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From a Popstars contestant to his former personal assistant: Kyle Sandilands' complex love life.

Kyle Sandilands has had a number of high profile relationships, but so far, none have worked out.

He announced his breakup from long-tme girlfriend Imogen Anthony in November 2019, just short of a decade after his divorce from singer Tamara Jaber.

On radio in April, Kyle, who is currently dating his former personal assistant Tegan Kynaston, told his radio co-host Jackie ‘O’ Henderson he self-sabotages his relationships.

Kyle’s reason is actually really self-reflective, but not all breakup excuses… are. Post continues below video.

Video via Mamamia

“That’s what I do. I think I shut down quietly as time goes on,” he said on air during The Kyle & Jackie O Show. “And then you just drift apart, drift in different directions,’ the shock jock admitted.

The confession was in response to a throwback clip recorded in 2007, of Kyle reading out a letter to ex-wife Tamara after she had moved to the United States to further her music career.

“To my beautiful girl, I know I’m not traditionally what people think as romantic, but only you and I know the special bond that we share,” Kyle said at the time.

“You are everything to me baby, and I’d die without you. And when you leave in a few weeks I will cry every night that you’re not with me.”

“I love you and I’m so proud of you my angel. You have changed the way I look at the world, the way I look at life, the way I look at love. And I do truly love you. Love, Kyle.”

Kyle and Tamara met at her audition for season two of Popstars (he was a judge on the show, remember?). They were together for 10 years, and married for two.

kyle sandiland tamara jaber
Kyle and Tamara in 2007. Image: Getty.
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In a 2016 interview with Woman's Day, Tamara spoke fondly of the radio shock jock, despite having once described their two-year marriage as 'miserable'.

"I've never regretted marrying Kyle, not in a million years. I know a lot of people might think I do but I don’t regret it at all," she said.

"People assume he’s a pr*ck but he's kind of sensitive."

On Thursday, Kyle said his tendency to shut down was probably what ended their relationship, as there was "no real fight" that led to the breakup.

"I probably didn't pay much attention to the other half back then. I was younger, I was driven mainly by work and I was like: 'Oh yeah, I've got a girlfriend, got a wife. Ticked that box, move on'," Kyle said.

"We probably never dealt with any issues either because of the non-arguing. She kept things to herself... and you just drift apart."

In 2018, Kyle opened up about his sex addiction following his divorce from Tamara in 2010.

The radio co-host shared live on air that after his marriage breakdown he went through a two-year period of being "so depressed and shocked about it that I didn’t feel like a man".

In conversation with former Labor senator Sam Dastyari, Sandilands reflected on the pain he endured after the two-year marriage ended.

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"Part of the problem was that the sex had dried up and I thought 'okay I'm going to have to pick up my game in this area'.

"I think that part of the reason why I was a sex addict was I wanted to prove to myself I was still a man… and still desired. And I could still desire women and treat them well," he said.

"Plus I was addicted to drugs as well. I wasn't just depressed but I was confused and I was sort of in a weird hole."

kyle sandilands split
Kyle and Imogen. Image: Getty.

In 2011, Kyle began dating model Imogen Anthony after meeting at Kyle’s 40th birthday party.

In 2014, Imogen, a model and designer, told Maxim she knew their relationship was real when Kyle, now 48, told her he loved her after just two weeks.

They had a 20 year age gap, but according to Kyle, age was not a factor they ever worried about.

"I don't see any age difference between us," he said in 2013. "She is not a super-young 22-year-old and I am not a super-old 41-year-old.

"I am a workaholic but I spend every moment I can with Imogen."

Imogen told News.com.au last year their relationship worked so well because she and Kyle are basically "the same person".

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But in November 2019, after weeks of speculation, Kyle confirmed the end of his relationship with Imogen.

"We haven't been living together for a few months, quite a few months, unfortunately, it’s run its course," he said on The Kyle and Jackie O Show at the time.

Imogen also announced the news on Instagram, sharing: "We have a lot to deal with separately... it's been one of the hardest years of our lives, separately. I've got so much family stuff, and you know, there's so much health stuff involved between us, and there's... we just kind of want to... get ourselves into the best form of ourselves that we can be, without kind of pissing in each other's pockets."

Kyle Sandiland Tegan Kynaston
Kyle and Tegan on New Year's Eve. Image: Instagram.

Now Kyle is dating Tegan Kynaston, the communications director of Kyle's company, King Kyle. She was previously his personal assistant.

According to the Daily Telegraph the pair have been together since early December, with Tegan introducing him to her parents at her 34th birthday party.

She also uploaded a photo of her kissing Kyle on the cheek while they were at a New Year’s Eve celebration in Sydney, and in February described him as her 'love' in a caption for a couple selfie.

Feature image: Getty.

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