His ill-fated marriage to Tamara Jaber and subsequent romance with ex-girlfriend Imogen Anthony are well documented.
And Kyle Sandilands, 52, has now spoken for the first time about a third woman who stole his heart while they worked together in a radio studio early in his career.
During Monday’s episode of The Kyle And Jackie O Show, newsreader Brooklyn Ross told Kyle he was going to meet the woman – who still works in radio – at the ACRA Awards over the weekend.
In an awkward twist, Brooklyn said she had even asked where Kyle was, suggesting she wanted to reconnect with him after almost three decades.
Kyle, who did not attend the ACRA Awards, went on to tell the story of how he had proposed to the woman before things fell apart due to his infidelity.
Kyle Sandilands, 52, (pictured) has spoken for the first time about a woman who stole his heart while they worked together in a radio studio early in his career.
“I was sexually active with seven of the women I worked with and she was the one who rose above the rest,” he admitted.
“You’ve put a ring on it,” co-host Jackie ‘O’ Henderson added.
Kyle admitted the relationship ‘ended in a cloud of hell’ after his wife discovered he was cheating.
During Monday’s Kyle And Jackie O show, Kyle told the story of how he proposed to his wife before things fell apart due to his cheating.
“Oh, you faced (her),” quipped Kyle’s co-host Jackie ‘O’ Henderson (pictured). Adding: ‘Don’t you realize at some stage they’re going to pass the check?’
“Oh, you dealt with that,” Jackie teased, adding: “Don’t you realize at some stage they’re going to pass the check?”
“Well, I never thought of that,” Kyle laughed.
Kyle revealed that he went to extreme measures to escape the embarrassment of his actions.
“I felt so ashamed that I actually left town – as all good people do when they get hit. You bail. You foot it. You move the states”, he admitted
It was after he had moved states that Kyle met Jackie and created what would become Australia’s most successful commercial radio show. (Kyle and Jackie pictured in 2008)
“I felt so ashamed that I actually left town – as all good people do when they get hit. You bail. You foot it. You move the states”, he admitted.
‘She is Greek. You don’t mess with an angry Greek woman,” he laughed, before joking that he had been “on the run” for years.
It was after he had moved states that Kyle met Jackie and created what would become Australia’s most successful commercial radio show.
Kyle married his first wife Tamara Jaber (right) in 2008 before splitting in 2010 after two years of marriage. (Kyle and Tamara are pictured in 2005)
Kyle has enjoyed a number of high-profile romances over the years.
He married his first wife Tamara Jaber in 2008 before splitting in 2010 after two years of marriage.
The couple tied the knot in a lavish ceremony in Sydney with Kyle recently admitting he spent a million dollars on the affair.
Tamara, 40, (right) is currently expecting her first child with fiance Billy Kokkinis (left)
He has since revealed he was ‘permanently damaged’ during his marriage to Tamara, who is currently expecting her first child with fiance Billy Kokkinis.
The radio star recently revealed on air that he was worried after his ex-wife once rated their sex ‘two out of ten’.
“I never recovered emotionally,” the father of one admitted.
After splitting from Tamara, Kyle went on to enjoy a long-term relationship with model Imogen Anthony (right)
While he did not mention Tamara’s name, he did specify the damaging incident that occurred during his first marriage.
After splitting from Tamara, Kyle went on to enjoy a long-term relationship with model Imogen Anthony.
Imogen and Kyle were together for eight years, but he never popped the question to the former model.
Imogen and Kyle were together for eight years, but he never popped the question to the former model
The media titan announced his shock split from the VIP Big Brother star on The Kyle and Jackie O Show in November 2019.
He told listeners the couple had “not lived with each other” for months and their relationship had simply “run its course”.
“We haven’t been with each other for a few months now. “Unfortunately, it has run its course,” he said.
Kyle began dating Tegan Kynaston in 2019 following his split from Imogen. (Kyle and Tegan are pictured in March 2021)
Kyle began dating Tegan Kynaston in 2019 following his split from Imogen.
They went public with their romance on New Year’s Eve that year, when Tegan shared a photo of herself kissing Kyle in front of the Sydney Harbor Bridge.
Two months ago, she denied rumors that she was dating the KIIS FM presenter.
The couple exchanged vows in April this year in front of 130 guests at Swifts, eight months after welcoming their son Otto (right)
The couple announced their engagement in January 2022 in a lavish proposal after Kyle popped the question while on holiday in Port Douglas, Queensland.
A month later, also on Valentine’s Day, Kyle announced live on air that she was expecting their first child together, a boy. Otto was born on August 11.
The couple exchanged vows in April this year in front of 130 guests at Swifts – a late Victorian Gothic Revival property with a price tag of $60 million – in a ceremony believed to have cost the KIIS FM host a million dollars.
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Kyle Sandilands’ secret fiancée revealed… and the shocking reason their relationship fell apart: ‘I felt so ashamed’
