Strange Things About Kris Jenner And Corey Gamble's Relationship

Kris Jenner is many things: a mother, an epic momager, an avid martini drinker, and the matriarch of the billion-dollar empire that is the Kardashian family. With Jenner's role juggling her kids' bustling careers, it's understandable why Jenner is often seen with a stiff olive-topped drink in her hand on "Keeping Up With The Kardashians." Ever since her family's infamous reality series "Keeping Up With The Kardashians" debuted nearly two decades ago, the personal lives of her and her six children have become a pop culture phenomenon. Sex tapes, illicit affairs, pop culture bombshells, divorces, marriages, and many grandchildren later, the lives of the Kardashian-Jenner clan continue to dominate the news cycle.

Without Jenner, none of the immense success the Kardashians have achieved would have been possible — so much so that she even trademarked the phrase 'momager.' Because of her place at the center of the madness, Jenner's romantic relationships have long been scrutinized. After her first marriage to the late Robert Kardashian ended in divorce and her second marriage with Caitlyn Jenner followed suit, the "Kardashians" star found love again with Corey Gamble. 

While the pair have been together for nearly a decade, many fans (and her own children) have often criticized the talent manager as being less than transparent about his own life. Gamble may have taken a gamble of his own by involving himself with someone over two decades his senior — not to mention the head of one of America's most famous families. We're breaking down all the strange things about Kris Jenner and Corey Gamble's relationship.

They say age is just a number, right? Perhaps that's what Kris Jenner thought when she got involved with someone 25 years her junior. Jenner and Corey Gamble met in 2014 when Jenner's split from Caitlyn Jenner had yet to be finalized, and the couple went public with the romance the following year. Gamble is just two years younger than Jenner's oldest child Kourtney Kardashian, making for what some perceive to be a pretty strange relationship dynamic. 

Despite their large age difference, the two have continued to remain a united front with each other — and for the world of viewers watching. Gamble and Jenner have a lot in common, given the fact that he has worked as a talent agent for several A-listers and was even the road manager for Justin Bieber. 

Haters are gonna hate, however, and Gamble has been upfront about the criticism surrounding the years between him and his long-time girlfriend. He even addressed it on an episode of "KUWTK." In Season 14 Episode 14, the manager admitted: "I'm a young dude dating your mom. Y'all are not really my f**king kids. We are technically peers." Despite the age gap, Jenner gushed about her boyfriend to the WSJ, saying: "'He really gives me a lot of strength and insight. He's a great sounding board. And he loves my kids and my mom, and they love him."

Corey Gamble's past may have come back to haunt him. Before dating Kris Jenner, the talent manager was romantically linked to "Atlanta Exes" star Sheree Buchanan. The pair dated for three years beginning in 2007, but their split was less than amicable. While not much is known about the pair's relationship history, Buchanan filed a restraining order against Gamble in 2010 following the split. 

According to documents obtained by InTouch Weekly, the reality star accused Gamble of following her, repeatedly calling her, and texting her non-stop. Buchanan also alleged he left her with bruises after she said he grabbed her. "He would just show up at my house and come inside. I had to change my locks because he'd managed to somehow get a key," she told the publication. The reality star also questioned Gamble's intentions with Jenner, saying: "I know Corey. He's all about power and money and will do whatever it takes to get it," adding, "He sees the Kardashians as media's first family."

Despite the accusations, the "KUWTK" star came to her boyfriend's defense. An inside source told TMZ that Jenner considers Gamble "a background guy" who would never exploit others for fame. According to the source, the momager "knows stalkers since she and her family have had more than their share ... and Corey doesn't fit the profile." The insider also claimed that Gamble believes "the only reason it's coming up now is because she wanted to make a quick buck from the tabloids."

With Kris Jenner meeting Corey Gamble in the midst of her highly publicized divorce from Caitlyn Jenner, many viewers questioned their relationship. After 22 years together, Kris and her ex Caitlyn announced their separation in 2013 in a shocking split that was only heightened when Caitlyn came out as transgender in 2015. On the heels of the split, the matriarch's children questioned whether or not their mother was rushing into another relationship. 

When the talent manager made his debut on "KUWTK" in 2015, Kim Kardashian was quick to speak on the relationship. "I'm worried about Mom a little bit. She doesn't listen to me when I'm like, 'You know, you should really take it slow' ... I just hope that my mom really thinks things through because I don't want her to rush into anything," she admitted, per People. Khloé Kardashian also had her reservations about Gamble, questioning him as to why he was acting standoffish in a "KUWTK" episode. "I try to give you a hug but I'm always like, I don't know if you want to hug me, I don't know what this is," she admitted, to which Gamble suggested she and Kourtney should "get to know my personality, we'd probably be cooler."

