Kourtney Kardashian is laying it all out, childhood drama, clashing with Caitlyn Jenner, and why her experience growing up in the Kardashian-Jenner home was far from picture perfect.
On the May 21 episode of Khloé in Wonderland, hosted by her sister Khloé Kardashian, Kourtney got real about how different her relationship with Caitlyn Jenner was compared to Khloé’s, and it’s clear there’s still some emotional baggage.
While chatting about being a stepmom to Travis Barker’s three kids, Atiana, 26, Landon, 21, and Alabama, 19, Kourtney, 46, was praised by Khloé for being supportive but never overstepping. Khloé pointed out that she respected how Kourtney “knew” her role wasn’t to discipline the kids and said it reminded her of how Caitlyn “did with us so well.” In Khloé’s eyes, Caitlyn handled being a stepdad perfectly, saying, “[Caitlyn] never tried to be Dad, and I always appreciated and respected that.”
But that’s when the conversation took a sharp turn. Kourtney didn’t agree at all. “Okay, so, that wasn’t my experience,” she said honestly. “But maybe that’s why it became your experience. So grateful for that for you.” According to Kourtney, Caitlyn, who was married to Kris Jenner from 1991 to 2013, was nothing like the hands-off figure Khloé described. Instead, she described Caitlyn as “controlling and bossy,” revealing that she would even ban certain friends from coming over to the house when Kourtney was a kid.
Khloé admitted she always assumed Kourtney’s tension with Caitlyn stemmed from the idea that Caitlyn was “replacing Dad,” referring to their late father, Robert Kardashian Sr. But Kourtney corrected that theory fast. It wasn’t about replacing anyone, it was about how she was treated. And what she shared next made that crystal clear.
“I would be like, ‘I want to call my dad,’ and [Caitlyn] would hang up the phone,” Kourtney said bluntly. “We would have yelling wars.” Yeah, full-on shouting matches between stepdad and stepdaughter. That’s a far cry from the peaceful co-parenting vibes Khloé remembered.
It got so bad, Kourtney said she ended up moving in with their dad full-time, which shocked Khloé in the moment. She hadn’t known things had reached that level. For fans, this wasn’t just juicy gossip, it was a rare look into the messy reality behind the perfectly filtered image the Kardashians often show the world.
The episode highlighted just how differently two siblings can experience the same household. While Khloé saw Caitlyn as a respectful parental figure who never tried to take over, Kourtney experienced restrictions, tension, and even being cut off from calling her own father. Her move to live with Robert Kardashian Sr. speaks volumes about how intense those years were.
And the fact that Kourtney is just now sharing all of this shows how long it’s taken to process those memories. It also explains the emotional distance that’s been visible at times between Kourtney and Caitlyn in public and in past Keeping Up With the Kardashians episodes. While Caitlyn has had her own complex journey, including her transition and relationship changes post-divorce, this story from Kourtney adds more texture to how those earlier family dynamics really played out.
Fans can catch new episodes of Khloé in Wonderland every Wednesday at 9 a.m. ET on X and on all other podcast platforms every Thursday. If Kourtney’s honesty in this episode is any hint, there’s a lot more tea coming soon.
