Strange Things About Kris Jenner's Marriages

The world may be fixated on the ever-changing and salacious love lives of the Kardashian-Jenner siblings. But, their mom, Kristen "Kris" Jenner, has a pretty fascinating relationship history of her own.

It all started around the time she met famed defense attorney Robert Kardashian Sr. Jenner was working as a flight attendant, according to Harper's Bazaar, and she bid the tarmac adieu, married Kardashian at the age of 22, and immediately got to work expanding their family. Following the births of Kourtney, Kim, Khloe, and Robert Jr., their marriage hit the skids. Jenner bounced back after their divorce by marrying former Olympian, Bruce Jenner (now known as Caitlyn). And that marriage didn't turn out too well either. 

The Keeping Up with the Kardashians matriarch may be a legit businesswoman, having propelled her family into superstardom, but some would say she's a novice when it comes to managing her rather strange romantic liaisons. Her failed marriages have been full of cheating allegations and rumors that she married for money instead of love.

We ain't saying she's a gold digger, but she has found a way to get involved in some pretty weird relationships — even by Hollywood standards. Here are all the strange things about Kris Jenner's marriages.

Is she all about the Benjamins?

Kris Jenner's allegedly less-than-wholesome ways apparently started at a very early age, if you believe author Jerry Oppenheimer's recount of her life story in his book, The Kardashians: An American Drama (via Page Six).

According to the author, Jenner dated the late professional golfer Cesar Sanudo when she was 17 years old, and he was 10 years older than her. During a trip to a horse track, she met Robert Kardashian and reportedly cheated on Sanudo with the high-profile attorney who famously represented O.J. Simpson during his 1995 murder trial. Jack Spradlin, a friend of Sanudo's, said: "[Kris] saw a far better financial opportunity with Kardashian than with Cesar."

After a brief breakup, in which Kardashian took some time to pursue Elvis Presley's ex-wife, Priscilla, he and Jenner reconnected, and she reportedly moved into his Beverly Hills, Calif. mansion right away. 

They tied the knot in 1978, and Jenner reportedly began draining her new hubby dry by making lavish purchases, including a $3,000 belt. "I just sensed that Kris saw in Bob a kind of gold mine," Kardashian's former pastor, Kenn Gulliksen, told the author. 

With mo' money in their bank account, Jenner and Kardashian's marriage got bogged down by even mo' problems...

Her new girls allegedly made her restless

According to The Kardashians: An American Drama (via Page Six), Kris Jenner underwent a mommy makeover after giving birth to their son, Robert Jr., and became the proud owner of some breast implants.

With her altered bod in place, Jenner allegedly went on a quest to regain just a smidgen of the freedom she lost when she became a Beverly Hills housewife, reportedly telling her then-husband, "I need to go out. I need to have fun."

Instead of being at home with the kids, Jenner was supposedly out reliving her youth and making up for lost time."[She] was coming home at 2 and 3 in the morning drunk, and she would tell Robert, 'I have four kids and I have not lived life,'" an insider told the author. 

Clearly the larger issues at play here were the fact that Kris got married at a relatively young age and perhaps wasn't quite ready to tackle motherhood, but darn those bewbs. They ruined everything!

She's a big cheater

Kris Jenner appeared on Fox News' OBJECTified and finally talked about her first marriage. "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 told the host. "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."

That's when Jenner dished the dirt on herself that she was doing the nasty with a soccer player while she was married to the late attorney. Even though she was very upfront about her past indiscretion, she also admitted she wasn't proud of being an adulterer. "When I look back on it now, probably one of my biggest regrets in my life is that that marriage [to Kardashian] fell apart," she said. But she also laughed off the fact that she was "kind of sort of" engaged to the aforementioned Cesar Sanudo when she met Kardashian. Sigh.

Are we the only ones cringing so hard right now? We give her props for being honest, but for the sake of her children, maybe Jenner didn't need to be quite so open about her infidelities. 

She flip-flopped on her love for Caitlyn

After screwing up her marriage to Robert Kardashian, Kris Jenner immediately moved on to Olympic gold medalist, Bruce Jenner — who now lives life as a transgender woman named Caitlyn.

