The 55 most dramatic and jaw-dropping moments on 'Keeping Up With the Kardashians'

Nicole Pomarico,Claudia Willen
·25 min read
keeping up with the kardashians
"Keeping Up With the Kardashians" will end in 2021. Brian Bowen Smith/E!
  • E!'s hit reality show "Keeping Up With the Kardashians" is ending after 14 years and 20 seasons, Kim Kardashian West announced on September 8. 

  • The final season will air in early 2021. 

  • "KUWTK" has followed the Kardashian-Jenner family through ups-and-downs, chronicling countless shocking moments.

  • Visit Insider's homepage for more stories.

Now that Kim Kardashian West has announced that E! will air the final season of "Keeping Up With the Kardashians" in early 2021, it's time to reminisce on some of the show's most over-the-top moments. 

Throughout the 20 seasons of "KUWTK," the famous family has aired out all their dirty laundry — the good, the bad, and the utterly jaw-dropping.

From Kim's robbery to Caitlyn Jenner's transition, the Kardashian-Jenner family has given the world an inside look at their lives, and some moments from the series have been so dramatic they're impossible to forget.

Read on for the most shocking and heartbreaking moments from "KUWTK."

Kim lost Kourtney Kardashian's nude photos.

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"This is a case for the FBI." Kevork Djansezian/Getty Images

During the first season of "KUWTK," Kourtney's nude photos leaked after Kim stole them and put them in her purse as a prank.

Kim's purse was stolen, and when she realized that meant her pictures could leak, she panicked. The family called in the FBI for help since Kourtney was underage when the photos were taken, and in the end, they never surfaced.

Khloe Kardashian was arrested on charges of driving under the influence.

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Khloe Kardashian appears on "KUWTK." Amy Graves / Contributor/Getty Images

Khloe supposedly reenacted her arrest outside of a club in 2007 for the "KUWTK" cameras, according to a book called "Kardashian Dynasty."

The show also followed Khloe the morning she went to jail after violating probation, including the famous scene when Kris Jenner told Kim to stop taking selfies in the car because her "sister's going to jail."

The sisters got into a spat early on, and Kim hit Khloe with her purse.

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Khloe Kardashian and Kim Kardashian West on "KUWTK." E!

On what is remembered as one of the most iconic episodes in the second season of the show, Kim hit Khloe with her purse and said, "Don't be f---ing rude," after an argument involving a Bentley.

Kim posed for Playboy for the first time.

Kris Jenner supported Kim Kardashian West during the shoot. E!

In the first season of "KUWTK," Kim posed for Playboy for the first time and brought mom Kris along with her for support. At the time, her decision to pose for the magazine came as a surprise.

Kim, Kourtney, and Khloe snuck off to a swimwear shoot.

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They tried to keep the shoot a secret from Caitlyn Jenner. E!

Despite the fact that Caitlyn Jenner voiced her concerns about the older sisters participating, Kim, Kourtney, and Khloe snuck off to Mexico to model for Ashley Paige swimwear. They had a blast, but their secret didn't stay a secret for long.

Khloe unexpectedly married Lamar Odom.

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Khloe and Lamar's wedding was shown on a special episode of "KUWTK." E!

In 2009, Khloe married Lamar just one month after they started dating.

At the time, Kardashian's family was shocked to find out she was taking such a huge step so early on in their relationship, but they quickly pulled it together for her big day.

Later, the newlyweds scored their own spin-off reality show on E!, "Khloe and Lamar."

Khloe made a nude video for Lamar.

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The video ended up being pretty public. E!

When Khloe and Lamar were still married, Khloe made a surprise sexy video for him but was embarrassed when he ended up watching it with her brother, Rob Kardashian.

Khloe and Lamar decided to get divorced.

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Kardashian filed for divorce twice. Jamie McCarthy/Getty Images for Yeezy Season 3

Five years after the unexpected wedding, Khloe decided to file for divorce from Lamar in 2014.

Khloe discussed the divorce on the show numerous times. Ultimately, Khloe ended up calling off their divorce a year later after Lamar's overdose but filed again in 2016. Their divorce was finalized later that year.

Scott Disick's wild night in Las Vegas raised a few eyebrows.

