Celebrities Who Had A Messy Best Friend Breakup

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Breaking up with your significant other is hard, but breaking up with a best friend who was like a soulmate is some of the worst pain imaginable.
So, let's talk about some celebrities who had to deal with a very public and very messy breakup with a close friend:
Kylie Jenner and Jordyn Woods:
Kylie and Jordyn were inseparable best friends for almost a decade. The pair met through their mutual close friend, Jaden Smith, right before high school. From living together, releasing a Kylie Cosmetics collab, Jordyn being there for Kylie during her pregnancy with Stormi, public declarations of love, and endless fashion weeks, it was clear that Kylie and Jordyn were the ultimate best friends. Well, naturally, Tristan Thompson made sure to mess that right up. Back in 2019, rumors started going around that Tristan had once again cheated on Khloé Kardashian (the mother of his children and also Kylie's sister) at a house party in LA. TMZ swiftly reported that Khloé and Tristan had broken up due to his infidelity with none other than long-time family friend Jordyn Woods. A massive fallout ensued between Jordyn and members/friends of the Kardashian family. Unfollowing each other on Instagram, shady mentions on the show, honestly, just a true dogpile.
Tristan, like always, lied and denied it by tweeting and deleting "FAKE NEWS," while Khloé's long-time best friend, Malika Haqq, commented, "STRONG FACTS" on Hollywood Unlocked's post reporting the incident. Following the reports, multiple sources confirmed that Jordyn had moved out of her home with Kylie and back in with her mother. On March 1, Jordyn took to Red Table Talk with Jada Pinkett Smith to discuss the situation, 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."
During the 16th season of Keeping Up with the Kardashians, we finally saw Kylie speak out about the incident, simply saying, "She fucked up." Kylie also voiced her allegiance to Khloé, telling her, "Just know I love you." In July 2023, Kylie and Jordyn reunited after four years of public and family feuding. Later that year, Kylie talked with Jennifer Lawrence for Interview magazine, explaining that she and Jordyn never really cut ties after the scandal. They still interacted, still hung out, and still checked in on each other regularly. Their July 2023 outing was just a moment when they realized they didn't want to hide their friendship anymore.
Paris Hilton and Nicole Richie:
It was a timeee to grow up during the Paris Hilton and Nicole Richie reign. These long-time besties grew up together and went on to star in their own reality TV show, The Simple Life, which ran from 2003 to 2007. In 2005, the pair very randomly stopped speaking and started hating each other. While the reason has never been confirmed, it was rumored their fallout was due to a horrible situation. When Paris was set to host SNL in February 2005, they, of course, celebrated with a party, and rumor has it that Nicole allegedly screened Paris's sex tape during the event. The tabloids were also going absolutely wild with speculation and rumors.
In April 2005, Paris finally spoke out about the feud, saying, "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." In November of that same year, Nicole interviewed with the Today show, telling them that she and Paris "just grew apart," and the situation "just turned into a much bigger thing than it is."Thankfully, the feud didn't last long. In October 2006, the pair were spotted loudly laughing and enjoying dinner together at a restaurant in LA. They even recreated their reconciliation for the first episode of the fifth season of The Simple Life. Thankfully, the iconic sliving duo have remained on good terms since their highly secretive, yet very public early 2000s spat.
Kim Kardashian and Larsa Pippen:
Kim and Larsa have been friends since 2010. They met and grew close during the filming of Kourtney and Kim Take Miami, and Larsa frequently guest-starred on the show. Eventually, Larsa became a regular member of the Kardashian clan, even being there for many of Kim's milestones, like marriage and motherhood. However, things went completely sour in 2020.After a decade of growing close, taking tons of trips together, celebrating birthdays, and even Larsa having her hand in trying to set Kim and Kanye West up back in 2010, things went totally left. In July 2020, reports started that Kim and Larsa had fallen out after Kim never appeared at Larsa's 46th birthday party. Shortly after, fans realized the big three, Kim, Kourtney, and Khloé, had all unfollowed Larsa on Instagram. By the end of the month, Larsa spoke out on Twitter about the "rumors," saying, "I woke up this morning blessed and see that everybody is focused on who I am following and who I am not following on social media. I am focused on my children, my new fitness brand, Larsapippenfitness, and my relationships in real life."