Prior to Caitlyn's transition, Kris labeled him the love of her life in her 2013 memoir, Kris Jenner...and All Things Kardashian. But when Harper's Bazaar asked her if she still felt the same way in a February 2016 article, she stripped Caitlyn of that title. 

They say when you love someone, you love them forever, but that idea seems to have softened a bit for Kris, at least as far as Caitlyn is concerned. On the other hand, she had nothing but kind and loving words to say about her first husband. "I had a wonderful, beautiful life with Robert. He was just an amazing man," she said of the late lawyer who passed away in 2003 of cancer.

Of course, Kris also told OBJECTified that she believes the breakup of her marriage to Robert was "unfortunately the way it was supposed to go," because "it led me to another place where I then had Kendall and Kylie (her daughters to Caitlyn)." So, love lasts until the second fate decides you need to make babies with someone else? Got it. 

Out with the old hubby, in with the new

Radar Online dug up all the juicy details about Kris Jenner's 1991 divorce, including court documents where Robert Kardashian claimed he was forced to live with relatives during the divorce proceedings. He also claimed Kris had immediately moved in her then-boyfriend Bruce Jenner (Now Caitlyn) and his four children into the Beverly Hills, Calif. home she once shared with Kardashian!

"Firstly my children are exposed to another man living with their mother. I believe that is inappropriate and I ask the court to enjoin and restrain (Kris) from living with any member of the opposite sex in or about the presence of our children," Robert said in his request to the court.

To back up his claim, he described an incident in which their son, Robert Jr., was asleep on a couch in Kris' bedroom, while Kris was in the bed with Caitlyn! "In my option this situation is detrimental to the children," Robert reportedly stated.

Kris and the former world-class athlete would marry on April 21, 1991, just one month after Kris' divorce was finalized! 

She moves on quick, no?

She remained ringless forevsies

Kris Jenner told HuffPost about the day her second husband, Caitlyn, proposed to her at a restaurant after a day of house hunting. "He said, 'I am totally in love with you and would you marry me?' I was very surprised," Kris said.

Sounds like your typical engagement, right? Well, it was anything but orthodox, according to Kris, because Caitlyn didn't even bother to put a ring on it! "You know when I got a ring? A few months ago in Bora Bora. I got my ring for my twentieth anniversary," she told the publication.

Kris wasn't too ticked off about being engaged sans ring, though. She actually made a bunch of excuses as to why Caitlyn didn't present her with some bling. "We'd only known each other a few months [when we got engaged] and I don't think he really knew what my taste was. I'm really kind of picky about that stuff, in case you hadn't noticed. I'm very specific and he knew how anal I was. I'm kind of crazy that way," she said.

Is it really an engagement if there's no ring involved?

Friendly exes

Though the end of Kris Jenner's marriage to Robert Kardashian had more drama than an episode of Keeping Up With the Kardashians, things between them smoothed out a bit after Kris married Caitlyn. Believe it or not, Caitlyn and Robert even forged a friendship. "We [Robert and I] remained really, really close and had a really great parenting style with our kids. Then Bruce became really good friends with Robert, they would play golf together, so we've always had a one big happy family kind of a relationship," Kris told HuffPost.

A throwback photo Khloe Kardashian posted to Instagram was all the proof we needed that Robert was welcomed with open arms into Kris' new household. In the picture (above left), the late lawyer can be seen holding Kris' daughters, Kylie and Kendall Jenner, who were just itty bitty babies at the time. Aww.

"When you get married to me, I had four kids at the time, so you've got to get married to the kids. So I had the kids and I had an ex-husband. He got everyone's stamp of approval. Bruce was delicious," Kris said as she gushed about her then-husband.

We love that they were all able to get along, but it doesn't make it any less strange that her ex-husband and her new husband were so close. Do you think they exchanged horror stories about Kris while on the golf course?

Neighborly spouses

Viewers of Keeping Up With the Kardashians could feel the tension and discomfort between Kris and Caitlyn Jenner during the tail-end of their failed marriage. Kris was filmed being immersed in her children's careers, while Caitlyn was content with hanging out around the house, golfing, and flying her remote control helicopters.