Scott Disick stuffed a bill in the waiter's mouth on an episode of "KUWTK." E!

In a 2010 episode, the family was in Las Vegas for Kim's birthday when Disick got so drunk that Kris told the waiter to stop serving him drinks.

Disick got mad and stuffed a $100 bill in a waiter's mouth, embarrassing Kourtney.

Kris met up with her ex-boyfriend Todd Waterman.

Kris Jenner came clean about meeting Todd Waterman. E!

Things got tense on the show when Kris agreed to see her ex-boyfriend Todd Waterman while she was still married to Caitlyn.

Kris' kids were also upset with her because Todd Waterman was the person with whom she cheated on Robert Kardashian.

Kim had a meltdown when she lost her diamond earring.

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Kim Kardashian West lost her diamond earring. E!

After Kris Humphries threw her into the ocean in Bora Bora, Kim started sobbing after losing a $75,000 diamond earring.

This gave way to one of the most iconic Kardashian moments when Kourtney simply said in response, "Kim, there's people that are dying."

Kylie Jenner found the earring shortly after.

Humphries proposed to Kim.

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Kris Humphries popped the question on film. E!

Many were shocked when Humphries popped the question on an episode of "KUWTK" just seven months after meeting Kim.

The show followed Humphries choosing the ring and planning the proposal with Kris and Kim's friend Jonathan Cheban.

And then Kris and Kim got divorced after 72 days of marriage.

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Viewers watched Kim struggle with her marriage on "KUWTK." Jamie McCarthy/Getty Images

What was more shocking than Humphries' proposal? The fact that their marriage ended so quickly.

Although the episode aired long after people knew that the couple had called things off (after 72 days), Kim was devastated when she talked about going through with the wedding so she wouldn't disappoint people on "Kim and Kourtney Take New York."

Kim and Kanye West's relationship began.

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Kim Kardashian and Kanye West started out as friends. Jamie McCarthy/Getty Images

Not long after ending her marriage to Humphries, Kim and Kanye started dating and Kim was very vague about their relationship on the show.

At first, they didn't want to admit they were together and kept insisting they were just friends, but eventually, they couldn't hold out any longer, especially when the family noticed that Kim was wearing "KW" earrings.

Kourtney Kardashian pulled Mason out during delivery.

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Kourtney Kardashian did this with Mason and Penelope. E!

We witnessed Kourtney's entire journey during her pregnancy with Mason, including his birth.

Kourtney surprised viewers and her entire family by finishing her delivery by pulling Mason out.

This wasn't her last time doing it either — we also saw that when Kourtney was giving birth to Penelope.

Kim stole Kourtney's breast milk.

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Kim Kardashian West and Kourtney Kardashian appear on "KUWTK." E!

When the two were living together in Miami, Kim's psoriasis got much worse and she read online that breast milk helped with the red spots.

What started as Kim taking a bit of Kourtney's breast milk that was in the fridge, turned into much more when Kim thought that it was working and needed more.

Kourtney finally got wind of the fact that Kim was taking her breast milk and decided to directly squirt her breast milk onto Kim's psoriasis. 

Kris got a pet monkey.

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Kris Jenner briefly had a monkey named Suzie. E!

When Kourtney, Kim, and Khloe noticed that their mom had babies on the brain, they tried to mitigate the problem by getting Kris her very own pet monkey.

Turns out, the monkey was a little bit too much for Kris to handle, so Suzie went back home.

Kris and Caitlyn decided to get a divorce.

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Kris and Caitlyn Jenner had been married for 25 years. John Sciulli/Getty Images

Although they announced their separation in an earlier episode, Caitlyn and Kris decided to get divorced.

In the show's 10th season, Kris and Caitlyn's divorce put a huge strain on the family, especially for Kendall and Kylie, as they learned to navigate life with their parents living apart.

Disick angered Kourtney during a trip to Las Vegas.

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Scott Disick at a Las Vegas club appearance. Bryan Steffy / Stringer/Getty Images

When Disick told Kourtney that he was headed to Las Vegas, the family hoped he would be on his best behavior.

Although he was there for a gig he booked for Kris, he ended up getting belligerently drunk, angering Kourtney, who was pregnant with their third child, Reign, at the time.