By November 2020, Larsa was singing a completely different tune. Appearing for an interview on the Hollywood Raw podcast, Larsa finally spoke her truth about the falling out with Kim. Larsa admitted that she and Kim now have a "different kind of relationship" but then went on to insinuate that Kanye caused the rift in their relationship: "I just feel like Kanye was in a place where he, you know, he really didn't trust anyone with Kim." She continued, saying, "If your husband feels threatened by my relationship with you, then I don't want to be that person." After the interview was released, sources told E! News that the Kardashian family didn't trust Larsa's intentions and believed she "is toxic energy."Larsa would publicly discuss her relationship with Kim via multiple media outlets over the next few years. In 2022, she spoke to Access Hollywood, telling them, "We're cool, we're friends. There's no beef, there's no bad situation. If I see her out, obviously, we're going to speak; it's not what people want it to be." Kim never outwardly spoke out about the feud.
Demi Lovato and Selena Gomez:
Demi and Selena first met in 2001 on the set of Barney & Friends when they were just 7 years old. Their friendship grew closer in their teens when they both moved on to their careers on Disney Channel. The pair were so iconically close that Disney had to capitalize on it and had them star side-by-side in the 2009 movie Princess Protection Program. That same year, they did a spread for People, where Selena said the pair "do everything together."
As they got older, things started to take a turn. In 2010, as Selena's friendship with Taylor Swift grew, it was clear that Demi and Selena's relationship was suffering because of it. When Demi was asked by a fan how her friendship with Selena was going, she responded, "Ask Taylor." That same year, she spoke again about their friendship status: "We're both busy, and I wish the best for her. True friends don't let their friends or family be mean to you. If you can't trust somebody, you can't be friends with them."Sources claimed that Demi's problem with Selena was that she felt like their friendship wasn't reciprocated and that Selena wasn't there for her, especially while Demi was suffering from her eating disorder and self-harm issues. Selena confirmed this when she spoke to Seventeen in 2014: "She was going through things, and I was so young, and it was confusing. I processed it saying, 'OK, I don't understand what she's going through, so I'm just going to do this.' I don't think it was fair, and I'm so happy that I have her back in my life now."
The two spent the better part of a decade following and unfollowing each other on social media, randomly congratulating or praising each other for accomplishments, and speaking on their relationship to various sources. In 2018, following her drug overdose, Demi unfollowed Selena and others on Instagram to "focus on herself" and "avoid any difficult relationships." In 2020, Selena randomly praised Demi on Instagram after her comeback Grammy performance. Later, Demi spoke to Harper's Bazaar and had this to say about the message, "When you grow up with somebody, you're always going to have love for them. But I'm not friends with her, so it felt ... I will always have love for her, and I wish everybody nothing but the best."
Winona Ryder and Gwyneth Paltrow:
Back in the 90s, these two lived lives that are only written about in fan-fiction. They were both two of the hottest actors at the time, best friends, and dating two of the hottest male actors at the time — Matt Damon and Ben Affleck, who were ALSO best friends. How iconic, right? The girls (and oftentimes their partners) were spotted out together at glamorous events and having the time of their lives. Gwyneth and Winona were inseparable; they even lived together for a period of time during the '90s.
Well, not all friendships are lifetime ones. Allegedly believed to be around late 1998, Winona had a script for the movie Shakespeare in Love, in which she was being eyed to play the role of Viola de Lesseps. Rumor has it that once Gwyneth saw the script, she immediately fell in love with the lead role and contacted her agent to set up an audition, and she eventually snagged it. Not only did she get the role, but the movie won an Oscar for Best Picture, and Gwyneth won her first Oscar for Best Actress. By 2000, the ex-besties were no longer seen together, nor were they friends, and everyone knew it. While neither was too keen to speak about the fallout, Gwyneth came to her own defense in 2015 during an interview with Howard Stern. In the interview, she was flat-out asked about the incident and had this to say: "No, that's an urban myth,' Gwyneth said while raising her right hand, 'I swear to God.' When Howard asked if Winona actually believed that, Gwyneth confessed, "I haven't seen her in years."
James Franco and Seth Rogen:
The once-dynamic acting duo met in 1999 on the set of the series Freaks and Geeks. At the time, Seth and James were 17 and 21, and they became very close friends and "bonded for life." Franco even told the New York Times in 2014 that he's written poems about the power of his friendship with Seth. I mean, the pair collaborated for so many films and even a few TV shows; there was a point in time when they almost seemed like a package deal.
However, personal indiscretions seemed to put an end to this longtime professional and personal relationship. Beginning in 2014, James would go on to be accused of and admit to a slate of alarming things. In 2014, the then-35-year-old admitted to messaging and attempting to meet up with a 17-year-old girl. He even had this to say during an interview on Live with Kelly and Michael, "I guess I'm, you know, embarrassed, and I guess I'm just a model of how social media is tricky." He essentially chalked the whole thing up to "bad judgment." In 2018, five women James taught in a master class he called "Sex Scenes" at his acting school Studio 4 spoke out to the LA Times, mainly about the horrible sexual exploitation and uncomfortable situations they allegedly faced at the hands of Franco. At the time of the 2018 allegations, Seth stated that he would continue working with James, but his views have significantly changed since then.
