The couple had always been unconventional, and Kyle had declared his affection for the glamour model just two weeks after they met at his 40th birthday party in 2011.
And they've been inseparable ever since.
In an interview with Maxim three years after they first met, Imogen revealed that Kyle had declared his love for her just two weeks into their relationship.
"If anything happened to her, I could never be with anyone else," Kyle told WHO magazine in 2013.
The couple soon moved in together into a $2.5 million mansion in Sydney's Dover Heights, opposite nightclub owner John Ibrahim.
However, despite bonding over their shared love of partying and animals, their relationship was far from perfect.
John Ibrahim, who has been a pal of Kyle's for years, once recalled the couple's first ever fight during an appearance on KIIS FM in 2017.
He said he saw Imogen leap onto Kyle's car "like a cat" in order to stop him leaving their home after an argument.
"I hear the garage door opening and I see Kyle reversing his big a** Bentley out the driveway," he said.
"All of a sudden you see Imogen jump on the bonnet, like you would a cat, with Ugg boots on and a singlet.
"Imogen was screaming, 'Where you going, you fat C-word?'"
He added: "She stood up on the bonnet with her arms folded, and you see him drive back into the driveway the garage door comes closing down. I almost died!"
"I rang [Kyle], and I couldn't talk I was laughing so hard. And he said, 'Don't tell me you saw that?' He said, 'She weighs 45 kilos but I'm petrified of her!'"
In 2018 the couple tried to create a more wholesome image when they purchased a $3 million hobby farm in Robertson, in the NSW Southern Highlands.
They even tried to escape the limelight and both insisted their relationship was based on quiet nights in.
"Social media has a perception of showing you what you want to see. But for us there is a lot of sitting around doing f**king nothing," Imogen said last year.
"We have quiet nights all the time… that's all we do is quiet nights, like sitting in front of Netflix where we have shows we watch constantly."
However, around this time, she also remarked on their "odd kind of love" on Instagram.
"You got that odd kinda love that I like. Eight years, still counting and they are still trying to rock this b***h. Come ON! Get it together people," she wrote.
In August, the pair moved into a rented home in Sydney's Hunters Hill, however it seemed the writing was already on the wall for their relationship, as a neighbour told Daily Mail Australia this week they had "barely seen" Imogen at the property in months.