Kris Jenner Might Be Getting Married… Again!

Most people know Kris Jenner as the world-renowned momager and matriarch of the Kardashian-Jenner kids. The multi-millionaire businesswoman has spent most of her life focused on her children’s relationships and careers, but she is now turning her attention to the not-so-new man in her life, Corey Gamble.

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The 66-year-old has six children from her first two marriages and has been dating Gamble since 2014. After going through two tough divorces, Kris has rethought the idea of marriage. She and Gamble might be serious about each other, but will there be wedding bells in their future? Keep reading to find out.

It Started With an Affair

Before we get into Kris’s current relationship, let’s go back to the beginning, when she met Robert Kardashian. In the spring of 1973, Kris, then known as Kristen Mary Houghten, was 17 and dating pro-golfer Cesar Sanudo. He was out of town often, and Kris found ways to occupy herself.

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On one occasion, Kris decided to go to the Del Mar racetrack in California, where she met 28-year-old Robert Kardashian. He was infatuated with her, but she was still dating Sanudo. Since her boyfriend was away, Kris brought Kardashian to their house to fool around, but Sanudo caught them.

He Wanted Her Back

When Kris and Sanudo’s relationship ended, she dated Kardashian for a while before he ran off to be with Priscilla Presley. His relationship with Presley didn’t last long, and Kardashian went running back to Kris. The high-profile lawyer could provide her with the life she dreamed of, but she didn’t want to settle down.

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Kris was a flight attendant and wanted to see the world. When Kardashian proposed to her, she rejected him. However, he was persistent and popped the question a second time, and Kris didn’t refuse. The two married in 1978 when she was just 22 and moved to Beverly Hills.

One Big Happy Family

A year after their wedding, Kris gave birth to their first daughter, Kourtney. The couple then expanded their family with three more children: Kimberly, Khloe, and Robert Jr. They were the typical country-club family, spending their weekends playing tennis with friends like OJ Simpson and his wife, Nicole Brown Simpson.

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It was the life of luxury Kris had always dreamed of, but she soon became a bored housewife. She didn’t have to work and loved her family, but something was missing. On the outside, they looked like a picture-perfect family, but things soon went downhill when Kris met Todd Waterman.

It Ended With an Affair

In the same way their relationship started, Kris and Kardashian’s relationship ended because of an affair. She found the excitement she craved in the arms of soccer star Todd Waterman. According to her 2011 memoir, Kris described the affair as “wild crazy sex all the time.” They also hooked up at a close friend’s home.

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However, Kris couldn’t hide the affair for long, and Kardashian eventually found out. He canceled her credit cards and ended the marriage. She hadn’t paid a bill since the day she married Kardashian, and suddenly, Kris had new responsibilities and had to pay her own bills. Still, she figured it out.

She Moved On

Before her divorce from Kardashian was finalized in 1991, Kris was set up on a blind date with Olympic gold medalist Caitlyn Jenner (then known as Bruce). Jenner was a dashing American icon, and Kris saw the potential in their relationship. Jenner was also friendly with Kardashian.

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In 1991, Jenner asked Kardashian for permission to marry Kris, and the two happily walked down the aisle. They were like the modern Brady Bunch because Jenner had four kids from previous relationships, and Kris also had four. Still, they wanted more kids.

She Started a New Job

By 1997, Kris and Jenner had two more children: Kendall and Kylie. Not only was she now a mother of six, but Kris also became Jenner’s manager. After not having a job for nearly 20 years, she saw potential in managing Jenner, who gave motivational speeches and other appearances.

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Jenner made good money, but the cash didn’t start rolling in until Kris scored Keeping Up With the Kardashians for the whole family. Kris and Jenner’s solid relationship was showcased for the first several seasons as they dealt with their children’s newfound fame.

It Wasn’t Perfect

Kris and Jenner had been married for 21 years when their relationship started to fall apart. Although their marriage was never perfect, the cracks became more evident when they started living apart around 2012. By early 2013, the couple decided to separate.

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The breakdown of their marriage was played out on KUWTK, but no one understood where things went wrong until Jenner came clean. A year after separating, Kris filed for divorce in 2014, citing irreconcilable differences. Kris said it was “the most passive-aggressive” breakup she had ever experienced.

