The Most Memorable Moments from Each Season of Keeping Up with the Kardashians

Season 1: ‘You’re Doing Amazing, Sweetie’

Kris Jenner convinced Kim Kardashian to pose for Playboy and “You’re doing amazing, sweetie,” was born. This was right after Kim’s sex tape scandal had rocked the family — and helped them gain fame.

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Season 2: Momager for Life

Remember when Kim dated football player Reggie Bush? Do you also remember when Kris ended up selling a very private, very sexy calendar that Kim shot ~*for Reggie’s eyes only?*~

Don’t worry, Kim got her mom back by selling a risqué photo of her wearing nothing but her then-husband’s gold medal and an American flag.

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Season 3: ‘Your Sister’s Going to Jail’

When Khloé Kardashian was arrested for driving under the influence, she was originally sentenced to community service and ordered to complete a DUI course. Khloé then violated her probation, which meant she would have to serve time in jail … but her older sister could not stop taking selfies on the way there. In the words of Kris: “Kim, would you stop taking pictures of yourself? Your sister’s going to jail.”

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Season 4: Speedy Nuptials 

Khloé met basketball player Lamar Odom in August 2009 and married him just one month later. The pair knew each other for 21 days before he proposed, and were wed nine days later.

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Season 4: Up Close & Personal Birth

Kourtney Kardashian decided to give birth to her first child, Mason Dash Disick, on national television, but no one expected her to reach down and pull her own child from her birth canal.

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Season 5: Kim’s Fling with Her Bodyguard

Kim was very, very single (and she made sure to let everyone know it) after ending things with Reggie Bush (and then Miles Austin), and she decided that her Australian bodyguard, Shengo, was fair game.

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Season 6: Kim Marries Kris Humphries 

Who could forget the televised marriage of Kim and Kris Humphries, a relationship that ended after 72 days? That happened on season 6 of the show. No, really, like within one season of Keeping Up with the Kardashians, Humphries and Kardashian went from dating to engaged to tying the knot.

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Season 6: Kim Loses Her Earring

Oh, and in this season Kim also lost her diamond earring in the ocean (don’t worry, Kylie found it) and prompted Kourtney to say the iconic, “Kim, there’s people that are dying.”

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Season 7: Kim’s Split

Okay, so technically this photo is from Kourtney & Kim Take New York, but in season 7 we got a front-row seat as Kim made the decision to divorce Kris Humphries after 72 days of marriage. In an iconic episode from that season, her sisters had to pretty much stage an intervention when she started wearing wigs as a means of coping.

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Season 8: Kimye Is Expecting! 

While in the middle of her divorce proceedings with Humphries, Kim and then-boyfriend (now estranged husband) Kanye West announced that they were expecting their first child, a girl, whom they would name North.

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Season 9: An Epic ($3 Million) Proposal

Kanye surprised Kim by proposing to her on the field of San Francisco’s Oracle Park, in front of an orchestra, her entire family and a jumbotron.

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Season 10: Caitlyn Jenner Causes Drama in the Family

After Kris and Caitlyn Jenner decided to separate, Jenner confirmed her transition from male to female and revealed her new identity as Caitlyn in June 2015. That meant that viewers also got to see her family’s unfiltered reactions. Things turned sour after Caitlyn gave an interview to Vanity Fair that wasn’t very kind to Kris and the three oldest Kardashian daughters, causing a rift in the family.

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Season 11: Khloé & Lamar Officially Divorce

On Oct. 15, 2015, Odom was found unconscious in a brothel in Nevada after an apparent drug overdose, forcing Khloé to make the choice to put their divorce proceedings on pause so that she could help him heal. Their divorce wouldn’t be finalized until Dec. 17. 2016.

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Season 12: Rob Proposes to Blac Chyna

Rob Kardashian shocked his family when he proposed to then-girlfriend Blac Chyna without telling any of them about it. Chyna shares a son with Kylie’s ex-boyfriend, Tyga, and had been friends with Amber Rose, an ex of Kanye West, now Kim’s ex. Needless to say, it was all pretty awkward.

