Kris Jenner Opened Up About Her Biggest Regret In Life: ‘I Didn’t Know What To Do’

Kris Jenner may be a momager extraordinaire today, but in her 30s, she was like so many women just trying to figure things out. Kris reflected on that time in her life during an appearance on designer Diane Von Furstenberg's podcast, InCharge With DVF.

Kris opened up about the unusual path her life took that landed her and her family where they are today. Of course, that path begins with Robert Kardashian Sr. Kris explains how she met the famed lawyer and entrepreneur at just 18 years old. They married when she was 22, and over the next eight years, they grew a family together.

About a year after her fourth child, son Rob Kardashian, was born, Kris found herself questioning her wonderful life. The time of doubt led to an affair that ultimately ended her marriage. The OJ Simpson trial would also drive a wedge between the two, although they eventually reached better terms. Robert died in 2003 of esophageal cancer just two months after being diagnosed.

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In the conversation, Kris talks about her marriage and the affair. On many occasions, Kris has referred to the affair as her life's greatest regret.

Kris Jenner has lived a fascinating life. She went from a single mother in her 30s who was divorced and confused about what was next to a verifiable mogul. In 2020 she opened up about that journey in conversation with Diane Von Furstenberg in Diane's podcast, InCharge With DVF.

At one point during the conversation, they discussed Kris' relationship with her first husband, Robert Kardashian. She was also open about her affair, which was the reason why the marriage ended. Kris has previously noted this as one of her biggest regrets.

"I got married when I was very, very young. I met Robert when I was 18 years old," she explains. "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."

"I didn't know what to do," Kris continued. "I had four kids. I was single. I didn't know where I was going to live. I didn't know what I was going to do. I didn't know how I was going to make a living. It was the scariest time to be that young."

"I think I was 32 years old, and I had four children. My son was maybe a year old, and it was scary. I was really, really scared. I remember picking myself up by my bootstraps one day," Kris continued.

It was her faith in God that helped pull her through that difficult time.

"I have deep faith in God. I just started praying that God would just strengthen me, give me that power, give me the ability to be in charge of my own life," Kris explained.

"It was my turn to really grow up."

As far as why the affair happened, Kris touched on it during a 2018 sit-down with TMZ's Harvey Levin. "I married Robert when I was 22 years old and I got pregnant on my honeymoon — I had the happiest life you could’ve dreamt about," she recalled.

"But when you’re in something, sometimes people think the grass is always greener and that was like what I think I went through at some point."

Kris' affair was with then-professional soccer player Todd Waterman. Although Kris initially declined to comment on rumors of this affair, she has since been open about it.

"I did, I did," she said. "Which wasn’t — nothing I’m proud of. When I look back on it now, probably one of my biggest regrets in my life is that that marriage fell apart."

As hard as the split was on Kris and Robert, it would have a lasting effect on the Kardashian kids. During a 2012 episode of Keeping Up With the Kardashians, a then-pregnant Kourtney lashed out at her mom for divulging details of the affair in a memoir.

As the oldest, Kourtney had the most vivid recollection of the decline of her parents' marriage. Although Kourtney claimed she would never understand how Kris could do that to her family, a therapist helped her work through her emotions on the matter.

Kourtney is definitely more at peace with what happened between her parents today. She even noted that she's modeled her co-parenting relationship with ex-boyfriend Scott Disick after the one between Kris and Robert.

"I know with my parents, as soon as everyone got along, life was so much easier. It felt like everyone was happy," Kourtney said in a 2019 episode.

Kim also remembers the affair as it was happening. In a 2012 interview with Oprah, Kim was very open about the fact that they protected their dad because they knew he never wanted to split with Kris.

"Always in life we always protected our dad because we felt bad for him because he didn’t want the divorce," Kim said at the time. "We knew it was our mom’s fault and we were well aware."

While Kim and Kourtney knew what was going on, Khloé and Rob did not. Khloé learned the truth when she was older. Rob didn't find out until his mother's memoir. For Khloé, her parents' relationship after the divorce helped mold her into the parent she is today.

"I was about 4 or 5 when they divorced," Khloé said on the Divorce Sucks podcast. "I always remember how amazing [they were]. Now that I've gone through it myself trying to co-parent — they were so seamless with it."

"I never, ever heard my parents talk disrespectfully about the other one," she continued. "My parents were so good at not letting us feel whatever they were going through."

While Kris regrets how things dissolved between her and Robert, everything does happen for a reason. Following the divorce, she got together with Bruce Jenner, who has since transitioned to become Caitlyn Jenner.

Through their marriage came two more daughters, Kendall and Kylie, something the momager wouldn't trade for the world. Robert and Bruce were also able to maintain a friendly relationship, which helped the Kardashian kids bond with him on a deeper level, even after Robert's death.