Hurt and Betrayed

Shortly after their divorce, Jenner came out as transgender, taking the name Caitlyn. Kris had known Jenner took hormones in the 1980s but never understood that Jenner wanted to be a woman. Kris was confused but tried to support Jenner’s decision until Jenner bad-mouthed her in the press.

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Jenner dragged Kris through the mud, saying Kris was controlling and mean. She also claimed Kris knew she wanted to be a woman. While they might not have had the best marriage, Kris tried to be nice, but Jenner took every opportunity to hurt Kris.

Romance With the Bachelor

After separating from Jenner, Kris reportedly had a fling with Bachelor star Benjamin Flajnik in 2013. Despite the age difference, the two were on and off until April 2014. Kris didn’t mind the age difference, but she went through a lot during their time together.

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Kris has never confirmed her romance with Flajnik, but they would make an interesting couple. She was also focused on her crumbling marriage with Jenner, so the alleged fling with Flajnik was never serious. If anything, they fooled around and moved on.

A Younger Man

Kris is no stranger to dating men much younger, and a 25-year age gap didn’t turn her away from Corey Gamble. The ink was barely dry on her divorce papers when Kris met Gamble in 2014 at a party Kanye West threw for fashion designer Riccardo Tisci’s 40th birthday.

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Gamble noticed Kris first, and they started chatting. They had a lot in common because Gamble was a business executive and talent manager. Kris didn’t think it would be more than a summer fling, but they hit it off and kept in touch.

He Made the First Move

When Gamble saw Kris at the party, he was smitten. He waited till she was on her own and approached her. Gamble said, “I asked her to get up on stage and dance, so we started dancing.” He brought out Kris’s fun side.

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Kris enjoyed flirting with him; it felt good after a tough breakup with Jenner. She liked that he was bold, and Gamble was easy on the eyes. The two exchanged numbers at the party, but Kris didn’t have any expectations for Gamble.

Her Children Were Nosey

Kris and Gamble brought their relationship back from Ibiza, but she couldn’t hide it from her nosey children. Kris tried to keep it a secret, but Kendall, Kylie, and Scott Disick noticed she was glued to her phone more than usual and smiling when she got texts.

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They decided to spy on Kris’s cellphone and saw all the flirty texts between Kris and Gamble on an episode of KUWTK. Disick said, “ I don’t know if Kris googled how to be sexy over text, but she’s doing it.” They confronted her, asking who Corey was.

A Daughter’s Concerns

Kris regularly gives her children relationship advice, but the tables were turned when Kim shared her concerns about Gamble. Kim was living with Kris at the time and overheard the new couple getting frisky. She was worried about the age gap and didn’t know how serious things were.

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Kim wanted her mom to take things slow because Kris was still going through a divorce. She saw the new couple pictured together in gossip magazines and didn’t know if her mom had processed the breakup with Jenner. However, Kris assured Kim she was happy.

Going Public

No one is sure when Kris and Gamble made their relationship official, but they made their first public debut in October 2014. Gamble joined the family on a trip to Vegas to celebrate Kim Kardashian’s 34th birthday. They danced the night away at Tao nightclub.

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The following month, Gamble joined Kris and her friends to celebrate her 59th birthday. It seemed the pair had made their relationship official, but Kris kept quiet about their relationship. People asked her about Gamble, and Kris avoided answering because it was still new.

Everyone Questioned Him

When Kris and Gamble went public, her family had a lot of questions about her new boyfriend. They wondered why Gamble was at the high-profile party over the summer. It was later revealed that Gamble was working for Scooter Braun’s management company as Justin Bieber’s tour manager.

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Gamble ran in the same circles as the Kardashians, but Kris’s children still had questions about their large age gap. Gamble was a month younger than Kim, and the family wondered about his motives and intentions with their mom. The drama escalated from there.

Protective Children

Although Kris seemed happy in her new relationship, her children weren’t convinced that Gamble was right for her. Kourtney, Kim, and Khloe had seen their mom go through a difficult divorce, and they didn’t want her to get hurt again.

