Kris Jenner Reveals Her “Life’s Biggest Regret”

DFree / Shutterstock
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 .
RELATED: Barbra Streisand Says Marlon Brando Propositioned Her With His Wife in the Next Room .
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.”
Barbra Streisand Says Marlon Brando Propositioned Her With His Wife in the Next Room

Ron Galella, Ltd./Ron Galella Collection via Getty Images; Ron Galella/Ron Galella Collection via Getty Images
If her upcoming memoir clocking in at 992 pages is any indication, Barbra Streisand has a lot of stories to tell. One particularly scandalous one involves late actor Marlon Brando , who became a friend of the star. According to Streisand’s book, Brando once propositioned her while his wife was in the very next room. The Oscar-winner turned him down, but it wasn’t the end of their relationship. It also wasn’t the last time that he hit on her.
Read on to find out more about Streisand and Brando’s relationship, which traces back to her crush on him before they ever met.
RELATED: Ali MacGraw “Knew” She’d Have Affair With Co-Star Steve McQueen: “I Was Obsessed.”

Bettmann / Getty Images
Streisand was interviewed by Vanity Fair ahead of the Nov. 7 release of her memoir, My Name Is Barbra . The profile recaps a chapter of the book titled “Brando,” in which Streisand writes that the actor asked her to have sex with him while they were at a party in 1966. At the time, she would have been 24 while Brando was 42.
According to the book, Brando told Streisand, “I’d like to [expletive] you” while his wife was in an adjoining room. (The article does not state which wife was present, however. Brando had overlapping marriages with Movita Castaneda and Tarita Teriipaia , though the Castaneda marriage was later annulled.)
RELATED: Elizabeth Taylor’s Affair With This Actor Was So Scandalous, the Vatican Got Involved .

Fotos International/Getty Images
According to her book, Streisand and Brando became friends and stayed that way until his death in 2004. The now-81-year-old also writes that after Brando saw the 1968 film adaptation of Funny Girl , he called her and said, “You were really good, but you run funny.” Vanity Fair ‘s Radhika Jones told Streisand that “Brando” is “one of the wilder chapters [she’s] ever encountered in literature.” The author responded, “Well, he’s Marlon Brando!”
View this post on Instagram A post shared by John Travolta (@johntravolta)
During a 2012 appearance on Piers Morgan Tonight , Streisand told another story about spending time with Brando. This one was about a road trip they took together in the ’70s.
“[Brando] wanted to take me to the desert, to see the wildflowers,” she said, adding that he said he wanted to “sleep over in a ghost town.”
Streisand said that she rejected his advances. “I was such a nice Jewish girl that I just said, ‘Marlon, I can’t stay overnight with you. I’ll go with you for the day.’” Again, she added that they remained friends and would talk on the phone “for hours and hours.”
Evidence of Streisand and Brando’s friendship was shared by John Travolta in on Instagram in 2020 . In a “flashback Friday” post, Travolta shared a photo of himself, his late wife Kelly Preston , Streisand, her husband James Brolin , Brando, and others. In the picture, Streisand sits on Brando’s lap. Travolta wrote in the caption, “A special party for Marlon Brando at Barbra Streisand’s house #FBF.” He did not specify what year the photo was taken.
Long before they ever met, Brando became Streisand’s celebrity crush after she saw him in 1955’s Guys and Dolls .
“Since I was 13, Marlon Brando was my favorite. I saw him in Guys and Dolls —and that was it,” she told W magazine in 2016. “Interestingly, there was a period of 27 years when I didn’t sing in public, because of stage fright, and when I finally did, I created a scenario in which I sang ‘I’ll Know’ with Marlon Brando in Guys and Dolls . I put myself in his movie! I invited Brando to my house to see the piece, and he made me take him through my entire show. We then watched a movie together. It was wonderful: He was my idol, my biggest crush.”
“I’ll Know” is a song from the Guys and Dolls . When Streisand performed the song at Madison Square Garden for her 1994 live album The Concert , she spoke about Brando and the film before singing it.
“This friend of mine named Barbara Sankell , who knew that I wanted to be an actress told me about this actor named Marlon Brando, who was in a movie called Guys and Dolls , which I also didn’t know was from a Broadway play. And so I went to see it, and it was truly a life-altering experience seeing Marlon Brando for the first time. It was the only movie that I ever sat through twice—just to get to see him again and to have another Mello Roll. Anyway, I’ll never forget this song.”