The Most Uncomfortable Kardashian TV Moments Ever

If you choose to document your everyday life, catching the odd, uncomfortable moment on camera becomes pretty much inevitable. In fact, when it comes to reality TV, part of the appeal as a viewer is getting a ringside seat to all of those gloriously awkward situations, and Keeping Up with the Kardashians has had plenty of those since it premiered in 2007.

Some of the most cringe-worthy moments in the history of the show happened in those early days, long before Kimye was a thing and Caitlyn Jenner was still going by the name Bruce. KUWTK has evolved somewhat since then, but the family is still prone to the odd disaster, both on and off the show. Kendall Jenner's controversial 2017 Pepsi commercial is just one moment in a long list of highly uncomfortable ones. From huge tantrums and awkward interviews to epic fails on stage, these are the most uncomfortable Kardashian TV moments ever.

Forgetting someone's name is always awkward, but try forgetting a name as you're staring down a TV camera in front of a live audience. That's exactly what happened to Kendall Jenner at the 2014 Billboard Music Awards as she introduced Australian boy band 5 Seconds of Summer. The reality star looked beyond embarrassed as she fumbled through her intro, almost mistaking 5SOS for One Direction. "You guys, I'm the worst reader," she said, which only upped the cringe factor.

Billboard blamed "teleprompter issues" and invited Kendall and her sister Kylie Jenner to return the following year to introduce a live Kanye West performance. They were booed by the audience as they introduced West, and the siblings ended the night on bad terms because Kendall (worried she'd be grilled about their dad's recent transition announcement) decided to bail on press interviews, leaving Kylie to face the media's questions about Caitlyn Jenner alone — that session didn't go well.

"Kendall ditched me," Kylie later told Kim Kardashian on Keeping up with the Kardashians (via Look). "She was supposed to do the interviews with me ... I was looking around for Kendall and she wasn't there. I didn't know what to say." 

The Jenner sisters made up later in the episode. "I'm sorry and I think next time we will communicate better," Kendall said.

The Kardashians have been on some pretty fancy vacations over the years, but they haven't always had the best of luck when they've traveled. Kim Kardashian was famously robbed at gunpoint in a Paris hotel room in 2016, handing over millions of dollars worth of jewellery to armed intruders. It was an ordeal that nobody should have to go through, but it wasn't quite as easy to feel sorry for the reality star that time she cried like a baby over losing an earring in the ocean.

There were no thieves involved when she visited the French Polynesian paradise of Bora Bora — just Kardashian's now ex-husband Kris Humphries. During an episode of Keeping up with the Kardashians, the former basketball star tosses Kardashian into the ocean before she has the chance to remove a pair of diamond studs worth $75,000 apiece. When she realizes one is missing, the waterworks are instant, prompting a now iconic response from sister Kourtney Kardashian: "Kim, there's people that are dying."

The missing earring was found, but Kim's bratty reaction would last forever in meme form. She defended her tantrum during E!'s 10th anniversary special in 2017, telling viewers that while she could "see Kourtney's point now," people just don't realize how much those jewels mean to her. "I have upgraded that pair of diamond studs," she said. "I worked really hard."

In a 2009 episode of Keeping up with the Kardashians, a young Rob Kardashian had to seek medical advice after his morning coffee left him suffering from an unusual side effect — one that just wouldn't go away. Kardashian had unwittingly picked up the coffee that Kris Jenner had fixed for Bruce Jenner, which apparently contained a hefty dose of Viagra (via Celebuzz).

After speaking to a doctor and realizing what had happened, Kris comes clean to her then-husband. "I think that he might have accidentally drank some coffee that I had intended for you to drink that had a little, kind of like a male enhancing little drug thing," she says, right in front of their son. The moment is particularly embarrassing for Bruce (who years later, as Caitlyn Jenner, admitted that she "wasn't entirely comfortable" having sex with Kris during their marriage). 

Many suspected that the whole situation was a set-up. "It's difficult to tell how much of this whole plot was fabricated for TV," former Jezebel staffer Tracie Egan Morrissey said of the incident. "But even if it was 100 percent fake, that somehow makes it even crazier — that they'd actually agree to going along with a storyline that involves mothers and boners."

It seems like a lifetime ago that Rob Kardashian was drinking his step-dad's Viagra-laced coffee and laughing about it. In fact, it seems like a lifetime ago that he laughed at anything at all. His involvement in Keeping up with the Kardashians has lessened considerably over the years, with the Kardashian brother becoming a total recluse at one stage. His weight has fluctuated dramatically as he's struggled with depression and anxiety stemming from his numerous failed relationships.

He went through a particularly nasty break-up with his baby mama, Blac Chyna, who accused him of domestic violence. Not long after Chyna made her allegations, footage emerged that showed Kardashian slapping his ex-partner, Adrienne Bailon, during a heated argument. In the clip, he berates Bailon for "calling off the f****** wedding in India" and strikes her across the face as she tries to leave. His mother and sisters immediately jump to Bailon's defense and began hurling abuse at him.