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Khloe wasn’t shy when she asked Gamble, “Have you always been attracted to older women?” Gamble replied, “Since I used to hit on my second-grade teacher. It’s not the age factor; it’s the connection.” It was still early in the relationship, but he won the family over.

Part of the Family

The longer Gamble and Kris dated, the more the family embraced him. He didn’t come from a big family and liked that Kris always had a full house. He also grew close to Kourtney because they were close in age. But Kendall still had questions.

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Because Kris and Gamble grew up at different times, Kendall wondered what they did together and what they had in common. Gamble reassured her that he and Kris had a lot in common. He told Kendall that Kris had a lot of energy, and it was better than being with someone young.

Too Close for Comfort

In 2016, Gamble started hanging out with Kourtney more often. He and the eldest Kardashian sister would go out to clubs and were seen on hikes. Kim said their friendship was weird, with Khloe referencing a picture of Gamble, Kourtney, and her kids that looked like a family photo.

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Gamble and Kourtney might have been spending a lot of time together, but Kris said everything was fine. She went as far as telling her children that she and Gamble engaged in “exhausting” activities. They didn’t want to hear further details, but Khloe still gave him a hard time.

Questioning Their Future

Seeing that Gamble was significantly younger, Khloe wondered if Gamble would want to get married and have children in the future. Kris was well past her childbearing years and had already been divorced twice. After speaking with Khloe, Kris confronted Gamble.

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Kris was happy with Gamble, but she didn’t want to hold him back from having a family someday. She had already raised six children and was a grandma, so she knew more children weren’t in her future. Luckily, Gamble was on the same page as her.

No Wedding Bells Here

It turns out that Kris doesn’t want to get married for a third time. She realized she didn’t want to deal with another marriage after two bad divorces, and Gamble didn’t mind. They loved each other and didn’t need a piece of paper to confirm that.

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Gamble also said he didn’t want children, and Kris had enough children and grandchildren for him to take care of. Even though they were on the same page, Gamble knew he would have to take a back seat to Kris’s businesses and children.

Was He Working for Them?

Gamble was often seen with the Kardashians even when Kris wasn’t around. Rumors started to arise that Gamble was more of a bodyguard than a family member. It didn’t help that he was in charge of getting more security guards after Kim’s Paris robbery and rushed to Kylie’s house when the alarm went off.

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Sources told Page Six that Kris gave Gamble a stipend to look after her kids when they went out. Friends of the family shot down the rumors, saying Gamble wasn’t in the relationship for money and truly loved Kris.

Breakup Rumors

Three years into their relationship, people speculated that Kris and Gamble had ended things. The rumors stemmed from a picture Kim posted on Instagram of Kris with the caption, “Caption this… SWF,” as in “single white female.” She quickly changed the caption, but it was too late.

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Kris never commented on the breakup rumors, but their relationship seemed fine. Deleting the caption also dispelled some of the rumors. Still, that wasn’t the only reason people thought Kris and Gamble’s relationship was on the rocks. Her kids had problems with him.

A Stand-Off With Khloe

Khloe and Gamble didn’t always see eye to eye, and she felt he didn’t like her. When Khloe shared the news of her pregnancy with her family in 2017, Gamble barely said congratulations. She didn’t understand what he had against her and voiced concerns to Kris.

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Khloe wanted everyone to get along for her mom’s sake, so she and Kourtney invited him for lunch. But Gamble didn’t make things easier. He said, “I’m a young dude dating your mom. Y’all are not my f***ing kids. We are technically peers.”

Things Didn’t Get Better

Khloe didn’t feel like things were resolved after the lunch, and things got worse. Kanye texted Gamble, asking why no one had ever met his family. Khloe agreed, telling her mom, “we tried to get to know him, but he has not been receptive.”

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Kris loved Gamble and wanted everyone to like him. However, she said her children always came first, and it seemed like she was questioning their relationship. Kris’s kids saw how hard it was on their mom and kept trying to make Gamble feel accepted.

Kris Defended Him

While her kids had their opinions, Kris put everything to rest. She told Khloe, “Nobody really slows down enough to take a look at it from a bird’s eye view of my life. I want you to recognize that when you question my relationship with Corey.”