Despite her daughter's doubts, Jenner came to Gamble's defense. "I can't do anything without getting criticized," she admitted on "KUWTK." "It's uncomfortable. It's like everybody wants answers, everybody wants to know what the title is. It's like you're a bunch of haters ... "

Getting the stamp of approval from her daughters over her relationship wasn't immediate for Kris Jenner. During Season 16 of "KUWTK," controversy brewed over how little Jenner's family members knew about Corey Gamble. Kanye West decided to break the ice by sending a questionable text to the talent agent, asking him why he had never opened up about his own family. "Kanye texts Corey something along the lines of, 'Look, we don't know you, we've never met any of your family members,'" Kim Kardashian explained in the episode (per People). "Of course, we've all felt that way and thought that, but for Kanye to just so bluntly say that to him — I feel like that was the wrong choice to make at that time."

Khloé seconded that notion, admitting: "Kanye's delivery wasn't great, but the essence of what he said is true," adding, "Corey does tend to be pretty secretive and that does have me pretty guarded. ... We don't know Corey like that." The Good American founder also revealed she had no idea that her mother and Gamble's relationship would continue to last as long as it had.

The mother of six defended her beau, however, causing Khloé and Kim to ultimately apologize to Gamble. "I want you to recognize that when you do question my relationship with Corey, it isn't okay and it hurts feelings," Jenner told her daughters. "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."

Don't expect Corey Gamble to embark on an acting career anytime soon, especially if Kris Jenner has her way about it. During the Season 4 premiere of "Kardashians" on Hulu, (per E! News) Jenner admitted she made her boyfriend turn down a major television role. The mother of six revealed that Gamble had been offered a role in the popular drama "Yellowstone" but she wasn't up for supporting the venture.

"I'm so excited to watch the next episode of 'Yellowstone,'" Jenner mentioned to Kim Kardashian and Khloe Kardashian while vacationing in Cabo. Gamble then chimed in, jokingly saying, "If it wasn't for you, I would be a 'Yellowstone' star." The reality star explained to her daughters that she made Gamble turn down the role. "I told him to say no," she revealed, "because I thought he was going to have to have a romantic relationship."

If the tables were turned, however, Jenner would happily oblige to star in the series. "Okay, but if they said they wanted you to star and kiss with Kevin Costner," questioned Khloé, "I'm sure you would take it." Jenner then replied: "Oh, that's a hard yes." Kim then suggested Gamble exercise his acting chops in a more intimate form: "Now you know your next role-play: Kevin Costner," the SKIMS founder jokingly suggested. In terms of TV, though, it looks like we won't be seeing the likes of Gamble in a cowboy hat after all! Bummer.

There are some things better left unsaid, especially when it comes to the sex life of one's parents. Kris Jenner's children certainly thought so when they got an unwarranted earful on the momager's intimacy with Corey Gamble. Kim Kardashian aired her grievances while living with Jenner in 2015, admitting on an episode of "KUWTK" (as recapped by People) that she overheard the couple having sex, complaining about the noise. 

But it's not only Kim who bears the brunt of her mother's escapades. Jenner opened up to Khloé Kardashian (much to her daughter's dismay) shortly after she went public with Gamble, telling the Good American founder: "I literally probably have too much sex. I'm exhausted." Years later, the duo was still going strong when Jenner told her friend, Faye Resnick, "I'm always in the mood ... Corey is like a walking, talking Luther Vandross song. He is so sexy always and all I want to do is like, cue the music," she revealed.

Gamble and Jenner even joked about their wild moments while enjoying a date night in Los Angeles. On an episode of "Kardashians", the businesswoman discussed double entendres with her man, saying (via The Sun), "Remember that drink, sex on the beach? And you could walk up to somebody and go, 'Do you want a sex on the beach? Do you wanna try a sex on the beach? We can have the drink or the real deal.'" Gamble then recalled: "We did that ... well, not at this beach but we did it in the Maldives."

They say that the third time's the charm, but when it comes to Kris Jenner and marriage — that might not be the case. The "Kardashians" star doesn't believe tying the knot is in the cards, even after nearly a decade with Corey Gamble by her side. After being pressed by Ellen DeGeneres about walking down the aisle for a third time, Jenner admitted on "The Ellen Show" that sometimes the grass isn't always greener. 

"You know, I've done that twice and it didn't work out so well," the manager joked. "So, I don't know. You never know. As long as things are going so well, then why ruffle it up?" she questioned. Despite her claims, Jenner posted a photo of an enormous diamond on her ring finger to her Instagram story in 2023, leading fans to question whether or not she had changed tunes. A source denied the speculation, however, telling Daily Mail that Jenner has always had the ring in her collection. "Kris is not engaged to Corey, and she has no plans to be," the insider revealed. 

A second source doubled down, admitting: "Kris does not want to put anything on paper regarding their relationship because she knows that, if their relationship does end, God forbid, it would not end well if they were married." With Jenner reportedly being nearly $200 million richer than her boyfriend, one thing's for sure: if these two ever do get hitched, one word comes to mind ... prenup.

