The momager recently sat down for an interview with Fox News Channel's OBJECTified that touched on her first marriage to Robert Kardashian Sr., and the affair that led to the end of her marriage.
Far from the first time she's discussed the subject, many of her kids have also opened up about their feelings regarding the affair with soccer player-turned-animator Todd Waterman.
Jenner and Kardashian were married from 1978-1991 and welcomed four children together: Kourtney, 39, Kim, 37, Khloé, 34, and Rob, 31.
Scroll through to see all the things the Kardashians have said about the end of her marriage.
"I married Robert when I was 22 years old and I got pregnant on my honeymoon — I had the happiest life you could've dreamt about," she recalls to host Harvey Levin. "But when you're in something, sometimes people think the grass is always greener and that was like what I think I went through at some point."
When asked about her "affair with a soccer player," Jenner admitted that it happened.
"I did, I did," she said. "Which wasn't — nothing I'm proud of. When I look back on it now, probably one of my biggest regrets in my life is that that marriage fell apart."
"I saw how it destroyed my dad," Khloé Kardashian said in 2016 on an episode of talk show Kocktails With Khloé. "I saw what it did to my dad, so I don't want to do that. I also saw the regret from my mom."
"I don't understand how you can do that to your family," the mother of three said in a 2012 episode of Keeping Up with the Kardashians.
She continued to her mom, "You're so inappropriate and embarrassing. You have no shame in your game."
As Jenner grew visibly upset, Kourtney decided, "I don't want to keep talking about this. I just don't relate to this and I don't understand it."
Kim Kardashian West
Kris ran into Waterman at the Toluca Lake Tennis Club back in 2012 and they exchanged email addresses, as Jenner felt the former lovers had unfinished business. But Kim wanted her mom to stay away from him.
"Do you want to still be married?" Kim asked Jenner in an episode of their show. "Then stay far away from him. He already ruined your first marriage. Seriously."
Kardashian continued in an on-screen interview, "It's a little scary having my mom run into this guy that changed her life so much. If he was able to break up a marriage with four kids, you just hope that there's no feelings left there." (At the time, she was still married to Caitlyn Jenner, then known as Bruce.)
"I just hope that mom learned her lesson the first time," she added to her brother Rob.
"If she messes up at this age, she's done," he said. "Because why would you want to start over?"
"I've spent the most time with this guy," she said. "I remember, like, activities I did with him. You had pool parties at the house downstairs with him. I remember them."
She continued, "This whole Todd situation is uncomfortable for me in general. I was around 4 and I, of course, at 4, do not know that Todd is not supposed to be around. My mom was young. We all make mistakes, but why are you still talking about it? I feel like this chapter in your life should be way closed."
"Why do you want to play with fire?" the Good American jeans founder questioned her mother. "Why do you want to see him again?"
Kourtney Puts her Foot Down
After discussing the subject with her sisters in the following episode, Kourtney decided: "I definitely don't think my mom should be in any sort of contact with Todd, especially after the past. I think that there's no good that would ever come from talking to somebody like that."
Can you Keep Up?
The Royal Family of reality television will be back for its highly-anticipated 15th season this August, as Kim Kardashian West revealed in the latest trailer.
"Oh, hey guys. It's Kimberly. Remember me?" Kardashian West tells the camera as it zooms in toward her face. The video then transforms into a collage of snippets from upcoming scenes from the show featuring the members of the Kardashian Jenner clan.
"Did you miss us? Because we missed you," she says. "But don't worry, you didn't miss anything."
Keeping Up With the Kardashians season 15 premieres Sunday, Aug. 5 at 9 p.m. ET on E!