Keeping Up With the Kardashians is a little reality show on E! that you may or may not have heard of. Alright, who are we kidding, you’d have to be living under a rock not to know who the Kardashian-Jenner’s are. For over ten years, we have followed the ins-and-outs of their lives, witnessing everything from 72-day marriages to the birth of their children.
And in a way, we watched them all grow up. Kendall and Kylie were just kids when the show started. Now they are powerhouse bosses themselves. (Hello billion-dollar empire.) Along with conquering the television world, the sisters (and mom-ager Kris Jenner) have become national icons.
Over the years, we not only watched the trials and tribulations of their love lives but their problems with friends as well. Being a member of the Kardashian-Jenner inner circle is not an easy place to get to. But once you do, you’ll be treated to fabulous products, parties, and vacations beyond your wildest dreams. (Still waiting for our invite to Kylie’s next European Birthday Trip, btw.)
If you cross the family, though, the fallout will be nothing short of nuclear. The Kardashians and Jenners are famously private. So if you break their trust, you’re out the door. Over the years, several of the former Kardashian-Jenner friends betrayed the family and hit the curb.
Let’s take a look at all the former Kardashian-Jenner friends who turned into nemesis, not just frenemies.
Stephanie Shepard
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Can you ever really be friends with your boss?
Stephanie Shepard started out as Kim Kardashian’s assistant in 2013. And over time, the two formed a pretty close friendship; they seemed to be together ALL the time.
It’s understandable that they formed a bond.
Things were going so well that Kim even gave Shepard a bigger role in her business. But things started to get weird between the two not long after, going from bad to worse.
According to multiple reports, Kim made the decision to fire her assistant in November 2017.
And the move came not long after Shephard received a promotion. Apparently, Kim felt the position was a bad fit when Shepard revealed to Kourtney that she was feeling “unfulfilled, job-wise.” Regardless of whether the woman meant her words or not, Kim didn’t take it well. She found the entire situation inappropriate.
The second oldest Kardashian also allegedly hated that Shepard and Kourtney became so close.
However, after the news outlets picked up the story of the feud, the Shephard and Kim made a video, claiming there really wasn’t any bad blood between them. The video may have been forced, but we’ll never know exactly what happened.
All we know is Shephard been seen around much since.
Brittny Gastineau
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Next time, just don’t say anything.
We’ve all had that one friend who dated someone we just couldn’t stand. And what’s the best thing to do about it? It’s debatable. But many people just bite their tongue and wait for the relationship to end naturally, as they often do.
What happens when your friend goes on to marry the person who isn’t right for them, though?
Heads may roll. Just ask Brittny Gastineau. She tried her best to persuade Kim to make a different decision. But apparently, her advice wasn’t received well. Before Kim married Kanye and became half of one of the world’s biggest power couples, she was engaged to NBA play Kris Humphries.
We all remember that.
The marriage famously lasted less than three months. And everyone was like, “Who let Kim do such a thing?” Well, as it turns out, Kim’s best friend tried to halt the entire fiasco. Gastineau allegedly confronted Kim and said she was making a huge mistake.
Kim didn’t take it well, though.
According to friends, when Gastineau confronted Kim saying she was “concerned about [the marriage] decision and wanted [things] to slow down,” Kim flipped out. The two women purportedly got into a huge fight. And although the disgraced pal was invited to the wedding, they barely spoke after. Once the marriage ended, however, Kim realized the warning came from a good place. It seems like they finally buried the hatchet.
Joyce Bonelli
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The face of the family.
Joyce Bonelli is a celebrity makeup artist who made a name for herself by being the family favorite of literally every Kardashian and Jenner sister. Bonelli spent over ten years with the family, applying glitter, perfecting the perfect liquid line, and helping Kylie achieve her over-lined lip look.
Then there was a secret falling out.
According to reports, the mogul family fired Bonelli and completely froze her. They seemingly don’t “speak to her anymore.” But, Bonelli said she was never fired at all. To her, the whole ordeal was simply a tiff between friends.
What’s even weirder is that she posted about the situation on social media often.
The artist claimed to communicate with the sister every day. Tellingly, the Kardashians remained silent.
So, what happened?
Apparently, Bonelli planned to release her own makeup line called Joyce Bonelli Cosmétiques. And that decision created a fight with the family. We guess her collection directly competed with Kylie’s cosmetics company and Kim’s KKW collection as well. Sounds like too many cooks in the makeup kitchen to us.