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She told Khloe her feelings were hurt and added, “I think what you guys don’t realize is Corey is really taking care of me like no one ever has in my entire life.” Kris’s honesty silenced Khloe and her other children, and they even apologized to Gamble.

His Favorite Jenner

In 2020, Gamble made regular appearances on Kylie’s social media. He appeared in Tik Toks with Kris and Kylie and shared they had become close. In an episode of KUWTK, the family took a trip to Palm Springs to stay at Kris’s house, and Kylie had to come later than everyone.

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Gamble said he felt awkward around the rest of the family, but he was excited for Kylie to arrive because they were “best buddies.” When Kylie finally showed up, she and Gamble took shots together and had a fun time, but the night took a bad turn.

Getting in the Middle

Gamble should have learned not to get in the middle of family drama but forgot that during a night out in Palm Springs. Gamble, Kylie, and Kendall got in the same car to return to LA after a night out, and a fight ensued between the sisters.

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Kendall called her mom and sisters in a different car and sounded hysterical as she and Kylie yelled at each other. She told her mom that Gamble sided with Kylie and told her to “f**k off.” It didn’t look good, and Kris wanted to protect her daughter.

He Made Things Worse

When everyone had calmed down after the fight, Kendall confronted Gamble. He told her, “You’ve been a rude person for years. You’re an a**hole when you feel like it, and you get riled up for no reason.” He felt he didn’t owe her an apology, but this made Kris mad.

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She couldn’t believe Gamble would talk to her daughter like that. Although it didn’t happen in front of the cameras, Kendall and Gamble seemed to have patched things up. We can imagine that Kris had something to do with that.

The Drama Continued

Just as things started to get better with Kendall, Gamble got into a fight with Kourtney and Disick. When Kourtney told Gamble and her mom that her daughter Penelope scratched the nanny, Gamble had a strong reaction. He said he would “whoop P’s a**” if she ever scratched him.

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Kourtney and Disick were unhappy with Gamble’s comments, which exploded into a screaming match. Kourtney and Disick said Gamble would never be around their kids alone. Gamble worked things out with them, but the drama was stressful for Kris.

Things Have Gotten Better

Whatever issues Gamble has had with the Kardashian-Jenners, everything seems to be fine these days. Gamble accompanied Kris to Kim’s 40th birthday party in 2020 and was seen dancing and doing splits. He was the life of the party. Kris was happy to have everyone getting along.

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The family also put in extra effort to make Gamble feel special on his birthday. They surprised him and Kris with a trip to Napa for the day. It seems like Kris’s family has finally accepted Gamble, and hopefully, there won’t be any drama in the future.

Engagement Rumors

In 2018, Kris appeared on the Late Late Show with James Corden wearing a big ring. It looked like an engagement ring, and Corden asked if she and Gamble were engaged. Gamble was standing on the side of the stage, and Kris said, “it’s just a ring.”

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Kris put the rumors to rest after appearing on celebrity lawyer Laura Wasser’s podcast. The show about relationships, marriage, and divorce prompted Kris to explain why she’ll probably never marry Gamble. She confirmed they are happy with how things are.

An Unbalanced Relationship

While Kris and Gamble enjoy relaxing and vacationing together, they usually spend time doing things Kris enjoys. She was seen dragging him along to look at antiques, and he often appeared bored. Gamble suggested they try roller skating, but Kris used her bad knee as an excuse.

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It was clear to everyone that the relationship was one-sided. Kim said, “Mom and Corey’s relationship is 90 percent what my mom wants to do, and she doesn’t really bend and do what Corey wants.” Kim persuaded her mom to try activities that Gamble would enjoy.

Showing Her Love

Kris isn’t afraid to show her love for Gamble on social media. Every year on his birthday, she writes a long post, sharing how much she adores him. Kris has also posted several photos with her boyfriend, including their many red carpet and Met Gala appearances.

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Gamble is just as mushy and has posted about Kris since the early days of their relationship. When Jenner’s Diane Sawyer interview aired, Gamble showed his support for Kris by posting a picture of them together and writing how strong she was.