Kourtney and Disick decided to call it quits for good.

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Kardashian and Disick broke up in 2015. AP

Although Kourtney and Disick's relationship was a rollercoaster throughout the course of their time on "KUWTK," they ended things for good in 2015 after Disick was caught getting close to another woman while on a trip in Monte Carlo.

"He's not being a good partner to me," Kourtney said on the show. "I could never rely on him, depend on him for one single thing and I don't want to show my kids that that's OK."

Disick went to rehab.

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Disick went to rehab after Kourtney broke up with him for good. E!

In 2016, it was revealed on "KUWTK" that Disick had checked into rehab. Khloe said she hoped that Disick would stick with it, and it led to many emotional scenes for the family.

Kim gave birth early to her oldest child, North West, due to complications.

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Kim Kardashian West getting ready to give birth to North West on "KUWTK." E!

Kim gave birth to North five weeks early after finding out that her preeclampsia was causing her liver to fail.

This wasn't the only time that Kim struggled with pregnancy. Suffering from placenta accreta led her to use a surrogate for her younger children, Chicago and Psalm. 

Rob lashed out at his family.

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He felt the family didn't believe that he was actually in trouble. E!

In season six, Rob lashed out at his family when he thought they weren't taking him seriously and didn't come to pick him up when he was stranded without a ride, which led to a screaming match between him, Kris, and his older sisters.

"You don't even pay attention to half the things I say," he said before storming out.

Disick lost both of his parents in a short amount of time.

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Scott Disick's parents died within three months of each other. Alexandra Wyman/Invision for Asphalt/AP Images

Disick's father Jeff died just three months after his mom Bonnie died, and the loss deeply affected Disick.

Caitlyn announced she was transitioning.

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Caitlyn Jenner on "KUWTK." E!

In a "KUWTK" special, Caitlyn Jenner revealed that she was a transgender woman publicly for the first time and announced that she was beginning her transition.

In the special, Kris and their children spoke to the camera in interviews about what her transition has been like for them behind closed doors.

The family staged an intervention for Rob.

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Rob Kardashian has discussed his depression on the show. E!

Before Rob stopped appearing on "KUWTK," the family grappled with his depression.

In a 2015 episode, the Kardashians confronted him about his depression and health, staging an intervention for him. At the time, Kris even said that she was worried he might die.

Kim was robbed at gunpoint in Paris.

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Kim explained her experience to Khloe on "KUWTK." E!

In October 2017, Kim Kardashian was robbed at gunpoint in her hotel room during a trip to France for Paris Fashion Week.

When the next season of "KUWTK" aired, Kim relived that night to explain to the cameras (and her sisters) exactly what she was feeling in that moment.  

"They had the gun up to me and I just knew that was the moment they are just totally going to shoot me in the head," Kim said in the episode. "I just prayed Kourtney was going to have a normal life after she sees my dead body on the bed."

Rob refused to attend Kim and Kayne's wedding.

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Kim Kardashian West got married to Kanye West. E!

When the family flew first to Paris and then Italy to see Kim and Kanye tie the knot, Rob flew to Paris but ultimately decided to turn around and go back home because he didn't feel like being in the public eye at the time.

Kim was upset when she received the email sharing the news with her, but proceeded with her wedding as planned.

Caitlyn's memoir caused a rift in the family.

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Caitlyn's memoir was the last strike for Kris Jenner. Kevin Winter/Getty Images

Caitlyn's memoir, "The Secrets Of My Life," caused major drama in the family due to her portrayal of her life and marriage to Kris.

The Kardashians were quick to defend their mom. They've since talked about how their relationship hasn't been the same and Caitlyn no longer makes appearances on the show.

Khloe and Caitlyn's feud caused a permanent rift.

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Khloe said she no longer speaks to Caitlyn. Jamie McCarthy/Getty Images

After hearing what Caitlyn wrote about Kris in her book, Khloe stopped responding to Caitlyn's text messages, despite the fact that they used to be very close when she was still married to Kris.

At the time, Khloe declared that she no longer had a relationship with Caitlyn.

Kendall opened up about her anxiety.

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Kendall has been open about her mental health on the show. E!