Jordyn Woods
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Ah, the friendship to end all friendships.
Perhaps the biggest BFF scandal to rock the Kardashian-Jenner clan occurred with Jordyn Woods in 2019. In case you need a quick refresher, let’s backtrack for a second. Kylie and Jordyn were super close for years, since their preteen days. To say the two women were inseparable was an understatement. They lived together; they traveled together.
Woods even helped Kylie look after her newborn, Stormi.
And she wasn’t just close with Kylie. While Woods was no doubt Kylie’s best friend, she also hung out with the entire Kardashian-Jenner family. They invited her on trips and included her in everything. So, when news broke suggesting that something inappropriate happened between Jordyn and Khloe’s former BF, Tristan Thompson, all hell broke loose.
The family felt devastated.
Reportedly, Woods downplayed the whole situation. And it wasn’t until several friends came to Khloe with details of the alleged night that she truly believed what she heard. What followed was a she said-she said about whether or not Woods apologized and what really happened. Woods also famously went on Jada Pinkett Smith’s Red Table Talk to give her side of the story.
Then, they cut her off.
Shortly after the situation went public, Woods moved out of Kylie’s house and went back home. Almost the entire Kardashian-Jenner family unfollowed her on social media. And Kylie was caught in the middle; she lost her closest friend.
The youngest Jenner sister continued to Woods on social media for a bit.
And apparently they remained slightly in contact, but the damage was done. Whether or not they will ever forgive Woods is debatable. But her friendship with Kylie will certainly never be the same.
Ciara
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Yes, they really used to be friends.
We love the pop star who topped the charts in the 2000s with hits like “1,2, Step” and “Goodies.” And when she wasn’t busting moves on the dance floor, Cierra hung out with bestie Kim Kardashian. They chilled all the time.
And we do mean ALL the time; there’s plenty of paparazzi pics to prove it.
So, we’re not 100% sure what started the tiff. Ciara started to focus on faith and family. And apparently, she didn’t think Kim fit into her new lifestyle. The two haven’t hung out in years. While Kim remained tight-lipped about the falling out, Khloe got involved in 2016.
Maybe this time, though, Khloe should have kept her head down.
Right before Ciara was set to marry her current husband, Russell Wilson, Khloe called them out for waiting until marriage. Needless to say, Ciara didn’t take the jab well.
She probably felt like her intimate business didn’t involve the Kardashians
A friend close of the singer said, “[Ciara’s] really too busy jet-setting and exploring the world with her man. Yes, her man! She has one!” Yikes.
The Jenner Brothers
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Friends or family?
Remember when the Kardashians and Jenners were one happy family? Well, a sort of happy family. There were a couple of seasons on Keeping Up With the Kardashians when Brody and Brandon Jenner made appearances.
It was a blended family at its peak.
In fact, the family members all appeared to spend much more time together despite their tension with Kris. The Jenner boys have a different mom, if you were wondering.
Now, they barely seem to speak.
There was a bit of drama when Kim didn’t let Brody bring a date to her wedding with Kanye. Plus, following Caitlin Jenner’s transition and Kris’s divorce from the former Olympic athlete, the families’ communication seemingly got even more infrequent.
This Kardashian-Jenner friendship feud seems even worse because they’re all related.
Apparently, Brody didn’t even bother inviting Kendall or Kylie to his wedding a few years later. While the clans may have never been best friends, this is one intense fallout nonetheless. We hope they work it out for family’s sake.
Justine Skye
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A fight over an ex never goes well.
Justine Skye and Kylie Jenner used to be the best of friends back in 2015. The singer/model always spent time with Kendall and Kylie at festivals, parties, and other events. Skye also popped up in one of Kylie’s lip kit promotional shoots. However, the friendship seemed to go downhill fast when Travis Scott entered the picture.
Both women allegedly dated the rapper.
Scott and Kylie started dating in around 2017, and they raise daughter Stormi together. However, before dating Kylie, Scott was linked to Skye in 2015 and 2016. At the time, it wasn’t an issue since Kylie was still in a long term relationship with Tyga.
But then things got complicated.
After Kylie and Tyga broke up in 2017, news outlets reported that the young beauty mogul was dating the Astroworld rapper. Skye suggests that there’s no real drama between her and Kylie, but they definitely don’t interact like they used to. We love Kylie, dating a friend’s ex just doesn’t seem right, though.