By 2019, James had found himself accused of another crime. An additional student at his Studio 4 acting school alleged that he and his business partners engaged in "widespread inappropriate and sexually charged behavior toward female students." After many allegations, confessions, and horrid truths, Seth finally spoke out about his and James's relationship again in 2021. He told Britain's Sunday Times that the allegations "changed many things in our relationship and our dynamic." Then, he cleared up their working relationship, saying, "I also look back to that interview in 2018 where I comment that I would keep working with James, and the truth is that I have not and I do not plan to right now."
Lauren Conrad and Heidi Montag:
Tons of millennials will remember being glued to their TVs to soak in the drama of The Hills during the early 2000s, especially when the drama with best friends Heidi and Lauren broke out. When Heidi was introduced to her now-husband Spencer Pratt in 2006 by fellow cast mates Kristin Cavallari and Brody Jenner, it was essentially the beginning of the end of LC and Heidi's relationship. When Heidi and Spencer started dating, LC repeatedly tried to warn her about him. She would say things like he's a "sucky person," and according to Heidi, even once told her, "I don't like Spencer. If you keep dating him, then you're off the show." After many arguments, Heidi eventually chose Spencer, and in 2007, she moved out of her shared apartment with Lauren and into one with him. Here's where things go entirely left: That same year, Spencer spread a nasty rumor that LC and her ex-boyfriend Jason Wahler had made a sex tape. When LC ran into Heidi at a birthday party on the show, she told Heidi, "You're a bad person. I feel bad for you. You know what you did. You're a sad, pathetic person."
After the incident, Heidi attempted to apologize and deny any knowledge of Spencer's wrongdoing. She met up with Lauren at her house for a talk, and Lauren gave us the iconic friendship ending line, "I wanna forgive you, and I wanna forget you."Two years later, LC attended the couple's 2009 wedding to shoot her final scenes for the show but left early to attend another event. Spencer, LC, and Heidi went back and forth for years over the situation. After eons of both Heidi and Spencer vehemently denying any involvement or knowledge, Spencer finally admitted he was the one who spread the rumor in 2015 during an interview with Complex. Even after admitting to doing such a horrible thing they lied about and covered up for years, the pair still proceeded to throw immense shade at LC.
Anderson Cooper and Kathy Griffin:
Before we had the hilarious and drunken antics on CNN New Year's Eve Live of Andy Cohen and Anderson Cooper, former close friends for two decades Kathy Griffin and Anderson Cooper hosted the NYE festivities for 10 years. It wasn't until 2017 that we saw a horrible fallout from some of Kathy's actions. In 2017, amid most people (rightfully) losing their minds over then-POTUS Donald Trump, Kathy put together a nonsensical photoshoot in which she featured a mask of Trump that was bloodied and made to look as if he had been beheaded. The picture immediately received backlash after being posted on the internet. Kathy was threatened with being charged with conspiracy to assassinate the president, put on the no-fly list, subject to intense searches at airports, and ultimately lost her job with CNN. Not to mention, it was the end of her 20-year friendship with Anderson Cooper.
Immediately after the photo surfaced, Anderson took to Twitter to condemn the whole thing, saying, "For the record, I am appalled by the photo shoot Kathy Griffin took part in. It is clearly disgusting and completely inappropriate." While Kathy was telling the media how hurt she was by Anderson, that same year, Anderson went on Watch What Happens Live with host, best friend, and Kathy's new replacement, Andy Cohen. During the interview, and like others before it, he claimed he and Kathy were okay, saying, "Yeah, we're still friends. Look, I said what I said about… I didn't think what she said was appropriate." He continued, "I wish her the best, and I hope she bounces back and is back on the road. She's incredibly funny, and a lot of people love her, and I think she'll bounce back from this."
Well, in 2019 during an interview, Kathy told People Now that making amends with Anderson probably wouldn't happen because she "doesn't think he's that kind of guy." In 2021, during an interview with Bill Maher, Kathy clarified that she and Anderson were not friends and threw quite a bit of shade (which isn't the first time). When Bill asked if Kathy would ever get over it and make amends with him, she replied, "Sure. Of course. I don't know that he's interested. But I mean, you know, I also don't have, like, a need to, like, hang out with people that maybe weren't so kosher."
Are there any other famous BFF breakups that you'll never forget? Let me know in the comments!