Kris Jenner Struggles to Be as Proud as Kim Kardashian Is About Sex Tape in Midseason Finale

"Don't be ashamed," Kim said proudly while the whole family was participating in a media training session, in which the ladies all practiced answering questions about Caitlyn Jenner, Kendall Jenner's controversial Pepsi commercial, Rob Kardashian's meltdown and Kim's sex tape.

"Kris, interestingly, your eyes dropped when Jen got to the mention of the tape," one of the coaches told the momager after being pressed about a Hollywood Reporter headline, "The Kardashian Decade: How a Sex Tape Lead to a Billion Dollar Brand."

Another sensitive topic for Kris was mention of her ex's tell-all book, which covered family life with the Kardashians as Bruce before transitioning into life as a woman.

"What were some of the most hurtful things in Caitlyn's book?" the coach asked.

"Well, I think just the general tone of the book," Kris said. "Very mean-spirited. A lot of inaccuracies. I think somebody with a little elegance and class and somebody that's been divorced, but trying to stay on good terms with the family might have written, 'Wow, married to her, didn't work out, she's a great girl, wish it could have been different.'"

But Kris admitted the thing that stung the most was that Kendall and Kylie Jenner being forced to keep "a lot" of their father's secrets over the years.

"There were things that happened that they didn't tell me because they were told not to," Kris said. "I'm not resentful about it, it just makes me really sad because I'm a protective mom. I would do anything for my kids and had I known some of the things they were experiencing - it just broke my heart hearing some of that stuff."

Kendall was told to be much more direct in her answers when talking about lessons she learned from participating in that infamous Pepsi commercial. And as for Khloé Kardashian's thoughts about Rob's explosive fight with his ex-finacé and baby mama Blac Chyna, the reality star said her brother is just a big lover.

"Rob definitely wears his heart on his sleeve and when he loves, he loves really, really, hard," she said. "With that being said, when he gets hurt, he hurts really, really badly."