Keeping Up with Khloé Kardashian and Caitlyn Jenner: A Timeline of Their Strained Relationship

Caitlyn Jenner and Khloé Kardashian aren’t on the best of terms.

During a recent episode of the British reality show, I’m a Celebrity … Get Me Out of Here!, Jenner, 70, said she hasn’t “really” spoken to Kardashian, 35, in nearly six years.

While Jenner admitted that their relationship with the Revenge Body star grew strained when she transitioned, the former Olympian said she isn’t quite sure why. “Khloé for some reason was pissed off about something through this whole process. Honestly, it’s been five, six years and I really haven’t talked to her since. I don’t know what it is, and that’s all I can say,” Jenner said on the show, adding that she and her former stepdaugter Kardashian “were really close” in the past.

Caitlyn shares son Burt, 41, and daughter Cassandra, 39, with ex-wife Chrystie Crownover; sons Brandon, 38, and Brody, 36, with ex-wife Linda Thompson; and daughters Kendall, 24, and Kylie, 22, with ex-wife Kris Jenner, who is also mom to Khloé, Kourtney Kardashian, Rob Kardashian and Kim Kardashian West.

Below, a detailed timeline of Kardashian and Jenner’s relationship, from starring in Keeping Up with the Kardashians together to their subsequent rift.

2015

During a 20/20 interview in 2015 with Diane Sawyer, Jenner came out as transgender, and made her public debut as a woman on the cover of Vanity Fair shortly after.

After news of her transition, the Kardashian-Jenner family revealed they were blindsided by the news. “All these tabloids are coming out… we’re like, ‘We could ask the source.’ You’re our dad, we’ll ask you,” Khloé recalled during an appearance on Howard Stern’s SiriusXM radio show in 2016.

The Good American mogul also said her stepparent told the family the reports were untrue, and that their family did not find out about the transition until going to a meeting with E!, when the network mentioned she “was having a TV show about transitioning or something.”

Caitlyn would only talk about the transition to the family on camera at first, according to Khloé, who speculated: “Maybe he felt like we couldn’t get as upset or something.”

In addition, Kardashian told Stern that her family was upset by being kept in the dark. “We felt so like, ‘What the f—? We’ve been asking you and why do business people know?’ ” she said. “I never want someone to feel like they have one-up on our family. We are a family. We’ve never turned our backs on each other yet with all the clusterf—s of s— that’s happened in our lives, why would we now?”

She also said her initial reaction to the news was wanting to ask Jenner to “just stop lying to us about things,” adding, “Just lay it on the table, what are we doing? What’s happening? Even then he didn’t tell us … we didn’t know when he was going to start fully dressing as Caitlyn.”

In the season 12 premiere of Keeping Up with the Kardashians in 2016, Jenner responded to his stepdaughter’s interview with Stern through angry texts. After the conversation, Kardashian called her mother, claiming that she was done with Caitlyn.

2017

Kardashian and Jenner had an intense heart-to-heart conversation during a season 13 episode of Keeping Up with the Kardashians, during which Kardashian revealed she has “a ton of opinions and feelings about Cait. But before Caitlyn, there was Bruce, and Bruce was in my life for like 24 years.”

Over a glass of wine in Kardashian’s home, Jenner admitted: “I just really feel like over the last year and a half we certainly have grown apart. Day after day, after month after month, nobody calls, nobody checks in. Just, ‘Hey, how are you doing?’ You can’t help but sit there and think, ‘Okay, is it because I transitioned? They don’t like me anymore?’ I want to know what I did wrong, what I didn’t do wrong, what I did right, and move forward.”

But at the time, Kardashian said Jenner didn’t think she necessarily “did anything wrong” during her transition.

“‘Cause, I don’t know, if just because you didn’t do something the way maybe I would have preferred that makes it wrong. In this family, we deal with things very quickly. We don’t have time to really process a lot of things because we’re always on to the next,” Kardashian said. “For me, at the time, I just wasn’t at a place in my life where I really could invest in new relationships.”

Kardashian added, “For me, you’re all I remember — Bruce was. So not having you in my life, it’s a huge blow because I’m like okay, my second dad, this guy that I’ve grown up with, that raised me, was taken away from me. No one really let me have that.”

Then, in her book Secrets of My Life, which was released in April 2017, Jenner claims that ex-wife Kris knew more about her gender identity crisis than she’s publicly admitted. The claim caused further tension between Khloé and Caitlyn.

And in a 2017 interview with Good Morning Britain, Caitlyn said she’s proud of the book but “unfortunately, the Kardashians, and particularly Kris, didn’t react that way,” adding, “I went overboard to be nice, to be friendly, to be open, but also tell my story and my side of the story. Since the book came out, I’ve never talked to Kris again. Kim, I haven’t talked to in six, nine months, whatever it is.”

2018

In January 2018, Jenner admitted on ITV’s Piers Morgan’s Life Stories that she “didn’t trust” the Kardashians and chose to keep the last few pages of her memoir from them when she shared advanced copies.

During a February 2018 interview on ITV’s morning show Lorraine, the then-pregnant Kardashian — who welcomed daughter True with ex Tristan Thompson two months later in April 2018 — made it clear that motherhood wouldn’t bring her closer to Jenner.

“No, I don’t think that affects anything with Caitlyn. [Things are] just as they are,” the mom of one said.

2019

Kardashian said she was “fine with Caitlyn” during an episode of Laura Wasser’s Divorce Sucks podcast in May 2019. “I saw Caitlyn recently, trying to think when, but yeah when I see Caitlyn it’s fine. I think we’ve really come a long way. It was a struggle for all of us … not because she was transitioning. I think from just how it was all handled.”

Kardashian continued, “But I also think, when your emotions die down, you’re able to really look at everything and be like, ‘We’re all humans and we’re all trying to figure this out.’ “

However, when sister Kylie set up a dinner for Caitlyn at Nobu in Malibu in October, which she documented on her Instagram Story, Khloé was not there. Instead, she said she had been “shooting a commercial all day.”

During a November episode of I’m a Celebrity… Get Me Out of Here!, Caitlyn spoke with her castmates about living life in the Kardashian-Jenner family’s spotlight and explained that she came out to all of her children first, starting with her son Brandon.

Then the I Am Cait star claimed that her relationship with Khloé, 35, has been strained ever since. “The only one that was really — and I still, even to today, can’t quite figure it out — was Khloé,” she shared. “Khloé for some reason was pissed off about something through this whole process. Honestly, it’s been five, six years and I really haven’t talked to her since.”

Jenner added, “I don’t know what it is, and that’s all I can say. And Khloé and I were really close. I raised Khloé since she was 5 years old. I don’t know what her issues are, I really don’t know.”