Kris Jenner and longtime boyfriend Corey Gamble have been seriously dating for over five years now, and since then, Gamble has wiggled his way into the Kardashian circle. The two met in August of 2014 – just a month before she filed for divorce from Caitlyn Jenner – and started dating later that year in October. They have been together ever since – minus a few hiccups here and there.
While Gamble has become more comfortable in the family throughout the years, it wasn’t always an easy road. The 39-year-old former tour manager for Justin Bieber and 64-year-old Jenner share a 25-year age gap, so the momager’s kids initially felt apprehensive about anything longterm. In one episode of Keeping Up With the Kardashians, Gamble acknowledged the age gap. “I like all of y’all, but y’all are girls,” he said. “I’m a dude and I know how that s*** can go. I’m a young dude dating your mom. Y’all are not really my f****** kids. We are technically peers.”
The kids have had their ups and downs with Gamble, he admits he’d like to get closer with Kendall Jenner. “It’s a lot of girls in one group, so it’s hard to be close to everybody,” Gamble says in a confessional in the newest episode of KUWTK on October 8. “I’m not close to Kendall, but if she ever needed me I’d be there.” He adds that he’s looking forward to spending more time with Kendall Jenner on their family vacation to Palm Springs.
Later in the episode of KUWTK, Gamble tells Kylie Jenner. “It’s such a blessing you’re here, because when you’re not here, it’s off,” with the camera panning to Kendall. While on the trip, Kendall and Kylie Jenner get into a major argument.
After all the sisters – minus Kendall Jenner – go out, Gamble has a plan to drive home to LA that night with Kylie and Kendall Jenner. In a separate car, Kourtney Kardashian calls one of the girls to make sure Gamble is with them. But the only thing they hear on the other line is high pitched screaming about who they are dropping off first. “It just sounds really crazy,” Khloe Kardashian says in a confessional.
Gamble and Kylie Jenner drop off Kendall Jenner into the other car, and Kendall Jenner tells her side of the story. After the sisters got into a disagreement about their LA drop-off destination, Kendall Jenner claims that Kylie Jenner slapped her, she slapped her back, and Kylie Jenner put her heel in her neck.
Kendall Jenner also says about Gamble, “This man is wild, he really just said f*** you.” She adds that his comment made her “hysterical,” especially knowing how close Gamble is with her sister. Immediately, all of the older sisters and Kris Jenner know that Gamble’s involvement will take a toll on the family. “Corey’s involvement makes this so much more complicated,” Kourtney Kardashian says in a confessional. “It just really sucks [for her mom].”
Gamble Disagreed with Kourtney Kardashian & Scott Disick’s Parenting
Kourtney Kardashian, Scott Disick, Kim Kardashian, Jonathan Cheban, Kris Jenner, and Corey Gamble all got dinner together on a season 17 episode of KUWTK when things began to implode. Kourtney began explaining how she lost her nanny, because their 8-year-old daughter Penelope scratched the nanny’s face. “P can be out of control,” Kourtney told them. “I think she almost, like, blacks out and does these wild things.”
Gamble immediately responded, saying, “If a kid scratches you, can you pop the kid and it’s cool?” Kim also gave her two cents, telling Kourtney that her daughter North would retaliate against her nanny, too. Gamble didn’t stay quiet for long, and told the parents, “I’m sorry, but if P scratched me for no reason, I’m whipping her a** and I’ll explain to you all later … I would whip her a** if she scratched me.”
Disick then got involved and asked for clarification. “You would whip Penelope’s ass if she scratched you?” he asked. Gamble defended his statement with, “I would give her a spanking for sure.” Kris backed him up on the condition that “if she scratched” him, that’s what he would do.
Disick was outraged, and said, “My daughter. What are you talking about? You would you whip my daughter’s ass if she touched you?” He continued, “A little 6-year-old girl? What the f*** are you talking about? Stop it, stop it, Corey. You are not going to beat my little daughter’s …”
Kim Kardashian then tried to diffuse the situation, also backing Gamble, saying, “I don’t think he’s meaning, like, beat her.” But, Kourtney Kardashian was quick to defend her daughter and back up Disick, by insisting, “Yes, he does mean that. He does mean that.”
Kanye West and Khloe Kardashian Argued with Gamble
After a few years of dating later, Khloe Kardashian and other family members still felt like Gamble was holding back. Kanye West texted Gamble in season 16 of KUWTK. “Something along the lines of, ‘Look, we don’t know you, we’ve never met any of your family members,’” explained Kim Kardashian, as Scott Disick, Kourtney, and Khloe Kardashian met with Kris Jenner. “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,” Kim said.
“Kanye’s delivery wasn’t great, but the essence of what he said is true,” Khloe responded. “Corey does tend to be pretty secretive and that does have me pretty guarded…We don’t know Corey like that.” But Jenner still came to Gamble’s defense. “Nobody really slows down enough to take a look at it from a bird’s eye view of my life,” Jenner told Khloe. “I want you to recognize that when you do question my relationship with Corey, it isn’t okay and it hurts feelings. 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.”
Later on in the episode, Khloe and Kim apologized to Gamble for assuming the worst. “We’re happy you make our mom happy,” Khloe said. “We just want to move forward and be in a good place.”
Gamble and Kylie Jenner Get Along Well
Corey Gamble and Kylie Jenner have both said that they’re super close. “Kylie’s my ace, we always shoot the s***,” Gamble says in a confessional on an episode of KUWTK. “She’s always such a happy and outgoing person.” Gamble adds that out of all the daughters, Kylie Jenner talks to him and checks in on him the most.
Later in the same episode, Kylie Jenner reinforces Gamble’s opinion. “I love Corey,” she says in a confessional. “Corey and I have such a great relationship…He’s good to my mom, and he’s just helped me navigate through life.”
When the family gets ready to go out in Palm Springs that night, Kylie Jenner says that she’s “planning on getting loose.” Kylie Jenner asks Khloe Kardashian and her mom, “Should we take a shot?” When both say no to the shot, Gamble joins in on the fun. Kylie Jenner pours two tequila shots, and Gamble tells Jenner, “I will do whatever we do, this is how we live. We don’t rush. We float through life like unicorns.” Kylie adds to the sentiment, saying, “I’m taking a shot!” Kylie says. “Let me f****** live!”
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