They were once upon a time, one of Hollywood’s most loved and respected couples.

But Kris Jenner and Caitlyn Jenner’s love story was not meant to stand the test of time.

Caitlyn, 71, who previously identified as Bruce Jenner before her transition, is part of the Keeping Up With The Kardashians clan, and ex-husband to the showbiz mogul Kris, 65.

The former lovebirds, who share daughters Kendall, 25, and Kylie, 23, together, tied the knot in 1991 and enjoyed 24 years of marriage before they ultimately decided to officially call it quits on their whirlwind love story in 2015.

As speculation about their crumbling marriage began to dominate headlines, Kris and Caitlyn were forced to officially announce their separation in October 2013.

"We are living separately and we are much happier this way, but we will always have much love and respect for each other," they said in a joint statement to E! News.

"Even though we are separated, we will always remain best friends and, as always, our family will remain our number one priority."

Although they remained on good terms following their separation, Kris officially filed for divorce citing irreconcilable differences in September 2014.

By December of that year, their divorce was finalized.

Then, in April 2015, Caitlyn stunned the world by when she appeared on the now-iconic cover of Vanity Fair following her transition from Bruce.

Following the bombshell revelation, many critics claimed that Caitlyn’s transition was the straw that broke the camel’s back in her marriage with Kris.

Despite endless speculation about her transition being the sole reason for the pair’s marriage breakdown, Caitlyn put the rumours to bed when she revealed the real reason for the demise of her and Kris's love for one another.

Speaking on Rob Lowe's Literally! Podcast, Caitlyn explained that her split from Kris was due to them wanting to pursue different paths, more than anything else.

“After 23 years, Kris and I went our separate directions. My identity was not a big part of us separating. There were so many other bigger issues out there,” the star revealed.

However, Caitlyn admitted that her ‘frustration’ with herself caused her to be ‘a little bit shorter’ with Kris at the end of their marriage.

The split and divorce brought about a sudden new light in their relationship and Caitlyn said: "Then all of a sudden, we didn't have any issues. You know, we just, you know, it was calm."

While the pair remained very close friends following their split, in April 2015, things took a turn for the worst when Caitlyn hit out at Kris in her Vanity Fair reveal.

Caitlyn revealed that she was considering undergoing a full gender transition until she met Kris in the late eighties.

The former Olympian decided to put it on hold and instead, tied the knot with Kris only seven months later.

Caitlyn maintains that Kris knew about her gender dysphoria, and even had seen her dress as a woman several times during their marriage.

Talking about her relationship with Kris, Caitlyn said: “I think in a lot of ways she became less tolerant of me. Then I'd get upset, and the whole relationship kind of fizzled.”

Caitlyn went on to say that the couple’s split was “20 gender and 80 percent was the way I was treated”.

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The harsh words didn’t go down well with Kris, who became visibly upset during an episode of Keeping Up With The Kardashians, where she told daughter Kim Kardashian on the phone: “He can go f**k himself!

“I honestly wish I never met this man. I mean, just f**k you, Bruce,” she cried.

In her tell-all memoir, which was released a year later, the reality TV star told how her lifelong desire to transition to the woman that she knew she was, affected her marriage with Kris.

Caitlyn described the breakdown of her marriage in her memoir as "a toxic combination of her withering anger with me and my defensiveness and generally being at each other's throats, and the kids asking their mother why she yelled at me all the time."

"When Kris and I separated, it wasn't because of trans issues. It was for a million other reasons. Our relationship didn't work anymore and we mutually decided that it was time to split up.”

Kris was not happy with the way she had been portrayed in the book, and claimed that everything Caitlyn said was ‘made up’.

At the time, the mum of five said: "I really tried hard to improve the relationship and spend a little bit of time, thinking maybe there's something here that I'm not seeing.

“I’ve done nothing but open up my home, and my heart, to a person who doesn't give a s**t. So, I'm done."

While Kris and Caitlyn have reconciled on and off since their marriage breakdown, it’s quite clear that their relationship, and even friendship, will never be the same again.

Caitlyn previously talked openly about her increasingly distant relationship with the Kardashians in an emotional episode of Keeping Up With The Kardashians.

“I just really feel like over the last year and a half we certainly have grown apart," she told step-daughter Khloe, 35.

"Day after day, month after month, nobody calls, nobody checks in. Just, 'Hey, how are you doing?' I haven't gotten that phone call from anybody. You can't help but sit there and think, 'OK, 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."

Although her friendship with Kris appears to be incredibly strained, Caitlyn’s relationship with her daughters Kendall and Kylie has remained incredibly strong.

“They have both been so amazing to me and accepted me from the very start. They still call me dad, which I love, but they use pronouns ‘she’ and ‘her’, which means so much to me. It means more than they will ever know.”

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