The main characters in Friends dated a variety of people before they settled down with their “lobsters”, but in Phoebe Buffay’s case, the writers used the same story in two of her relationships, and both were very creepy. The 1990s saw a bunch of sitcoms that went on to become classics, but the one that continues to be regarded as one of the greatest TV shows of all time is Friends, created by David Crane and Marta Kauffman. Friends continues to have a solid fanbase (that has expanded thanks to its arrival in the world of steaming), but the constant rewatches have brought to light some of the show’s biggest problems.

Friends took the audience to New York City to follow the lives of a group of six young adults doing their best every day to juggle their social, personal, and professional lives while also dealing with everything adulthood threw at them. Over the course of 10 seasons, viewers followed Monica, Chandler, Phoebe, Joey, Rachel, and Ross through many ups and downs and saw them deal with a number of problems, with a special focus on their personal lives. Each of them dated various people throughout Friends, and while most of them weren’t bad people or toxic relationships, in some cases there were certain patterns that shouldn’t have been repeated.

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Such is the case of Phoebe, who before she met her husband, Mike Hannigan (Paul Rudd), dated a variety of guys, but the writers of Friends repeated the same story in two of her relationships, and it was a controversial one: Phoebe’s stalker boyfriends, Malcolm (David Arquette) and Eric (Sean Penn), who were both in love with her twin sister, Ursula.

Why Phoebe's Two Ursula Stalker Boyfriends Were So Creepy In Friends

Phoebe and Malcolm sit together at Central Perk from Friends

Out of the main characters in Friends, Phoebe was the one with the most complex and tragic backstory, as her adoptive mother killed herself, her stepfather went to jail, her real father was never around, she didn’t meet her real mother until she was an adult, and she lived in the streets when she was young. It’s not surprising, then, that Phoebe repeated certain unhealthy patterns throughout Friends, and these were mostly reflected in her romantic relationships. Phoebe also didn’t have a good relationship with Ursula, so her dating two of her boyfriends, who were also quite stalkerish, was controversial and creepy.

First was Malcolm in Friends season 3, who Phoebe met at the subway station as he was following her because he mistook her for Ursula. Malcolm was obsessed with Ursula and she even had a restraining order against him, but he still stalked her all the time. Phoebe tried to help him and fell for him, but when she learned Malcolm was still stalking Ursula, she finally broke up with him. The episode was controversial as not only was it out-of-character for Phoebe to date someone as dangerous as Malcolm but it also sent a bad message to the audience. Unfortunately, the story was recycled (though with less intensity) when Phoebe met Eric in Friends season 8. Eric was Ursula’s fiancé and he met Phoebe at Monica’s Halloween party, but after she exposed Ursula’s lies, Eric broke up with her and started dating Phoebe. Eric got Phoebe’s phone number with the help of a police friend, and while that might not be as stalkerish as what Malcolm did, it isn’t a green flag either. Eric even mentioned he had trouble looking at Phoebe because she obviously reminded her of Ursula and that made him angry, but once again, Phoebe decided she could help him recover.

Phoebe’s relationship with Eric also ended because of Ursula, as Eric slept with her thinking she was Phoebe, and they broke up as their relationship was too weird. Phoebe was one of the strongest characters in Friends, so it wasn’t fair to have her belittling herself for two men that were in love (and obsessed) with her twin sister and, in Malcolm’s case, who were also dangerous. Luckily for Phoebe, she found her “lobster” when she met Mike, and she finally had the home and family she never truly had.

Next: Friends: Phoebe's Third Husband Everyone Forgets About