Making this whole situation even weirder: According to Gossip Cop, the slap (which was from an early episode of Keeping up with the Kardashians) was supposedly a joke that Bailon was in on.

Scott Disick and Kourtney Kardashian had three children together over the course of an on-off relationship that was constantly dogged by allegations of unfaithfulness. Disick's reputation as a womanizer has made for some pretty uncomfortable viewing over the years, but it all came to a head when the family visited Costa Rica during a 2017 episode of Keeping up with the Kardashians. Despite his baby mama and her family being present, Disick decided to bring a female companion along for the trip, which made for one of the most cringe-worthy dinners in KUWTK history.

"It's pretty obvious that the girls know something's up," Disick says of the tense atmosphere at dinner, which was a traditional Costa Rican banquet complete with a fire show from the locals. "Nobody really wants to say what's on their mind, and if this dinner isn't awkward enough, these fire dancers have to come out and start doing hula-hoops. I mean, I already felt under fire!" 

After being scolded by the mother of his children for being "inappropriate" and "disrespectful" to her and the family, Khloe Kardashian steps in and decides to help cool Disick down by tossing her water right at him. 

The origin of the Kardashians' fame is often traced back to a sex tape that Kim Kardashian made with former boyfriend, Ray J. After the tape leaked in 2007, Kardashian shot to prominence and brought her family along for the ride. The Kardashian name soon became a household one, and in 2011, the family was among Barbara Walters' most fascinating people of the year. Accompanied by momager Kris Jenner as well as sisters Khloe Kardashian and Kourtney Kardashian, Kim sat down for an interview with the veteran broadcast journalist, who pulled no punches during what turned out to be a highly uncomfortable chat.

"You're all often described as famous for being famous," Walters says with little enthusiasm. "You don't really act; you don't sing; you don't dance. You don't have any — forgive me — any talent!" Khloe tells Walters that they're still entertaining people regardless of their lack of traditional talents. "None of us think we have talent," she responds. "None of us think we can sing or act or dance." Kim adds, "It's more of a challenge for you to go on a reality show and get people to fall in love with you for being you."

The conversation gets even more awkward when Walters brings up the infamous sex tape, asking Kim if she regrets making it. "I've made mistakes in my life, for sure," she replies.

The Kardashian family tree can get a little hard to follow sometimes, but what's important to remember here is that Brody and Brandon Jenner are Kim Kardashian's step-brothers and aren't related by blood. While this does make the fact that she's hooked up with one of them considerably less gross, this revelation still made for some thoroughly uncomfortable viewing during the family's 2014 trip to Thailand. 

During the vaca, Brody walks in on Kim taking some late night photos wearing nothing but a see-through dress. When they sit down for breakfast the following morning, Brody tells Kris that he liked what he saw. He then proceeds to rat out his brother, revealing that Brandon and Kim have kissed. According to TMZ, the pair hooked up before they were officially step-siblings during a raunchy game of truth or dare. Pretty awkward so far, but Brody isn't done.

On the following episode, he apparently thinks it's a good idea to strip naked on Kim's bed and wait to be discovered. "This is so gross. I do not want to see you," she jokes when she discovers Brody in the buff. "Hopefully this just puts an end to this really awkward game," she says.

Kim Kardashian was involved in another super-cringey moment during the aforementioned vacation to Thailand while ziplining. When the reality star has second thoughts about the high-flying activity, she urges sister Khloe Kardashian to go first. Khloe does just that, with little fuss, but her bravery does little to calm Kim's nerves. Despite words of encouragement from Bruce Jenner (who tells her to "man up" and get on with it,) Kim freaks out big time and starts crying. She causes quite the scene after being told by the bemused local instructors that it's a "one-way ticket" deal.

"It's really crazy, because when you become a mom, every decision that you make is just different," Kim says later. "Like, I'm thinking, 'Do I really care to do this when I could be with my daughter?'" 

Entertainment Tonight called her out for playing the "mom card," pointing out that it wasn't the first time Kim used the waterworks to get her way on KUWTK.

In 2015, news anchor John Brown left Good Day Orlando viewers gobsmacked when he walked off set mid-broadcast in protest of the show's relentless reporting on the activities of the Kardashians. After being asked to discuss the fact that Kylie Jenner had named her new bunny rabbit Bruce, Brown stood up and stormed off, leaving co-host Amy Kaufeldt to carry on alone.

"I'm having a good Friday, so I refuse to talk about the Kardashians," Brown rants as he walked out of shot. "I've had enough of the Kardashians! I can't take any more Kardashian stories on this show! I'm sick of this family, I can't take it anymore! It's a non-story! We're talking about this family every freakin' day on this show! Nobody cares about this family anymore!"

