of the apartment as if nothing had happened. Roger wasn’t just unaware; he was downright strange. Phoebe didn’t realize anything was amiss until he freaked out on her over being rejected by the friend group. 

Chandler Bing hooked up with one of Joey’s sister, but couldn’t remember which one 

Liquor has a way of making people do things they wouldn’t normally do. During a party, Chandler, distraught by a recent breakup, got incredibly drunk. His lack of inhibition led him to hook up with someone. That would have been fine if only it hadn’t been one of Joey’s many sisters. 

Monica Geller, Chandler Bing and Richard Burke sit down for dinner together in season 9 of 'Friends'
Monica Geller, Chandler Bing, and Dr. Richard Burke | Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty Images

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Joey, the only boy in his family, was particularly protective of his sisters. Still, he could have dealt with Chandler and his sister dating, but Chandler didn’t want to date Mary Angela. He couldn’t even remember which sister was Mary Angela. The situation was messy.