Kyle Sandilands reveals his biggest fear – and why his 50th birthday party might be VERY awkward

Kyle Sandilands has shared some of his secrets in a candid interview. 

Speaking to this week’s Stellar Magazine, the shock jock, 49, revealed that for a long time, his biggest fear was losing his success – and that fear has motivated him. 

‘It was only in the past year or two that I realised hey, that’s an unnecessary fear. But I think it’s maybe part of what’s driven me,’ he told the magazine. 

Having come from an impoverished and difficult upbringing and suffered periods of homelessness, Kyle has always worried that he’ll end up back on the streets. 

‘I’ve rolled the dice and gone sideways with this blind belief that everything will be okay, but in the back of my head my whole plan is not to live in a cardboard box again,’ he added. 

Kyle said that he was ‘fascinated’ with radio and listened in while homeless and sleeping behind a service station, but he never dreamed he’d get to work in the industry. 

‘Once I realised I was there, I had to hang on and I thought if I don’t have this job I’m homeless again. And still, to this day, I do think that in the back of my head,’ he said. 

Elsewhere in the interview, Kyle explained that he’s having a ‘surprise’ party aboard a ‘huge’ boat for his 50th birthday on June 10th – but he is organising much of the festivities himself. 

The KIIS FM star added that it could be quite awkward as he’s inviting a lot of people who don’t like one another. 

‘Some of my family are coming down from Queensland and they haven’t seen each other for 35 years, and some of them don’t get on that well,’ he told the paper. 

Kyle added that his girlfriend Tegan Kynaston, 35, will be coming along, as well his friends and radio staff. 

No word on whether he has invited his ex-girlfriend, Imogen Anthony, 30, but the radio star is known to be friendly with his exes. 

The pair started dating a few months after his split from former girlfriend Imogen in late 2019. 

Kyle had known Tegan for five years before he hired her as communications director for his company in 2017.   

Despite the fact he knew Tegan for several years while he was with Imogen, Kyle made it clear there was no overlap in the relationships.  

He also said Tegan was never his ‘personal assistant’, as was reported at the time.

He told No Filter host Mia Freedman: ‘Once Imogen and I split up [in 2019] there was a bit of time when I was by myself overseas for a while, and Tegan was great.

‘She was someone that had known me well enough and I felt safe talking about anything personal [with her].

‘And she happened to be single, at the same time I happened to be single, and we just admitted to each other – and this was a long time after Imogen and I finished – ‘Oh, there are feelings here.”

Kyle said it was Tegan who broached the subject first, adding: ‘It developed slowly from there. It was nice, it was a nice thing. It came from a real friendship place.’

Kyle was in a relationship with model Imogen for eight years before they called it quits in 2019. He was previously married to singer Tamara Jaber from 2008 to 2010.