Kris Jenner admits that cheating on Robert Kardashian Sr was the “biggest regret” of her life

In the latest episode of ‘The Kardashians’ Khloé Kardashian put her momager Kris Jenner in the hot seat by asking, "What was your mindset when you cheated?" referring to Kris’s extramarital liaison with soccer player Todd Waterman in 1989 whilst she was still married to Khloé’s father, famed attorney Robert Kardashian Sr. 

Kris has previously spoken about cheating on Robert, who went on after their divorce to defend OJ Simpson during Simpson’s famous murder trial in 1994, but off the top of the episode, Kris goes into full detail about her regrets of cheating, and how the father of her four children (Kourtney, Kimberly, Khloé, Robert Jr) became a close confidant.

Off the top of Thursday’s episode, the “Good American” founder goes in hard on her mother, asking about her infidelity, “When you did that with my dad, and you had four kids and you had a family? Yes, I know you were really young...."

Kris took the inquisition rather well, responding, "being really young and dumb is something that plays into it because you don’t really understand the consequences of your actions."

The conversation was spurred by Kris inquiring as to whether Khloé would want to get back together with Canadian basketball star Tristan Thompson after his series of infidelities in their relationship.

"But what was my dad not doing that made you want to look elsewhere?" Khloé pressed her mom.

"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,” Kris admitted, “and I made a huge mistake.”

“That’s my life’s biggest regret," she revealed. Kris and Robert Kardashian Sr were married from 1978 to 1991. Kris then married Caitlyn Jenner after 5 months of dating, and only one month after her divorce from Robert was finalized in 1991. They were married until 2013 when Caitlyn revealed she was transgender.

This isn’t the first time Kris has called her breakup with Robert Sr a huge regret. Back in 2020, on the “In Charge with DVF” podcast,  she said, “I got married when I was very, very young. I met Robert when I was 18 years old. We dated for four years, got married at 22, sooner or later during my life when I was in my 30s, I had an affair and my biggest regret was the fact that it broke up my family.”

Robert Kardashian Sr died in 2003 after a battle with esophageal cancer. 

In the episode’s confessional, Kris then went into detail about her relationship with Robert Sr after they split. 

"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," she detailed.  "I thought, Wow, what I was thinking? So I want Khloé to be really careful when she makes these decisions and she has to let somebody go."

She continued, "I'm not proud of the way I behaved during that time, but you know what? Everything happens for a reason.”

"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 [Jenner]."

Kris is currently in a relationship with talent manager Corey Gamble. They have been dating since 2014.