Messiest Celebrity Friend Breakups Ever

As social media has shown time and time again, friend breakups can be just as messy, if not messier, and traumatic as romantic breakups. In fact, we have seen messy friend breakups over and over again, not only in our own lives but also in those of some of our favorite celebrities.

From Blake Lively and Taylor Swift’s multi-year feud, which seemingly ended for good when Swift snubbed Lively at her wedding to Travis Kelce on July 3rd, to early-2000s drama we still think about today, celebrity friend breakups can be messy as heck. From Paris Hilton and Nicole Richie to Alyssa Milano and Shannen Doherty, we have a lot to go over.

Below, see which of the messiest celebrity friend breakups we still think about today.

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Demi Lovato & Selena Gomez

It all started in 2001 when Demi Lovato and Selena Gomez met while acting on Barney & Friends. After years of friendship, they launched The Demi + Selena Show on YouTube and even co-starred in Princess Protection Program together. But when Gomez and Taylor Swift got closer, tension rose. When asked about Gomez, Lovato quipped, “Ask Taylor,” back in 2010. (However, they did reunite in 2011 when Gomez supported Lovato going to rehab!)

They drifted apart for good in 2014, but have since reconnected as pals in the 2020s to support each other’s careers and milestones!

Katy Perry & Taylor Swift

Despite being pals, Katy Perry and Taylor Swift reportedly feuded over a dispute about booking backup dancers for their tours. Perry often spoke about wanting bygones to be bygones, but Swift resisted. Later, Perry released a song called “Swish Swish,” which many believed to be targeted at Swift. Along with that, Perry dated John Mayer after her. 

Per POPSUGAR, Perry publicly forgave Swift for her biting comments over the years in 2017, and by 2019, they hugged it out for the music video “You Need to Calm Down.”

However, it’s unclear if they’re pals in 2026 because Perry was snubbed from Swift’s wedding to Travis Kelce!

Blake Lively & Taylor Swift

Blake Lively and Taylor Swift were pals from 2015 to 2025, often supporting one another at movie premieres, concerts, and more. Swift is the godmother to multiple children with Ryan Reynolds, but it all came crashing down!

After Swift was drawn into the It Ends With Us drama, when her private texts to Lively were leaked, rumors of a rift between her and Lively emerged! This was seemingly confirmed when Lively didn’t congratulate Swift on her engagement to Kelce. Since then, they’ve seemingly remained out of each other’s lives, despite Swift being the godmother to her children.

Sarah Jessica Parker & Kim Cattrall

While they played BFFs Carrie and Samantha on Sex and the City, Sarah Jessica Parker and Kim Cattrall reportedly didn’t get along. According to UsWeekly, there was a falling-out during the final season because Parker was paid much more than Cattrall.

Cattrall spoke with The Daily Mail in January 2010 and said, “I think Sarah was right: People don’t want to believe that we get on. They have too much invested in the idea of two strong, successful women fighting with each other.”

However, in 2018, Cattrall took to Twitter, now known as X, to announce the sudden death of her brother, Christopher Cattrall. Parker responded, saying, “Dearest Kim, my love and condolences to you and yours and Godspeed to your beloved brother. Xx.”

Kim responded: “My Mom asked me today ‘When will that @sarahjessicaparker, that hypocrite, leave you alone?’ Your continuous reaching out is a painful reminder of how cruel you really were then and now. Let me make this VERY clear. (If I haven’t already) You are not my family. You are not my friend. So I’m writing to tell you one last time to stop exploiting our tragedy in order to restore your ‘nice girl’ persona.”

Then Kim said “No” to a third SATC film and wasn’t asked join the series’ reboot And Just Like That... 

Alyssa Milano & Shannen Doherty

Charmed co-stars Shannen Doherty and Alyssa Milano did not get along, but actually were friends for a while before everything hit the fan. In fact, Doherty was even a bridesmaid at Milano’s first wedding.

But when season two happened, it all changed!

“I think I cried every single night of season 2,” Doherty once told Entertainment Tonight, adding that their competitiveness got the best of them. 

In 2021, they seemingly reconciled, but Doherty decided to tell the world what happened when her cancer diagnosis progressed.

And in an episode of the late Doherty’s podcast Let’s Be Clear With Shannen Doherty, their third co-star, actress Holly Marie Combs, revealed what happened before Doherty left the show. “We were told [by Alyssa] that it’s her or [Shannen], and Alyssa has threatened to sue us for a hostile workplace environment,” Combs revealed.

