Kris Jenner Reveals Her "Life's Biggest Regret"
Matthew Alvarez
Published Feb 22, 2026
Kris Jenner has lived a lot of life, from being married twice and welcoming six children, to starring on reality TV and starting multiple businesses. But, in her 67 years, there is one choice that Jenner regrets more than anything else, and she opened up about it on the latest episode of her family's Hulu series The Kardashians. During a conversation with daughter Khloé Kardashian, Jenner shared that her biggest regret is cheating on her first husband, Robert Kardashian Sr., during their marriage, which lasted from 1978 to 1991. During their time together, Jenner and Robert welcomed four children: Kourtney, Kim, Khloé, and Robert Kardashian Jr.
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Jenner and Khloé were discussing Khloé's ex and the father of her two children, Tristan Thompson, cheating on her repeatedly during their relationship when Khloé brought up her mother's past infidelity. As reported by People, Khloé asked, "What was your mindset when you cheated? When you did that with my dad, and you had four kids and you had a family?" Jenner responded that "being really young and dumb is something that plays into it because you don't really understand the consequences of your actions."
Khloé wanted to know more about why her mother would go through with being unfaithful. "What was my dad not doing that made you want to look elsewhere?" the 39-year-old asked. Jenner told her daughter, "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. That's my life's biggest regret."
Jenner cheated on Robert with a man named Todd Waterman, who, according to Vanity Fair, is an animator and former soccer player. Jenner opened up in detail about her relationship with Waterman in her 2011 memoir Kris Jenner…And All Things Kardashian. Waterman appeared on a 2012 episode of Keeping Up With the Kardashians, when he and Jenner met up for a conversation after not seeing one another for years.
On the show, Jenner's children expressed concern about her being in contact with her ex-fling again, and her then-spouse Caitlyn Jenner was also upset about the turn of events. Waterman was brought up again in a 2018 episode in which Kourtney and Jenner spoke about the affair.
Now, Jenner has said that while she regrets her infidelity, she believes it set her on the path that led to her two youngest children, Kendall and Kylie Jenner, because she and Robert split up not long after. Jenner married Caitlyn soon after her divorce from Robert in 1991, they welcomed Kendall and Kylie together, and in 2015, they divorced after over 20 years of marriage.
"I'm not proud of way I behaved during that time, but you know what? Everything happens for a reason," Kris told Khloé of her past. "I really do live my life by thinking God has a plan, and without that whole thing happening, there never would've been Kendall and Kylie."
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Lia Beck Lia Beck is a writer living in Richmond, Virginia. In addition to Best Life, she has written for Refinery29, Bustle, Hello Giggles, InStyle, and more.Read moreFiled UnderCelebrities • Entertainment • NewsRead This NextCaitlyn Jenner No Longer Speaks to Kris
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