The clip went viral, forcing Brown to address his outburst on the following show. "My issue isn't with the Kardashians," he clarifies. "I don't have a problem with them at all, I've never seen the show. My issue is from the media standpoint, we feel like the public wants to hear it. The public hears it so much about it that they think the media is going to give more and it's this huge cycle."

Tristan Thompson has been accused of cheating on baby mama Khloé Kardashian on numerous occasions, and there's been plenty of eye-witness, photographic, and video evidence to fuel those claims up. The NBA star was even said to have been unfaithful to Kardashian during her pregnancy, though he somehow managed to avoid being kicked to the curb. His luck ran out in February 2019, however, when allegations emerged that he'd cheated again — this time with Kylie Jenner's best friend.

Thompson came clean about his hook-up with Jordyn Woods, who (after initially denying anything had happened) admitted to kissing the father of Khloé's child. Woods was living with Jenner at the time, though that arrangement ended swiftly. Woods was essentially excommunicated from the Kardashian clan, who cut ties with her on social media and IRL. All of this went down while season 16 of Keeping Up with the Kardashians was partially filmed, which meant that when the season premiered, Thompson and Kardashian were very much still an item. 

The first episode made for some pretty uncomfortable viewing. Fans of the long-running reality show had to watch Kardashian declare her love for a man they knew had already cheated on her. Again. "Watching Khloé act so happy and in love is truly painful," Cosmopolitan said of the season opener. "...Things get even sadder during Khloé's on-camera interview when she muses, 'I have come to a place in my life where I am super comfortable.'"

When Khloé Kardashian and her sisters sat down with Jimmy Kimmel in April 2019, she once again had to field questions about her complicated relationship with Tristan Thompson. Unwilling to dodge the touchy subject, Kimmel straight-up quizzed the Good American co-founder about her love life, and it was more than a little awkward. "I do want to ask about this character that you had a baby with," Kimmel said. "Is it time to stop dating basketball players?" 

The reality star handled the personal line of questioning like the seasoned pro she is, but her face revealed that she was not happy. "I don't know, you know," she said, barely able to maintain a smile. "I like what I like. What can I say?" Kimmel went on to ask Kardashian if she even liked basketball. Cosmopolitan was just one of many outlets that found the whole exchange "rude" and "peak awkward," noting that Kardashian "looked supremely uncomfortable" answering questions about her ex.

Elle also found the interview cringe-worthy, though the lifestyle mag gave props to Kardashian for keeping her cool. "I should probably like, start to date accountants or something like that," she said.

When Kourtney Kardashian turned 40 in 2019, exes Scott Disick and Younes Bendjima attended her birthday bash, as did Kim's former BFF Paris Hilton. Kim and Hilton even recorded some videos together, dancing the night away like it was the early 2000s again. Kim shared plenty of other moments from the party on social media, but Khloé shared a different kind of video — one intended to embarrass her sister on her big day.

Back in 2016, Kourtney appeared live via satellite on Australian talk show Today Extra. The interview took place not long after Kim was robbed by gunmen in Paris, so naturally, the topic came up in conversation. "How is everyone going and how is Kim doing?" co-host David Campbell asked. Kourtney clearly wasn't in the mood to discuss the subject, however. In fact, she didn't seem to want to discuss anything, period. The reality TV star unexpectedly froze on the spot, going completely silent despite no apparent connection issues.

According to News.com.au, Kourtney's publicists were off-camera urging her not to answer the question about Kim, which created a long, uncomfortable silence. "All right, it looks like Kourtney doesn't really want to go there," co-host Sonia Kruger eventually says. "I think she's blanking me," Campbell says. "She's totally blanking me on that question." 

When Khloé resurrected that interview on Instagram (via the Daily Mail), she called it the "most awkward video ever."

It's hard to argue against the notion that the Kardashian empire was built on Kim K's leaked sex tape, considering the first season of Keeping Up with the Kardashians dealt largely with the fallout of that leaked footage. Conspiracy theorists believe momager Kris Jenner was actually involved in the leak, but there's no way of knowing for sure. What's undeniable is that the tape made Kim famous, though she can't exactly tell her daughter that.

North West is at an age where she's starting to ask questions about fame. In Season 16 of KUWTK, North asks her mom why there's a flock of photographers waiting for them outside every single morning, and Kim's attempts to explain the origins of her fame make for some rather uncomfortable viewing. "To get very technical — my name is Kim Kardashian," she says. "And Daddy is Kanye West. And Daddy is a singer, performer, artiste. Mommy ... has so many talents I can't even begin to name them."

The clip got quite the reaction on social media, so much so that Jimmy Kimmel asked about it when the Kardashians appeared on his show. "I was obviously a little bit joking," Kim tells him. "Kourtney and I have sat our kids down and had little conversations with them. As they get older, we'll continue to have that conversation." Here's hoping those conversations will also take place in front of the KUWTK cameras.