People laughed at first. When news broke in 2014 that Kris Jenner was dating a guy named Corey Gamble who worked in music management and was roughly the same age as her daughter Kim, the internet did what it does best: it got cynical. They called him a "rebound." They called him a "placeholder." Some even suggested he was on the payroll. But here we are, over a decade later, and Corey is still standing in the background of the Kardashian-Jenner empire, usually wearing silk pajamas or a very expensive watch.
What’s wild is how much we underestimated them.
In the world of high-stakes reality TV and billionaire branding, relationships usually have an expiration date. They’re often built for "storylines." Yet, Kris Jenner and Corey Gamble have outlasted almost every other couple in the family’s immediate circle. While the kids were getting divorced, remarried, and embroiled in messy public breakups, Kris and Corey just... stayed. They became the most stable foundation in a house built on shifting sands. It’s actually kind of impressive when you look at the raw timeline.
The Night in Ibiza That Changed Everything
It started in August 2014. Kris was technically still separated from Caitlyn Jenner (then Bruce) and was attending fashion designer Riccardo Tisci's 40th birthday party in Ibiza. That party was legendary. Kanye West was there, Justin Bieber was there, and so was Corey Gamble. At the time, Corey was working with Scooter Braun’s marketing team, specifically helping manage Bieber’s hectic life.
He wasn't some random guy off the street. He was already deep in the industry.
They met, they talked, and by November of that year, he was appearing on Keeping Up with the Kardashians. The transition was jarring for the fans, but even more so for the kids. If you go back and watch the early episodes where Corey is introduced, the tension is thick enough to cut with a Birkin bag. Kourtney, Kim, and Khloé were skeptical. They weren't just being protective; they were confused by the vibe. Corey is quiet. He’s observant. He doesn't have the "I need to be on camera" energy that usually defines people who enter the Kardashian orbit.
Honestly, that’s probably why he’s still there. He doesn't compete with Kris for the spotlight. He just holds her purse while she owns it.
Dealing with the Age Gap and the Haters
Let's address the elephant in the room: the 25-year age gap. In 2026, we’re a bit more used to seeing varied relationship dynamics, but back then, it was the primary talking point. Kris was born in 1955; Corey was born in 1980.
Does it matter?
To the public, it was a scandal. To the family, it was a logistical nightmare. In one particularly famous episode of KUWTK, Kanye West (who was then very much part of the family fold) sent Corey a text basically asking, "We don't know you, where did you come from?" It was blunt. It was rude. But it represented what everyone was thinking. Corey’s response was essentially to stay in his lane and keep showing up.
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He didn't fire back with a press release. He didn't go on a podcast to "clear the air." He just stayed.
There’s a specific kind of maturity required to date a woman like Kris Jenner. You aren't just dating a person; you’re dating a corporation. You’re dating a mother of six, a grandmother to a dozen plus, and a manager who works 20 hours a day. A younger man with an ego would have crumbled under the "Momager" shadow. Corey seems to thrive in it. He’s the person who makes sure she eats, the person who travels with her to Paris Fashion Week, and the person who handles the security details that would give anyone else a migraine.
Why Corey Gamble is the Ultimate "Stabilizer"
If you watch The Kardashians on Hulu now, the dynamic has shifted. Corey is no longer the outsider. He’s the "fun uncle" who also happens to be dating the boss. He’s often seen hanging out with Scott Disick or Travis Barker. He has his own things going on—he's still involved in brand talent management and has a massive network in the music world—but his primary role in the public eye is being Kris’s rock.
Here is the thing people miss: Kris Jenner spends her entire life making decisions for other people. She’s the fixer. When Kylie has a PR crisis or Kim has a legal hurdle, Kris is the first phone call. Who does the fixer call when she is stressed?
That’s Corey.
He’s the "soft landing." We’ve seen glimpses of this in the show—moments where Kris is overwhelmed and Corey is the one telling her to put the phone down. He provides a level of emotional support that isn't about business. It’s about being a partner. It’s quiet. It’s consistent. It’s remarkably normal for a life that is anything but.
The Mystery of the Engagement (or Lack Thereof)
People are obsessed with whether or not they’ll get married. Every time Kris wears a diamond ring on that finger, the tabloids go into a frenzy. But Kris has been very vocal about this. She’s been married twice. She’s done the big weddings. She’s had the legal entanglements.
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She often cites Goldie Hawn and Kurt Russell as the blueprint. If it isn't broken, why involve the lawyers?
At this stage in her life, a marriage contract doesn't offer much that she doesn't already have. She has companionship, loyalty, and a partner who fits into her complicated family puzzle. Adding a marriage license to the mix just seems like extra paperwork for a woman who already signs enough contracts to fill a library.
The Friction Points: Not Everything is Perfect
It hasn't been all sunshine and roses. We have to talk about the friction, because that’s what makes it a real relationship. There was that massive blowout with Kendall Jenner a few years back. Do you remember the "car fight" in Palm Springs?
Kendall and Kylie got into a physical altercation in the back of a car, and Corey was right in the middle of it. Kendall later accused Corey of being "rude" and taking sides. It was one of the few times we saw the mask slip. It showed that being the boyfriend of the matriarch is a tightrope walk. You’re "family," but you’re also "not family" when the blood relatives start fighting.
Corey’s defense was basically that he was trying to handle a chaotic situation. Whether he handled it perfectly is up for debate, but it highlighted the impossible position he occupies. He has to be a father figure, a friend, and a bodyguard all at once, without ever overstepping his bounds. It’s a job no one would envy.
What We Can Learn From Their Longevity
Most people looking for "relationship goals" don't look at Kris and Corey. They look at the flashy, new romances. But there is a lot of tactical wisdom in how they operate.
- Define your own roles. They don't follow a traditional "husband and wife" script. They’ve built a partnership that fits their specific, weird lives.
- Ignore the external timeline. If they had listened to the critics in 2014, they would have broken up within six months. They didn't. They let the relationship breathe.
- Support, don't compete. In a power couple, someone has to be okay with being the "plus one" sometimes. Corey handles that with more grace than most.
The reality is that Kris Jenner and Corey Gamble represent a very modern type of companionship. It’s about utility as much as it is about romance. It’s about finding the person who makes the "business of living" easier.
Moving Forward: The Next Decade
As Kris moves further into her 70s and Corey into his 40s, the dynamic will likely continue to evolve. We’re seeing more of Corey as an individual—his fashion choices, his presence at sporting events, his own business ventures. But the core remains the same. He is the person standing three feet behind the most powerful woman in entertainment, making sure the lights stay on and the drinks stay cold.
If you’re wondering how to apply their "success" to your own life, look at the stability. In a world where everyone is looking for the next best thing, there is immense power in just staying put.
Next Steps for the Curious:
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- Observe the body language: Next time you watch the show, don't listen to the dialogue. Watch how they sit together. There is a genuine comfort there that you can't fake for cameras.
- Audit your own partnership: Are you competing with your partner, or are you their "soft landing"? Sometimes being the support system is the most powerful position in the room.
- Ignore the "rules": If a 25-year age gap works for the most scrutinized family on earth, maybe the "rules" of dating are more flexible than you think.
They’ve proven that longevity is the ultimate "gotcha" to the haters. You don't have to explain yourself if you just outlast everyone else.