One of the highlights from Sunday's Keeping Up with the Kardashians 10th anniversary special was when Ryan Seacrest asked Kris Jenner and company to dig deep and talk about their most difficult days on the show.
With her daughters looking on, Kris revealed that Caitlyn Jenner's transition was the absolute toughest for her.
"To have someone have a camera on you and recording your emotions and your moments, I think that's probably mine," said Kris, who was also shown sobbing in the kitchen in a clip. "If I remember correctly, one of the camera guys started crying. It was rough. It was a rough day."
Khloé's toughest day also came around the time of Caitlyn's transition in 2015. "I was really protective and I wasn't fully informed," she said on the special. "With Lamar [Odom and the break-up], there was no secret.
"I was more afraid of how people would accept your father and I didn't want anyone to ever be mean to your dad," Khloé said, motioning to Kendall and Kylie. "I didn't know what I was allowed to say, what not to say."
For Kylie, "everything that went on" with Caitlyn was tough. "Honestly, I am so happy that my dad is finally living her true self," she said. "I'm completely supportive. I've always been. I feel like she did it at the right time, when Kendall and I were much older."
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Kim said her toughest day arrived in 2007, when stolen nude photos of a 17-year-old Kourtney were being shopped around 10 years after she had taken them with an ex-boyfriend. As KUWTK fans may recall, the ordeal eventually involved the FBI, since Kourtney was underage in the photos, and the family dealt with it on the season one finale, aptly titled 'The Price of Fame'.
As Kim said on Sunday's special: "I can handle if it's about me, [but] if I hurt someone else, then that's when I can't handle it. I remember crying, I was just so upset. I thought Kourtney would never speak to me again."
The discussion also led Kendall to open up about the day she thought Lamar had died after Kim texted her news that turned out to be from a fake e-mail account. "I immediately started sobbing on the plane. Then I got the next text saying, 'Actually, he's OK. He's alive'. I was so upset."
Last but not least, Kourtney and Scott sort of dodged the topic and instead, Kourt praised her ex for always checking in on the family no matter what.
"Even if he feels like he did something that makes everybody angry, he still will come in and show his face and be there with us, which I feel like is a good thing," she said. "He is who he is. He's not going to hide and not see anybody."
Kim also had nice things to say about Scott, adding: "Sometimes when you've had a moment you weren't proud of, you show up to check if we're OK. [You're] always checking on Kourtney, it's really respectable, even if you had done something really f**ked up, you care."
Keeping Up with the Kardashians premiered on October 14, 2007.
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Peggy is Cosmopolitan.com’s entertainment writer, specializing in Leonardo DiCaprio, This Is Us, and the royals. She’s also a proud Canadian and pug lover. When Peggy’s not obsessing over Leo’s latest lover or gut size, she can be found watching old episodes of Friends or Gilmore Girls. Her dream is to one day live on a pug farm and write children’s books, with illustrations by her very talented husband Greg.
