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Kris Jenner Describes Her Affair with Caitlyn as Her ‘Greatest Regret

Kris and Caitlyn Jenner
Kris and Caitlyn Jenner (Credits: The Today Show)

Kris Jenner takes pride in many aspects of her life, but there is one particular episode that is shrouded in regret. On a recent episode of “The Kardashians,” Kris, aged 67, had a heart-to-heart conversation with her daughter Khloé Kardashian about an affair she had with Caitlyn Jenner while still married to Robert Kardashian Sr. She revealed that this is the “biggest regret” of her life.

This revelation came about as Khloé probed her mother about the reasons behind her infidelity, saying, “What was your mindset when you cheated? When you did that with my dad, and you had four kids and a family? Yes, I know you were really young….” Kris responded with composure, acknowledging the role of youth and naivety, explaining, “Being really young and dumb is something that plays into it because you don’t really understand the consequences of your actions.”

Khloé continued to seek understanding, asking what her father might have lacked that led her mother to look elsewhere. Kris candidly admitted, “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.”

Kris and Caitlyn Jenner

Kris and Caitlyn Jenner (Credits: Vanity Fair)

In a confessional interview, Kris elaborated on her hope that Khloé would consider her choices carefully, especially concerning Tristan Thompson, the father of Khloé’s children, True and Tatum. She drew from her own experience, recalling how she and Robert became best friends after their divorce, supporting each other through life’s challenges and having regrets of her own. Kris emphasized, “So I want Khloé to be really careful when she makes these decisions, and she has to let somebody go.”

Despite her remorse, Kris also expressed a belief in fate and divine plans. She acknowledged, “I’m not proud of the way I behaved during that time, but you know what? Everything happens for a reason.” Kris revealed that she lives her life with the belief that there’s a greater purpose, noting that without the events of her past, she wouldn’t have her daughters, Kendall and Kylie Jenner.

Kris and Robert Sr. were married from July 1978 to March 1991, during which they welcomed four children: Kourtney, Kim, Khloé, and Robert Jr. Kris met Caitlyn in 1990, a year before her divorce from Robert Sr. was finalized. In a recent interview, Kris shared that they hit it off from the start and were married just five and a half months later, describing it as “love at first sight.” They tied the knot in April 1991, one month after her divorce from Robert Sr. was official. Their marriage lasted 22 years before their separation in 2013 and their subsequent divorce in December 2014.

Following her divorce from Robert Sr., they remained close friends. Robert gained national attention as an attorney during O.J. Simpson’s notorious 1994 murder trial and was diagnosed with esophageal cancer in July 2003, passing away less than two months later on September 30, 2003, at the age of 59.

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