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Kris Jenner revealed to her daughter Khloé Kardashian that cheating on her father, Robert Kardashian Sr., with soccer player-turned-animator Todd Waterman in 1989 is her "life's biggest regret."
During their conversation, Kris explained that being young and naive played into her actions, and she didn't fully understand the consequences at the time.
Khloé still wasn't fully understanding and asked her mom again, "But what was my dad not doing that made you want to look elsewhere?"
Kris then 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 Robert were married for over two decades and had four children together: Kourtney, Kim, Khloé, and Rob. Despite their eventual divorce, Kris emphasized the love and respect she had for Robert, who passed away in 2003. She shared that her infidelity was a turning point in their relationship and has haunted her ever since.
“I constantly lied to Robert” during the affair, Jenner wrote in her 2011 autobiography, “Kris Jenner … And All Things Kardashian.” “I could not control myself.” Kardashian caught her and her lover meeting for breakfast — she thought he had her followed by a private detective — which led to a huge fight. This would go on for three months, with him catching them together three times.
He eventually filed for a divorce, and the split was finalized in March 1991. Jenner remarried a month later — less than a year after getting fixed up with Caitlyn Jenner on a blind date.