While Kendall was preparing to travel outside the country for work, she had a panic attack and Kris explained on the show that she needed to fly to where Kendall was to help her get on her next flight. 

Since then, she's been open about her anxiety on the show, especially when it comes to flying.

Kim went off about Taylor Swift over the singer's feud with Kanye.

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Taylor Swift, Kanye West, and Kim Kardashian West. Getty Images Entertainment/Larry Busacca

Just before Kim released videos of Swift's phone call with Kanye on her Snapchat account, she and Khloe didn't hold back about their feelings about the pop star, and shared their side of the story on an episode of "KUWTK." 

Rob and Blac Chyna got engaged.

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The two had a very on-again-off-again relationship. AP

Rob had been laying low for a couple of years, so everyone was shocked when they found out that he was engaged to Blac Chyna — especially since his sisters found out through news stories online, and not from their brother himself.

Chyna announced she was expecting a baby.

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Blac Chyna's Instagram baby announcement. Instagram/BlacChyna

In that same episode, Rob told his sisters that Chyna was pregnant, and the news seemingly blindsided them.

Even though Rob and Chyna are no longer together, they continue to co-parent their daughter Dream together.

Odom nearly died after a drug overdose.

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Lamar Odom on "KUWTK." E!

When Lamar Odom overdosed at a Nevada brothel in 2015, Khloe originally received a text saying that he'd died, only to find out later that he was actually in a coma.

Filming of the show shut down for a couple of days and Khloe didn't leave Odom's side the entire time he was in the hospital.

Filming resumed as Odom was being transported to a hospital in LA and Khloe was able to come home.

The only footage inside the hospital was from a camera phone of West playing Odom some of his new music, despite the reports that the "KUWTK" cameras were set up in the hospital.

Kris had an allergic reaction on vacation.

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The family continued to enjoy their vacation. E!

While the family was relaxing in the Dominican Republic together, Kris' lip swelled up and her family was less than sympathetic to her.

It turned out that her lip was a reaction to something she'd eaten while on vacation.

Kylie revealed she used lip fillers.

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There was lots of speculation before Kylie admitted it. E!

After months of speculation that Kylie had a cosmetic procedure to enhance her lips, she admitted on "KUWTK" that she actually had gotten lip fillers because she felt so self-conscious about the size of her lips.

Kim found a woman in Disick's hotel room.

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Kim took matters into her own hands. E!

When Disick accompanied Kim on a work trip to Dubai, Kim discovered he had a woman in his hotel room despite the fact that he said he was fighting to get Kourtney back.

This led to an explosive confrontation as Kim searched Disick's suite to find the woman and eventually found her, telling her to get out of the room.

MJ and Kris had an emotional interview with each other.

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Kris wanted to interview MJ on tape to be able to learn more about her mother. E!

To preserve MJ's memories about herself and their family, Kris interviewed her for a video they could have after she's gone.

It turned into an emotional moment shared by this mother and daughter and became even more tear-jerking when MJ asked Kris questions, too.

Kim and longtime assistant Stephanie Shepherd went their separate ways.

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Stephanie Shepherd was previously Kim Kardashian West's assistant. Instagram/steph_shep

After a rumor spread that the Kardashians had fired the long-time assistant, Shepherd explained in a video of Kim's app that she wanted to leave to grow her own career instead of someone else's.

Kim also addressed their working relationship on "KUWTK." 

"Stephanie and I have decided to part ways," Kardashian said on the show. "She wanted a different role and I was going in a different direction, so for both of us, I just felt like it wasn't the right fit anymore.

Kim added: "She's really been there for me. So I said, 'I love you so much, and maybe this is good to push you to figure out what you want to do. ' It ended really well. She knew that she needed this time and that it wasn't working."

Kylie hid her pregnancy from everyone.

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People were guessing about Kylie Jenner's pregnancy for months. Kylie Jenner/YouTube

When rumors about Kylie's pregnancy were at their height, she stopped appearing on the show altogether.

But then, she showed up pregnant on "KUWTK" in season 15, proving that she had actually been filming for the show in secret.

Disick began dating Sofia Richie.

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Scott Disick and Sofia Richie broke up in 2020. Romain Maurice/Stringer/Getty Images

When Disick, who was 34 at the time, began dating the model, then 19, the family was shocked and teased him about the age difference.