The Kardashians are no stranger to cheating scandals. So much so that we've lost count of how many times Tristan Thompson has cheated on Khloé Kardashian. Kris Jenner and Corey Gamble weathered their own controversy over infidelity in 2022 when a since-removed video surfaced on X, formerly known as Twitter. The video recovered via Us Weekly appears to show what looks to be Gamble making out with an unidentified woman at a club. However, the dark clip makes it hard to make out details. 

An insider denied the allegations, telling the publication that "this is a false narrative about Corey." Another source claimed that the talent manager was in Los Angeles watching the Super Bowl at the time, and the video was reportedly taken in Miami. It didn't stop Kanye West from piping up about the rumors in the midst of his beef with his ex-wife Kim Kardashian and her then-boyfriend Pete Davidson. He took to Instagram in a since-removed post to put Gamble on blast, retweeting a screenshot from Hollywood Unlocked, the outlet that broke the story on the controversial video. "We outsiiiiide DONDA 2 2 22 22," he wrote in his post alongside several shocked-face emojis. 

Hollywood Unlocked has since removed the video clip that fans alleged to be the talent manager, and Jenner and Gamble remained tight-lipped about the matter.

Corey Gamble learned the hard way never to get involved in a fight between sisters. During a Season 18 episode of "KUWTK," recapped by BuzzFeed News, tensions reached a high when Kylie and Kendall Jenner were at each others' throats during a trip to Palm Springs. The drama peaked when the Kylie Cosmetics founder refused to drop her sister off at her apartment, leading to a physical fight between the pair. While viewers didn't see footage of the actual violence, they did see Kim Kardashian calling in security to break up the spat. 

Gamble attempted to settle the disagreement, but Kendall screamed: "Corey, I'm not getting in a f**king random SUV by myself!" The talent agent reportedly cursed out the model, telling Kourtney, "This man is wild! He really just said 'F**k you' to me." After returning from the dramatic vacay, Gamble and Kendall re-hashed what went down, with the latter upset that her mother's boyfriend hadn't apologized. "You're 100% in the fight," she told him. "You said 'F**k you' to my face. You can't even say 'I'm sorry.'"

Gamble wasn't feeling remorseful, however, telling her: "Kendall, you've been a rude person for years, man. You're an a**hole when you feel like it. You get riled up for no reason." Two seasons later, the two finally got to a better place. On an episode of their Hulu series "Kardashians," Kendall revealed she finally reached a truce with Gamble on a separate trip to Cabo San Lucas, saying they got the chance to "slow down and actually spend some time together."

Kanye West is notorious for his social media rants, and unfortunately for Corey Gamble, Kris Jenner's boyfriend became just another target. In 2022 the "Jesus Walks" rapper made his opinion about Gamble known when he took to Instagram (per PageSix) to call out the talent manager. "God has a plan to remove the godless Corey needed to never be here anyway," he shared before soon deleting the post. 

He went on to drag Gamble while praising his former mother-in-law Kris Jenner. "He once told my wife he knew what music she should be listening to So when I seen him a week later I had him removed from my daughter's birthday party," he said, adding, "I love Kris This woman is a hero and she's done what she's had to do to protect her family and make sure they prosper even if it meant telling everyone not to listen to me." West went on to post a screenshot of a text that Kim Kardashian allegedly sent him in which Jenner pleaded with the rapper "to please stop mentioning my name. I'm almost 67 years old and I don't always feel great and this stresses me to no end."

Ye also attacked Gamble's career, alleging that he stole music from a producer. The rapper posted a screenshot from a text chain with Rodney Jerkins that read: " ... Corey Gamble stole from me as well! Stole all my MPC zips to give to some lil producer dude he was managing back in the day! I'm glad Kris woke up!" Gamble didn't comment on the accusations. 

A resurfaced video of Kylie Jenner with Corey Gamble and friends at a concert had fans questioning the beauty mogul's dance moves. In the clip posted by The Sun, the Kylie Cosmetics founder seemingly grinds on the talent manager in a black leather bodysuit while her friend records the moment. Jenner received backlash from viewers over the controversial clip, with many commenting that she might have been too close for comfort. "Everything this family does is hyper-sexualized and incest-like. It's extremely disturbing the way the sisters grope each other any chance they get," one Reddit user wrote. Another quipped in the same thread: "Corey creeps me out." 

Gamble and Kylie Jenner have always had a close relationship, with the makeup mogul previously admitting on a "KUWTK" episode (per Life&Style): "I love Corey. I think that he's just an amazing person, I think he treats my mom amazing ... And he's just helped me navigate through life and I really appreciate his advice. He's just always been a good, good guy." Good guy or not, those dance moves may have been better un-shared.