Adrienne Bailon
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She’s married and employed as a successful daytime TV host now.
But back when Keeping Up With the Kardashians just started out, Adrienne Bailon was the former cheetah girl dating Rob. The Real host was even a huge part of the first few seasons of the show and became super close with all of the sisters. She and Rob lived together and spent holidays at Kris’s home.
But Rob cheated on her.
Bailon took the breakup hard, understandably. And while the girls were open about how much he messed up, the friendship definitely changed a lot. The Kardashians and Bailon remained close for a while; she got an invitation to Khloe and Lamar Odom’s wedding.
All hope isn’t lost, though.
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Bailon still seems to keep in touch with Kourtney. So maybe reunions with the other Kardashians are in the near future.
Monica Rose
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The most stylish breakup of all.
The Kardashians and Jenners are known for their amazing and trendsetting style. Yes, we have Kim to blame (or thank) for the bike shorts. A huge part of the family’s fashion looks came from Monica Rose.
She worked as a stylist for the family for quite some time.
Seemingly out of the blue, though, the family fired Rose. However, she continues to pull looks for several other of their famous friends including Chrissy Teigen and Cara Delevingne.
So, what happened?
Kim went on Watch What Happens Live with Andy Cohen and spilled some of the tea regarding the drama. In response to a question about whether the split was related to Kanye West changing up her style, Kim said, “So I think people think that’s the reason, and for me, maybe that is the reason. I needed a new vibe.”
Things, however, might not be so clear cut when it comes to the other sisters.
Kim hinted that they might have their own reasons for parting ways with Rose. And one thing is for sure, when one sister has a falling out with a friend, the family always presents a united front.
Blac Chyna
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Chyna was friends with the family longer than people might realize.
While the drama between Rob Kardashian and Blac Chyna is hardly a secret, few people know that social media personality has a long-standing history with the family. She started hanging out with them, particularly Kim, in 2013.
And her original drama was with none other than Kylie Jenner, the youngest of the famous family.
When Chyna found out that Kylie was dating her ex, rapper Tyga, she went after the younger woman on social media. Chyna felt betrayed. They eventually made up, but the situation got heated again when Chyna started dating Rob.
The only male Kardashian entered into a whirlwind romance with the Instagram model.
The couple even had a daughter, Dream, together and seemed content. Things fell apart yet again. Rob and Chyna had a turbulent relationship, and both of them resorted to name-calling and bullying on social media.
Think the situation couldn’t get worse?
Well, it did. There was also fallout from alleged cheating, a sex tape, and child support. The sisters tried to be friends with Chyna while she was with Rob, but when things soured, the family cut her out. Reportedly, they never wanted Chyna to be with Rob in the first place.
Courtenay Semel
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Who?
There are a few friends of the famous family that have been around since the beginning, pre-reality show days. Courtenay Semel has been friends with Kim since childhood. The two used to be inseparable. Somehow, though, the relationship fractured.
Semel started partying.
And allegedly, she was involved in a love triangle with Lindsay Lohan and Samantha Ronson. Talk about a TBT.
Regardless of what happened, the woman is definitely on the outs with the Kardashians and Jenners now.
How do we know? Well, none of them follow her on Instagram. And that is one of the golden rules of friendship in the modern world. There is also the rumor that Semel wrote an anonymous article for Refinery29 about her money.
Seems bizarre.
A fallout between old friends is never an easy pill to swallow, but we hope Semel has moved on and is happy.
Did we miss any of the Kardashian and Jenner old friends?
These famous sisters don’t just have their fair share of ex-BFFs. They also have an impressive collection of ex-lovers.
Let’s take Kourtney, for example.
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The eldest Kardashian has been in a steady relationship for most of her television career, but a hot fling suggests this hot mom is ready for some fun. Kourt and Scott Disick were already dating when the first episode of Keeping Up With The Kardashians aired.
The couple very publicly aired their dirty laundry but looked like they were going to survive despite it all.
But seemingly, the duo split for good in 2015. Scott is still an integral part of the family and the show, though. And they both co-parent excellently.
Following her breakup with Scott, Kourtney began dating a younger boxer and model, Younes Bendjima.
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The French hunk was spotted on various yachts with the oldest Kardashian sister. And the two seemed to have a lot of fun until Younes let all his jealousy get in the way.
Bendjim commented on a bikini shot of Kourtney, asking “That’s what you need to show to get likes?” And the relationship fizzled from there. We think she’s better off!