But in the end, Kris and Kim gave Disick their support, and Richie was even seen on vacation with Kourtney, Disick, and their children.

The family confronted Tristan Thompson about reports that he cheated on Khloe.

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Cheating rumors broke one day before Khloe went into labor. E!

We knew it was coming, but in season 15 fans got to watch the family learn about Thompson's cheating scandal just days before Khloe gave birth to their daughter True.

Unsurprisingly, Khloe's sisters were angry, but Khloe tried to keep her cool for her daughter's arrival.

Disick was angry after finding out Kourtney had a boyfriend.

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Younes Bendjima and Kourtney Kardashian dated for nearly two years. Gabriel Olsen/Getty Images

Disick was angry when he found out that Kourtney was dating Younes Bendjima, which led to him making drunken phone calls to her in the middle of the night and later threatening Younes and his friends while they were all in Cannes.

"He goes, 'You better watch your back — your little friend is going to get beat up,'" Kourtney later told her sisters.

Kim claimed she was high on ecstasy when she filmed her now-infamous sex tape.

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Kim Kardashian West appeared on "KUWTK." E!

While trying to prove her wild side to Disick and Kendall, she admitted to taking ecstasy twice. One of the instances was when she got married for the first time, and the other was when she filmed her sex tape with ex Ray J.

"I did ecstasy once, I got married. I did it again and I made a sex tape," Kim said. "Like, everything bad would happen."

Kim and Kourtney fought over the family's Christmas card.

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Kim Kardashian West on "KUWTK." E!

In season 15, Kourtney and Kim had one of their most explosive fights ever when they couldn't come to an agreement about when they were going to shoot their family Christmas card.

"I need Kourtney to not be so f---ing annoying with a stick up her a-- like she runs this s--- because she doesn't," Kim said at the time. "She is the least exciting to look at, so she can be out."

Khloe and Malika had a fight.

Malika Haqq on "KUWTK." E!

Feeling left out with how much time Khloe spent in Cleveland with Thompson, Haqq had a rare argument with her best friend.

"It is a bit of a strain. I don't wanna blame you because you moved. That's so childish. But I think it's hard. You and I, we went from seeing each other how many days a week to seeing each other every other month," Haqq said

It seemed like they might not be able to salvage their friendship at the time, but they were able to work things out.

Khloe had to put her dog down.

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Gabbana was the family dog but lived with Khloe Kardashian for a long time. Instagram/KhloeKardashian

On season 15 of "KUWTK," Khloe's dog, Gabbana was getting older and weaker. After rushing Gabanna to the hospital one night, Khloe learned that she had developed fast-spreading cancer. Kardashian then made the decision to put Gabbana down.

The scene was difficult to watch, especially since the dog had been present on the show for many years.

Kendall made headlines for her role in a Pepsi commercial.

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Kendall Jenner in the now-pulled Pepsi ad. PepsiCo

Pepsi's commercial made waves when they released an ad featuring Jenner giving a Pepsi to a police officer in the midst of a protest. The ad was criticized for appearing tone-deaf for suggesting you can end police brutality with soda.

While Pepsi originally stood by the ad, they eventually removed it.

Jenner didn't address the controversy immediately but eventually, on the show, Jenner tearfully talked about the ad saying, "Obviously, if I knew that this was going to be the outcome, I would have never done something like this."

She added, "I trusted everyone. I trusted the teams, but after I saw the reaction and I read what people had to say about it, I most definitely saw what went wrong. I was so stuck, and I really didn't know what to do, that I completely shut down."

Kim returned to Paris for the first time since her robbery.

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Kanye West and Kim Kardashian West at the Louis Vuitton show in Paris. Chesnot/WireImage

On a season 15 episode of the show, Kim returned to Paris for the first time since her robbery, attending Virgil Abloh's Louis Vuitton fashion show.

Although she was nervous, she still went on the trip, and by the time she came back, she felt like she'd be able to return again for a longer stay in the future.

Khloe found out that Thompson cheated on her with family friend Jordyn Woods.

