Kris Jenner and Caitlyn Jenner’s Ups and Downs Through the Years

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Kris Jenner and Caitlyn Jenner's Ups and Downs Through the Years

The way it was. After 22 years of marriage and raising a blended family together, Kris Jenner and Caitlyn Jenner announced their separation two years before the former Olympian publicly came out as transgender.

“We are living apart," the Safely founder previously revealed to Us Weekly in October 2013. "But there is no animosity. We are united and committed to our family. We ended a marriage, but that's not the end of our friendship. I will always love him, but we are no longer a couple in that way. We are happier this way.”

Following their December 2014 divorce, the I Am Cait star publicly announced her transition in 2015 as her relationship with the Jenner Communications founder and their youngest daughters (Kendall and Kylie Jenner) hit a snag. During a February 2016 episode of Keeping Up With the Kardashians, things got heated after the supermodel disinvited the former track star to her debut Victoria’s Secret fashion show.

"Hi dad," the 818 Tequila founder said during a phone conversation during the episode. "I'm very mad at you about something, so ... did you publicly, like, did you have your publicist announce that you were going? Because I don't know how everyone knows and now it's a huge story and I'm actually pissed at you.”

She added at the time, “OK, well I don't want you to go. … You’re gonna take the biggest night of my life and take it away from me? Thank you. No! You can't! You can come to the f--king after-party, you can't come!”

Following the father-daughter pair’s disagreement, Kendall revealed during a confessional that she didn’t want her family’s presence to take away her excitement over this career milestone though Kris was already set to attend the runway show.

Over the years, the former couple’s relationship has gone through public highs and lows as they’ve navigated their post-split new normal.

“From my standpoint, our relationship is not as good as it should be,” Caitlyn said during a November 2021 episode of Australia’s Big Brother VIP. “I don’t have any hard feelings towards her. We did a great job and this and that. Yeah, I wish it was closer, but it’s not.”

While the Olympic medalist admitted that their distance might be due to “misgivings” on Kris’ part, Caitlyn speculated, “I think that’s an understatement.”

However, things seemed to turn a corner during Christmas of that year after the New York native publicly thanked her ex-wife — who’s been dating boyfriend Corey Gamble since 2015 — for a set of wine glasses.

“Wow! Thanks @krisjennner and @coreygamble Merry Christmas,” Caitlyn captioned an Instagram Story snap in December 2021, while lounging in pink pajamas next to her present.

Scroll below to relive the pair’s rocky relationship over the years:

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April 1991

After five months of dating, the pair tied the knot just one month after Kris finalized her divorce from Robert Kardashian.

Credit: Courtesy of Kendall Jenner/Instagram

November 1995

Kris — who shared children Kourtney, Kim, Khloé and Rob Kardashian with the late attorney — welcomed her first child, Kendall Jenner, with the Olympian four years after their nuptials. (Caitlyn, for her part, shares sons Brody and Brandon with ex-wife Linda Thompson and children Cassandra and Burt with ex-wife Chrystie Scott.)

Credit: Courtesty of Caitlyn Jenner/Instagram

August 1997

Two years later, the Kardashian-Jenner brood expanded once more after the former couple welcomed the Kylie Cosmetics founder.

Credit: ABC

October 2007

The family chronicled their over-the-top lifestyle on E!’s Keeping Up With the Kardashians as Kris and Caitlyn balanced raising a large, blended family with their relationship.

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August 2011

To celebrate their 20th anniversary together, the exes renewed their wedding vows during an April 2011 family vacation in Bora Bora. The nuptials were filmed for an episode of KUWTK.

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October 2013

Two years after their televised vow renewal, the pair announced their separation, noting that they had been living apart. While Kris continued living in Calabasas, California, Caitlyn relocated to Malibu.

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February 2016

Upon Caitlyn’s transition, she confirmed that Kris previously knew about her coming out journey.

 “The rules with Kris and I — don’t dress up, certainly around the house. If you really need to do that, when you’re on the road, take stuff and do that. So, I did that for years,” Caitlyn recalled during the Makers Conference in February 2016.

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April 2017

After their breakup, the Secrets of My Life author gushed about Kris, who furnished her new Malibu residence.

 “The day we took it, on June 1 at 8 a.m., she said I could not come over until that night. I came over and the completely empty house was fully furnished, every TV was working,” Caitlyn revealed during an April 2017 conversation at NYC’s 92nd Street Y. “She’s so well organized. I give her a lot of credit. The dryer even worked. She bought all new stuff. She has very good taste. She worked a deal with Restoration Hardware. It was a very nice thought of hers. I appreciate that.”

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November 2019

While Caitlyn’s mom, Esther Jenner, made headlines after dissing the Kardashians’ reality TV show, a rep for the athlete previously revealed that Caitlyn didn’t feel the same way.

“Caitlyn’s team adamantly denies her mother’s statements as they do not represent Caitlyn’s sentiments or feelings towards the show or Kris Jenner,” a statement read at the time. “Caitlyn has time and time again said that the show is the best thing that has happened to their family, and is on great terms with Kris. Her team was shocked — and never consulted — to hear of Esther speaking to press.”

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December 2019

“When Kris and I separated, it wasn’t because of trans issues. It was for a million other reasons,” Caitlyn told the Daily Mail about the dissolution of their marriage. “Kris and I had a great relationship for a long time. We built an amazing family, but circumstances and people change. And I think the hardest thing is to be able to make those changes together and still be as strong. Our relationship didn’t work anymore and we mutually decided that it was time to split up. There was no animosity.”

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September 2020

The Life of Kylie alum later revealed that her transition wasn’t “a big part” of her split from the momager during an appearance on Rob Lowe’s “Literally” podcast, recalling, “There was so many other bigger issues out there. … Then all of a sudden, we didn’t have any issues. You know, we just, you know, it was calm.”

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April 2021

During the final season of KUWTK, Kris helped her ex with career advice amid the coronavirus pandemic after expressing concern about staying in touch with Caitlyn considering their troubled relationship.

“I think my mom is just super traumatized [inside] and that’s OK,” Kim explained during a confessional during the episode. “Her experience is her experience and we all have to be there for her and there’s no time limit that can be put on her for her to feel completely comfortable again.”

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November 2021

“Our relationship is OK,” the Big Brother VIP alum said about their bond during a 2021 episode of the Australia competition. “I think it could be better just because of the kids. It's always the way when you have that. It's all about how the mother and father, how they get along together. Is it easy? Is it good? Do they see each other? Is there any tension?”

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April 2022

“We’re fine. We’re friends, I see her when she’s at a family thing," Kris said about her current relationship with Caitlyn during an interview with ABC News. "It’s, you know, settled down a lot." The manager added that she was initially taken aback by her ex's transition, which caused many of their issues: "It’s a subject that I never thought I’d have to directly deal with, confront, be understanding about something I didn’t understand."

Credit: Courtesy of Kim Kardashian/Instagram

November 2022

During Kris’ family Thanksgiving feast, portraits were painted in honor of all her children, grandchildren, in-laws and boyfriend Gamble. A regal rendering of Caitlyn was also included in the display.