6 Celebrity Best Friend Duos Who Went From Inseparable To Strangers After A Dramatic Breakup

Winona and Gwyneth were best friends in the '90s and even lived together for some time. Their then-boyfriends, Matt Damon and Ben Affleck, were also inseparable, so the four actors were often seen having fun together at public events.

Their falling out is believed to have stemmed from a professional battle for a lead role: Viola de Lesseps in the 1998 film Shakespeare in Love.

Winona reportedly received the script first and was a strong contender for the role. However, once Gwyneth read it, she fell in love with the character and allegedly contacted her agent to secure an audition.

In the end, the film went on to receive ravishing reviews and won an Oscar for Best Picture. It also earned Gwyneth her first Oscar for Best Actress. 

By 2000, the actresses were no longer pictured together.

Gwyneth addressed the incident during an interview with Howard Stern in 2015, where she insisted that the script-stealing story was an "urban myth." When Howard asked if Winona believed her version, the Goop founder replied, "I haven't seen her in years."

Demi and Selena first met on the set of Barney & Friends when they were 7 years old. 

As teenagers, their friendship grew closer as they both found global fame as Disney Channel stars. In 2009, they co-starred in the 2009 Disney movie Princess Protection Program and sang a song titled One and the Same for the film.

Selena once told People magazine that she and Demi "did everything together."

Things began to change in 2010 when Selena got closer to Taylor Swift. When the Confident singer was asked by a fan how her friendship with Selena was going, she responded dramatically, "Ask Taylor." 

Selena and Taylor remain close friends. Taylor recently attended Selena’s wedding, while Demi seemingly was not invited.

In 2014, Selena appeared to confirm speculation that her friendship with Demi had become strained because she wasn’t there for her while she was struggling with an eating disorder. "She was going through things, and I was so young, and it was confusing," she said.

Though the two later praised each other for their achievements, Demi told Harper’s Bazaar in 2020 that she’s no longer friends with Selena.

It’s safe to say there’s still bad blood between Taylor and her former friend, Victoria’s Secret model Karlie Kloss.

Their friendship began in 2012. The two quickly became inseparable, going on road trips together, hanging out at the Met Gala, and even gracing the cover of Vogue together.

They also attended Coachella and at one point, one of Taylor’s representatives had to shut down a false conspiracy theory that the duo was secretly dating.

In 2016, Karlie called Taylor her “ride or die” in a birthday post, adding, “I feel blessed to count you as my friend, sister, and partner in crime.”

But over time, things turned sour. Tensions reportedly stemmed from the supermodel siding with Katy Perry during Taylor’s feud with the Firework singer, as well as Karlie appearing in photos with Scooter Braun and Kim Kardashian.

Taylor didn’t attend Karlie’s wedding in 2018. Three years later, she appears to have referenced the feud in her song It’s Time to Go, where she sings, “When the words of a sister come back in whispers/That prove she was not in fact what she seemed/Not a twin from your dreams/She's a crook who was caught.”

Kim and Paris’ off-again-on-again friendship has continued to make headlines for years. The two grew up in Los Angeles and became friends in preschool. Later on, Kim, who had a closet-organizing business, worked for the Hilton socialite.

However, after the Skims founder’s career took off following the release of her adult tape with Ray J and the reality show Keeping up With the Kardashians in 2007, the stars drifted apart.

In 2008, Paris dissed Kim during a radio interview, saying, “I would not want [Kim’s bottom] – it’s gross!” and said her derriere reminded her of “cottage cheese inside a big trash bag.”

Though the blonde superstar later apologized for her remarks, Kim confirmed in 2011 that she and Paris didn’t talk and had “grown apart.”

The pair reunited at Kris Jenner’s Christmas Eve party in 2016, where they posed for a photo together. They now appear to be on good terms, with Paris modeling for Kim’s shapewear brand in 2020 and Kim attending Paris’ wedding to Carter Reum the following year.

Anderson and Kathy were as thick as thieves for two decades and hosted the NYE festivities for 10 years.

In 2017, after Donald Trump won his first election, Kathy posted a photoshoot of herself featuring a gory mask of the president designed to look beheaded. The post cost the comedian both her job at CNN and her friendship with Anderson. 

Kathy later took down the post and admitted that she had gone too far, saying on X/Twitter, "I beg for your forgiveness.”

Anderson condemned Kathy’s behavior, saying he was “appalled” by the photoshoot, which he called “disgusting and completely inappropriate.”

That same year, he told Andy Cohen on Watch What Happens Live that he wished Kathy the best and hoped she “bounced back” after the scandal.

In 2021, during an interview with Bill Maher, Kathy clarified that she and Anderson were no longer friends. Asked if she would like to be friends with him again, she said, "Sure. Of course. I don't know that he's interested. But I mean, you know, I also don't have a need to hang out with people that maybe weren't so kosher."

Lauren and Heidi appeared together on the MTV reality show The Hills during the 2000s, which focused on the lives of young women and men in Los Angeles.

The two parted ways after Heidi was introduced to her now-husband, Spencer Pratt, in 2006.

Lauren reportedly disapproved of the relationship, warning Heidi that he was a "sucky person." Heidi even claimed that her friend threatened to get her off the show if she continued dating him.

In 2007, Heidi moved out of her shared apartment with Lauren and into one with Spencer. That same year, Spencer spread a rumor that Lauren had made an intimate tape with her ex-boyfriend, Jason Wahler.

When she met with Heidi to talk, Lauren delivered the now-iconic line, "I wanna forgive you, and I wanna forget you."

Lauren officially left The Hills after Season 5, and Kristin Cavallari replaced her as the main cast member. Heidi, along with her husband Spencer, continued on the show into Season 6.

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