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Khloe Kardashian appears on "Keeping Up With the Kardashians." imageSPACE/MediaPunch/IPx/AP

On a season 16 episode of the reality show, Khloe and her family reacted to the news that Thompson kissed Woods at a party

Larsa Pippen opened the floodgates by calling Kim to tell her that she'd heard the NBA player hooked up with the model, who was then Kylie's best friend, at a party.

Khloe then called Woods to ask her what happened, and Woods told the reality star that she couldn't remember whether they kissed or not.

The sisters then patched Kylie into the call to get her opinion, and the makeup mogul agreed that Woods' behavior was "very weird." Khloe said that Woods eventually admitted that they did kiss.

And Thompson, who was on a flight when the string of calls were made, confirmed that something happened between him and Woods. 

"I'm so heartbroken and so like — what is this? Is this life?" Khloe said. "Right now I don't feel much of anything. It's like I'm in shock. A lot is happening. This is a debilitating blow to my soul. It's so humiliating, it's hard, and there are some days you just want to cry."

The cheating scandal caused Kylie to sever ties with Woods, who previously lived in the Kylie Cosmetics founder's home

"I called her and she didn't really say anything," Kylie said. "She was just like, you know, crying the whole time, and I was just telling her, 'I'm scared of you now, that you're capable of waking up the next morning with a smile on your face.' Then I pretty much told her exactly what we've been talking about  — like, 'You weren't thinking about True, not Khloe, not me.' You can do whatever, but when it affects my family, me, that's when it's a problem."

Kim changed the name of her shapewear line, Kimono, at the request of the mayor of Kyoto.

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Kim Kardashian West started the brand SKIMS. E!

Kim announced her shapewear line, Kimono Solutionwear, in June 2019.

People accused the reality star of cultural appropriation for referencing a kimono, which is a traditional Japanese garment that originated in the 17th century and continues to be the national dress of Japan.

On a season 17 episode of "KUWTK," Kim revealed that it would cost $10 million to rename the line. 

"In a perfect world, if I could just say, 'Let's change the name,' and it would be that easy, then I would do it in a heartbeat," she told Disick. 

After the mayor of Kyoto, Daisaku Kadokawa, wrote Kim a letter explaining the significance of the kimono in Japanese culture, the reality star said she had "an understanding" and changed the name to SKIMS instead. 

The family impersonated each other.

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Kendall Jenner imitated her sister Kylie Jenner. E! / Kylie Jenner/YouTube

The Kardashian-Jenner family showed just how well they know each other on a season 17 episode of "KUWTK"

Kendall dressed up as Kylie and applied over-the-top makeup to her face and arm, mocking the Kylie Cosmetics founder.

Khloe took on the role of Kris, barking orders at her assistant and making sure everyone in the room knew the whereabouts of her Birkin bag.

Kourtney mocked Kim and her "effortless" wardrobe of sweatpants and leggings, making a point to say that it's actually "a lot of effort" and requires seven stylists.

Kim shot back by showing up to dinner late as Kourtney, seeming displeased and saying she was "pooshing" through life alone.  

Kris chatted about her sex life with Corey Gamble at lunch with her daughters.

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Khloe Kardashian and Kendall Jenner appear on "Keeping Up With the Kardashians." E!

Kris met up with her daughters Khloe and Kendall for lunch on a season 18 episode of "KUWTK."

As soon the 64-year-old reality star joined them at the table, she asked "Do I have lipstick all over my face? We were just having a little make-out session in the car," referring to herself and her boyfriend Corey Gamble.

The remainder of the lunch included numerous innuendos from Kris about her sex life with Gamble — like asking if her shirt was on correctly and saying she could "rub" the tiramisu on her body — leaving Khloe and Kendall visibly uncomfortable. 

Kim and Kourtney got into a physical brawl.

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Kourtney and Kim Kardashian get into an argument in the 18th season of their reality show. E!/YouTube

Kim and Kourtney's issues reached a boiling point during a season 18 episode of "KUWTK."

When the SKIMS founder implied that Kourtney doesn't "care about stuff," the eldest sister snapped back at her and said she would "f--- you up." Kourtney pushed Kim to the ground, leading Kim to threaten to punch her sister in the face. 

The sisters then began grabbing and hitting each other until Khloe stepped in to separate them. 

Production took a week-long break after the fight, and Kourtney announced that she was stepping back from the show

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