Are They Secretly Married?

When Kris recently moved into her new home, she told Khloe how helpful Gamble was with the move. She said, “He’s been so amazing moving into the house because he handles everything. I love that side of him because he is always protective.”

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Khloe also asked her mom about the huge yellow stone on her left ring finger. She said she heard from “four different people” that Kris and Gamble had a secret wedding. Kris laughed, “You think I’m going to get married and not have a massive party?” We can assume that means they aren’t married.

He Wasn’t at the Wedding

Although Kris hasn’t attended an event without Gamble in recent years, he was noticeably absent from Kourtney and Travis Barker’s Italian wedding in May 2022. Fans quickly noticed that Kris attended the big event on her own, leading people to question why Gamble wasn’t there.

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In the days after the wedding, rumors circulated that Gamble didn’t go because he was reportedly caught cheating on Kris. An Instagram account allegedly created by Kourtney’s oldest son Mason shared a post that Kris was cheated on. But she shut down those rumors.

Blissful Travelers

No one knows why Gamble didn’t go to Kourtney’s wedding, but he must have had a good reason because it was the event of the year. While many thought it was weird and speculated that he and Kris broke up, she dispelled rumors by posting a photo with him in June.

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Kris’s most recent post with Gamble was on June 12, 2022. The couple posed for a picture on a yacht along the Amalfi Coast. He was also present for Khloe’s birthday dinner on June 27 and posted a heartfelt message on Instagram. There is clearly no trouble in paradise.

Time to Slow Down

Although Gamble is 15 years younger than Kris, he knows the importance of relaxation. Since Kris appeared on our TV screens in 2007, she has been working every day. Even her kids have tried to get her to take time off and relax, but she has difficulty stepping away from business.

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Gamble told Kris she needs to slow down to lower her stress levels. He has organized spa days and makes sure to handle other things when she has to juggle many projects. Gamble is always there when she needs him.

Don’t Kiss and Tell

While gossip magazines say their information comes from “a close source,” Kris has strict rules for people who hang out around her family and come into her home. Anyone with real information about Kris and her relationship would never tell because of her strict NDA.

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Kris makes everyone sign a non-disclosure agreement when they come into her home because some people don’t have the best intentions and want to sell stories. She used to have a sign that said, “What we say here, what we see here, let it stay here when we leave here.”

She’s Just Like Us

Kris has been in the spotlight for several years and is worth millions, but that doesn’t mean she doesn’t love a good bargain. She has said many times how much she loves shopping at Costco, the wholesale store. Kris compares shopping there to getting a massage.

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Kris might not be able to go to the store like a regular person, but she does her best to go to Costco every few months. She stocks up her pantry with snacks for her many grandchildren. Kris might be on TV, but she’s just like everyone else.

The 10 Percent Adds Up

As the momager of her six successful children, Kris makes money from their endeavors and her own ventures. As of 2022, Kris is worth a whopping $170 million. She has come a long way from her days as a bored housewife, and now she is a BO$$!

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Kris only started her job as a manager when she was 40 without proper schooling or training. While people think she and her family are rich and famous for no reason, Kris has worked hard to build her empire. No one works harder than Kris Jenner.

Things Haven’t Always Been Easy

While her life seems perfect now, Kris didn’t have an easy childhood. When she was seven, her alcoholic father abandoned the family. Her mother, Mary Jo, was left to raise Kris and her sister Karen on her own. Luckily, she found love again.

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Mary Jo remarried a businessman named Harry, whom Kris considers her father. She didn’t grow up with a lot of money and wanted a better life for herself. Some of her childhood friends said she was after a man with money, but Kris has proven she can stand on her own.

Her Biggest Regret

Kris is now in a happy relationship with Gamble, who adores and respects her. Still, she has one major relationship regret. Kris admitted that one of her biggest regrets was cheating on Kardashian and ruining her marriage. She realized he was the perfect husband only after their divorce.

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When Kardashian passed away from cancer in 2003, she felt guilty that she wasn’t there for him in the end. Kris had a good friendship with him after their divorce and wished she could have called him for advice when she broke up with Jenner.