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Season 12: A Kardashian Baby on the Way

On top of the surprise engagement, the family also found out that Chyna was expecting just a few months later. But Rob and Chyna would split in February 2017, shortly after their daughter Dream was born.

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Season 13: The Aftermath of Kim’s Paris Robbery

In October 2016, Kim was robbed in Paris, prompting her to take a break from public events and social media, and leaving her traumatized. The robbery itself was not filmed, but in the weeks and months after, Kim was still dealing with her anxiety.

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Season 14: 2 (Well, 3) Babies on the Way

Kim and Khloé both announced in season 14 that they were expecting children! Khloé with her boyfriend Tristan Thompson, and Kim with Kanye via a surrogate. As we now know, their sister, Kylie Jenner, was also expecting, though she chose not to publicize or film her pregnancy for the show.

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Season 15: Tristan’s (First) Cheating Scandal

Days before Khloé was due to give birth, reports surfaced that Tristan had cheated on her. Khloé’s family rushed to be with her in Cleveland, and Tristan was present for the birth of the pair’s daughter, True Thompson. That didn’t mean that things weren’t a little awkward in the delivery room, though.

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Season 15: The ‘Triplets’ Arrive

It’s 2018, and three Kardashian-Jenner babies are born! Chicago West on Jan. 15, Stormi Webster on Feb. 1 and True Thompson on Apr. 12. We found out why we saw so little of Kylie on the show that season: She had been hiding her pregnancy from us all.

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Season 16: Tristan Cheats on Khloé with Jordyn Woods 

In one of the biggest Kardashian-Jenner shockers of all time, Tristan was caught cheating again, but this time with close friend of the family, Jordyn Woods. Khloé had to experience the betrayal on television, just as she had when Tristan cheated on her the season before. Woods insisted that Thompson kissed her after partying with him at his home, but admitted that she should not have been with him to begin with.

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Season 17: Scott and Corey Argue Over Parenting

Kris Jenner’s boyfriend Corey Gamble doesn’t usually get involved in the family’s overarching drama, but in season 17, he and Scott Disick got into it over dinner.

It all started when Kourtney told the table that she no longer had a nanny because her then-7-year-old daughter Penelope scratched her. 

That is when Gamble suggested that Disick should “discipline” his daughter Penelope by spanking her.

“If P scratch me, I’m whipping her a–,” said Gamble.

“My daughter?” Disick replied, visibly shocked and angry. The fight only escalated from there, with Kourtney eventually telling her mother “he will never be with my kids alone and if he does that in front of any of us there will be a f—ing issue,” before leaving. 

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Season 18: Kim & Kourtney Get Into a Physical Fight

On the season 18 premiere, Kourtney and Kim got into an aggressive argument stemming from Kourtney’s boundaries when it comes to filming the reality show. After Kim accused her sister of not having a strong work ethic, the pair started to argue verbally. 

The fight escalated to actual blows after Kim expressed her frustration with her sister’s work ethic — or, in her opinion, lack thereof. 

“We shut down production for a week after that,” Kim said on The Tonight Show: At Home Edition. “I think everyone was really shook for a minute and just was like, ‘This isn’t our type of show. We want everyone to be comfortable and safe.’”

“But, you know, that happened. And I don’t really ever resort to violence that, but she scratched me so hard,” she continued. “I was bleeding. You didn’t really get to see that detail, but when I looked down at my arm and I saw she had really scratched me … I just went over and slapped her back. It’s not my proudest moment, but we were going through it.”

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Season 19: Kylie & Kendall Get Into a Fight

Close siblings were at it again on season 19, when the family took a quick trip to Palm Springs. After getting into a tiff over an outfit, Kendall and Kylie really got into it on the drive home to Los Angeles (with Kris’ boyfriend Corey Gamble in the car with them), arguing about whether or not they’d drop Kendall at her home before things turned aggressive. Nearly one month afterward, Khloé and Kris helped them patch things up.

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