Rumors emerged in 2013 that the then-couple's marriage was on the rocks, and Khloe Kardashian inadvertently spilled some strange information when she told The Tonight Show (via HuffPost): "They're not having problems, but they still like to live apart, which is definitely different [...] They got another house and Bruce stays there sometimes." A married couple living apart and we were supposed to believe everything was A-okay between them? Yeah, right.

Four months after that interview, Kris and Caitlyn announced they had split after 22 years of marriage in a joint statement published by E! NewsNeedless to say, no one was the least bit surprised by that announcement, especially after Khloe had already spilled the beans about their wacky living situation.

Did she cheat with a blast from the past?

In Touch Weekly claimed not only did Kris Jenner cheat on her first husband, but she had stepped out on Caitlyn Jenner, too, with a former soccer player named Todd Waterman. Sounds familiar, right? That's because Todd also just so happened to be the man with whom Kris admitted to cheating on Robert. (Hey, at least she's consistent, right?)  

Todd even made an appearance on KUWTK while Kris was still married to Caitlyn, and an insider told the publication that his feature on the program was allegedly Kris' way of "paying him off and making sure he stayed silent about their torrid past." 

Kris denied both the later cheating allegations and the payoff, but Todd told In Touch that back when Kris first moved Caitlyn into her Beverly Hills, Calif. home, he confirmed: "We were still sleeping together when she started dating Bruce." Yikes! 

Regardless of the supposed second affair, it's still pretty strange that Kris would flaunt her former flame in front of her then-husband and millions of television viewers, right?

An exercise video-turned-sex tape

As rumors began to swell that Kris and Caitlyn Jenner's marriage was headed toward splitsville, the former spouses attempted to stick a fork in all of the gossip during a September 2013 episode of KUWTK (via the Independent).

In the episode, Kris admitted that she and Caitlyn had taken cues from her daughter, Kim Kardashian, by co-starring in their own sex tape. Are you cringing yet?

While Kris was eager to drop the news on her unsuspecting children, Caitlyn was much more reserved. But Caitlyn finally admitted their on-camera romp started off as an exercise video, and things got so heated between them, it escalated into a full-blown sex tape. We could've lived the rest of our lives without knowing what turned Kris and Caitlyn on TBH.

To explain their filmed rendezvous, they insisted it was their way of changing things up to keep their marriage spicy. Too bad it didn't have the type of affect they were looking for.

'KUWTK' first, marriage second

With one divorce underneath her belt, one would think Kris Jenner would've rolled up her sleeves and put in some hardcore effort into keeping things with Caitlyn Jenner afloat. But multiple sources confirmed that before the then-couple was on the outs, Kris was way too preoccupied with attaining power and fame to be bothered by her then-marriage.

What started out as a whirlwind romance between the once-smitten couple went haywire when Kris and her family were tapped to appear in the long-running E! reality series, KUWTK. "Bruce never wanted the circus that came with the show," an insider spilled to People. "He just went along with it. It was fun at first, but then it started to run their lives."

The source added: "Everything in Kris's life is about ratings," before revealing that Caitlyn was "never [Kris'] priority and he was totally sick of it."

Hmm...perhaps if Kris were more present in her then-marriage, she would've remembered the intimate details Caitlyn reportedly shared with her about her gender issues, topics Kris insisted were never discussed during their marriage. Just sayin'.

What's next for the two-time divorcée?

As weird as her past marriages have been, we weren't surprised when Kris Jenner told Ellen Degeneres she was hesitant about walking down the aisle for a third time, despite being in a relationship with road manager Corey Gamble since 2014. "You know, I've done that twice and it didn't work out so well. So I don't know — you never know," she said.

But Jenner's uneasiness appeared to change when she appeared on The Late Late Show in 2018. During a game of Spill Your Guts or Fill Your Guts - where host James Corden and Jenner took turns between answering tough questions or eating nasty food – Corden brought up the humongous diamond ring Jenner had been wearing on her ring finger. 

Instead of flat-out denying she was engaged to Gamble, and saving herself from eating a critter, Jenner refused to answer the question and gobbled up an insect instead, while cameras cut to Gamble who was standing backstage with the biggest smile on his face.

If she does choose to say a third set of vows, we wish her nothing but the best, including a happy and long-lasting marriage!