But some of the most interesting quotes came when the 31-year-old reality star answered Stern’s questions about Caitlyn Jenner, revealing that the family first found out about the former Olympian’s plans to transition in a business meeting for the docu-series I Am Cait.
“We felt betrayed because more business people [knew]," Khloe said. "We felt so, like, what the f***? We've been asking you, and why do [business people] know? I never want someone to feel like they have a one-up on our family. We've never turned our backs on each, with all the cluster f--ks of shit in our lives, so why would we now?”
Even when Caitlyn came clean with her kids, she initially only wanted to talk about it on-camera, “I think for security,” Khloe explained. “He felt we couldn’t get upset or whatever.”
"He did have private talks with us after," she added. "But he never said he was going to transition. He would just say his soul has always been a woman, but I can't tell you if at that moment he really didn't think he was going to transition."
In fact, the family was taken by surprise by Caitlyn’s interview with Diane Sawyer in April, in which she announced her transition.
"Bruce made it a point for all of us to watch it together, and that's when it was the first time we heard a lot of things," Khloe told Stern. "We didn't even know about Diane Sawyer until it was taped and done. On that show is when we genuinely found out about transitioning."
Like her sisters, Kim and Kourtney, Khloe also admitted to childhood memories that hinted at Caitlyn’s struggle with her gender identity.
"When I was a teenager, I want to say like 13, I was in Bruce's closet for some reason, and I pulled a bag down and I found wigs and makeup and all this stuff and I told everyone what I [found]. I don't know why it was alarming to me. I can't remember if there was something else specific. I think I thought maybe Bruce was cheating," she said, adding that her mom, Kris Jenner, and Bruce accused her of making up the discovery. "I don't think they knew what to do—I don't even think my mom knew at the time. But everyone was like, ‘You're making it up.' For some reason this event always stuck in my head, and now all the pieces are coming together."
That secrecy, Khloe said, continued for many years, including through Caitlyn’s transition, which inevitably led to tension within the family.
"We didn't know when he was going to start dressing as Caitlyn and all of that,” she added. “He didn't tell us any of that. I think he knew when, and it was frustrating. So yes, my reaction might have been harsh, but in any normal family, I would like to see your reaction."