It's been almost four years since Kris Jenner, 62, and Corey Gamble, 37, were caught getting cozy with each other for the first time. Since then, Corey has become a regular on KUWTK — but it appears as though all that is about to end, as Radar Online reported that Corey is "miserable" still tied to the fierce momager.

The source shared he was seen at the LA restaurant, Delilah, with a group of friends but barely engaged in conversation and texted Kris the entire night. "He was sat with a huge group of people but barely spoke with any of them, unless someone directly came over to the table to say hello and shake his hand."

kris split

It wasn't just this particular group of friends Corey acted uninterested with, either. The source continued, "He was away from them all with his head down on his phone for hours, and later switched tables and did the same thing with another group of people. Corey looked lost and absolutely miserable all night."

While it was obvious to onlookers that Corey wasn't in the best mood, the insider explained he has gotten so used to living a privileged lifestyle with the Kardashian/Jenner gang, that when they aren't around — or Kris just needs some time apart — he's completely lost. "He's a naturally shy guy and although he's trying to throw himself into the clubbing scene while Kris decides what she wants, it's clearly not working for him."

kris corey split

This isn't the first time Corey and Kris have reportedly been on the outs. The Keeping Up With the Kardashians matriarch was rumored to have dumped Corey for Nigerian oil heir and billionaire, Christopher Cunningham, back in October 2017. At the time, a source exclusively told In Touch, "Kris is ready to call it quits with Corey. You can hear it in her voice that she is done."