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Kris Jenner Says Her 'Biggest Life Regret' Had To Do With Caitlyn Jenner & Another Man

Photo: @kourtneykardashian / Instagram; lev radin / Shutterstock
Caitlyn Jenner, Robert Kardashian, Kris Jenner

Kris Jenner opened up about her past choices during a heart-to-heart conversation with her daughter Khloé Kardashian on a new episode of "The Kardashians," which aired on October 26, 2023. 

As Khloé contemplated cutting her ex and the father to her two children, Tristan Thompson, out of her life, her mother offered her some sage wisdom about letting people go.

Kris Jenner said her ‘biggest life regret’ was cheating on Robert Kardashian.

Kris and Robert were married from 1978 until 1991, expanding their family with the births of their children, Kim, Kourtney, Khloé, and Rob. Kris owned up to cheating on Robert twice during the course of their marriage — once with a man named Todd Waterman, and later, with Caitlyn Jenner (formerly Bruce Jenner), who publicly came out as transgender in 2015.



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When Kris and Caitlyn met in 1990, her divorce was one year away from being finalized. In a recent interview with The Times, Caitlyn noted the instant connection the two had. She explained, "We hit it off right at the beginning, and we were married after five and a half months... I’d have to say, it was love at first sight."

In a vulnerable and tender exchange, Khloé asked Kris what was going through her head that led her to cheat on Robert. Kris gave a candid response, noting that, in part, her infidelity occurred due to "being really young and dumb… because you don’t really understand the consequences of your actions."

Khloé kept gently pressing Kris, in the way that daughters often do, when they want to know more about their parent’s inner world. She asked, "What was my dad not doing that made you want to look elsewhere?"

Kris answered Khloé’s probing question by admitting she wasn’t entirely sure what her initial reasons for cheating on Robert were. "I don't know because he was such a great husband and such a great dad, and I think that I fell into a situation where I thought that the grass was greener somewhere else, and I made a huge mistake,” Kris said. “That’s my life’s biggest regret."

Kris’s decision to cheat on Robert seems to have been centered on feeling like she was missing out on something or someone else, and less on who her first husband was as a person.

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While so much of the Jenner-Kardashian family lifestyle feels unrelatable, Kris’ admission of regret was a truly resonant moment.

She described the way her relationship with Robert shifted after their divorce, saying, "When I got divorced, Robert and I became best friends. We talked on the phone all day long, helped each other through things all the time, and I did have regrets.”

Kris hoped Khloé would take her past regrets into account when deciding how to navigate her relationship with Thompson in the future. She said, "I want Khloé to be really careful when she makes these decisions and she has to let somebody go."

The fact that Kris wondered if some other person might be a better option than the husband she had is an incredibly common feeling. Who hasn’t looked at how their life unfolded and thought, “If only I had done things differently”?

Thinking that the grass is greener with someone else is an easy mindset to fall into, especially when we’ve grown comfortable in our relationships.

As barber and influencer Vic Blends noted on TikTok, “The grass is not greener on the other side; the grass is greener where you water it.”



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Blends explained, “Everybody’s yard looks better than yours because you have never done what was necessary to grow your own. It takes discipline to grow. It takes sacrifices to grow. And more importantly, it’s going to take patience to grow.”

What’s striking is that Kris was able to admit that cheating on Robert was a huge regret.

While Kris admitting this doesn’t change her past actions, it does shed light on the complexity of maintaining romantic relationships.

One thing that Kris doesn’t regret is speaking her truth and revealing that she had affairs. As she explained in an interview with Oprah, she regrets getting divorced, yet she sees the silver linings that bloomed due to that split — the births of Kendall and Kylie, her younger daughters, who she had with Caitlyn. 



She explained how she takes that regret and “turns it around [and] I always say, ‘Kendall and Kylie.’”

Living a life without regrets is an impossible feat. Making mistakes and having regrets is part of what makes us human. Yet as Kris shows, sometimes our regrets lead us to other parts of our lives that never would have existed otherwise. 

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Alexandra Blogier is a writer on YourTango's news and entertainment team. She covers celebrity gossip, pop culture analysis and all things to do with the entertainment industry.