“They forced me to go back to a show I wanted nothing to do with,” she admitted. “I ended up doing the most hours for the least pay because I just didn’t ask for raises, I didn’t want to be more taken out of the budget, I didn’t want to have no money for guest stars.”

Jordyn Woods & Kylie Jenner

Jordyn Woods and Kylie Jenner were inseparable for literal years after first being introduced by her friend-turned-boyfriend-turned-friend-again Jaden Smith back in 2012. They even lived together until 2019, when one of the biggest Kardashian controversies hit.

In 2019, Woods was caught kissing Khloé Kardashian’s then-boyfriend, Tristan Thompson; which caused a huge falling out between the two. Woods moved out of Jenner’s home and into her mom’s house. She spoke about the kiss on Red Table Talk with Jada Pinkett Smith, saying, “On the way out, he did kiss me. No passion, no nothing; on the way out, he just kissed me. Like a kiss on the lips, no tongue kiss, no making out, nothing.”

However, the two reconciled in 2023.

Winona Ryder & Gwyneth Paltrow

Back in the 90s, Winona Ryder and Gwyneth Paltrow were best friends, who were also dating best friends and actors, Matt Damon and Ben Affleck, respectively. However, their friendship seemingly ended when Paltrow allegedly stole the script for Shakespeare in Love from Ryder. Ryder was eyed for the role of Viola de Lesseps, but Paltrow snagged it and won the Oscar for Best Actress. 

When asked about the allegations, Paltrow denied them. “No, that’s an urban myth,” she said while raising her right hand during a 2015 interview with Howard Stern. “I swear to God.” 

Heidi Montag & Lauren Conrad

Despite being fast friends after meeting in 2005 at college orientation, Heidi Montag and Lauren Conrad had a well-known blowout. In 2007, at the beginning of season three of The Hills, Montag’s now-husband, Spencer Pratt, spread a sex tape rumor about Lauren. Lauren famously yelled, “You know what you did!”

Conrad didn’t return for the reboot and they’ve never reconciled.

Anderson Cooper & Kathy Griffin

Comedic tag-team Kathy Griffin and Anderson Cooper hosted the NYE festivities for 10 years, but it all changed in 2017. In 2017, Kathy took those infamous beheaded photos. She put together a photoshoot in which she featured a mask of Trump that was bloodied and made to look as if he had been beheaded. Not only did it end her career, but it ended her friendship with Cooper.

Selena Gomez & Francia Raisa

Selena Gomez and actress Francia Raisa were best pals for a while, with Raisa famously donating her kidney to Gomez in 2017. But their falling out came in 2022, when Gomez gave a Rolling Stone interview in which she said Taylor Swift was her “only friend in the industry.”

They seemingly mended their friendship in 2023, but Raisa wasn’t invited to Gomez’s wedding, fueling the feud talk even more. However, they’re seemingly on good terms in 2026.

Paris Hilton & Lindsay Lohan

Paris Hilton and Lindsay Lohan were the best of buddies in the 2000s club scene, but it all hit the fan in 2006. In 2006, Lohan started dating Hilton’s ex, Stavros Niarchos! (He and Paris Hilton dated on and off between 2005 and 2007.) And Hilton was spotted laughing at Lohan when a friend called Lohan “poor.”

Mere months later, Lohan allegedly publicly called Hilton the c-word while on camera but tried to walk it back, saying: “I never said that. I love Paris. Paris is my friend.” There was some more back and forth until 2007, when they were seen parting on the Fourth of July 2007.

They had another scuffle in 2011, but seemingly buried the hatchet for good in 2022! (They were even spotted catching up and talking about motherhood!)

Paris Hilton & Nicole Richie

Paris Hilton and Nicole Richie first met in the 1980s when they attended the Buckley School together in Los Angeles. Their friendship took our screens in 2003 when they co-starred in The Simple Life together. 

Things hit a breaking point, though, when in 2005, Hilton said she wanted her co-star to be Rod Stewart’s daughter, Kimberly Stewart. Hilton confirmed the feud later that year when she said via People: “It’s no big secret that Nicole and I are no longer friends. Nicole knows what she did, and that’s all I’m ever going to say about it.”

A couple of years later in 2007, they seemingly buried the hatchet. They’ve been pals ever since!