Kyle Sandilands has had a number of high-profile relationships.

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

Now, the 50-year-old is engaged and expecting a child with his former personal assistant Tegan Kynaston.

Listen to Mia Freedman's interview with Kyle Sandilands on No Filter, where he talks fatherhood and having kids.

Kyle teased on air during his KIIS FMThe Kyle & Jackie O Showon February 14 that he was doing something he'd never done before, then offered an 'audio clue' of a heartbeat.

"I'm having a baby!" he announced, to cheers from his co-workers.

"We are having a baby, can you believe it? We are having a friggin' baby. I couldn't be happier."

The pair learned Tegan was expecting last week, with the baby due in August.

Tegan said Kyle had "been excellent" since they learned the news.

"And he is very emotional about it, very happy, already looking at cribs online," she said."He wants a little bed crown for above the crib."

In December, Kyle told the Daily Mail he had undergone fertility testing and was given the 'all-clear'.

A month later, he told the Daily Telegraph that children were "definitely not off the cards".

"It has never really been on my priority list and I think that is just because I was that kid that dragged around my childhood issues from my parents' divorce and this and that," he explained.

In January, Kyle and Tegan also announced their engagement on air. Kyle shared their proposal story, explaining that lots of things went wrong in the lead up.

The pair were on holiday together in Port Douglas, and Kyle had arranged for Conrad Sewell to fly up and sing their favourite song, 'Life',at the engagement.

But, two days prior to the proposal, the singer tested positive for COVID and had to cancel.

So, Kyle pretended he had to visit a friend's art exhibit and surprised Tegan with an extravagant display of candles, fireworks, and a beautiful dinner to share with her friends, who were waiting at the venue for his proposal.

"I never thought I could be this happy," Kyle said in his proposal, admitting that he shed a few tears over the night.

On air last year, Kyle told his radio co-host Jackie 'O' Henderson he self-sabotages his relationships.

"That's what I do. I think I shut down quietly as time goes on," he said duringThe Kyle & Jackie O Show. "And then you just drift apart, drift in different directions."

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 ofPopstars (he was a judge on the show, remember?). They were together for 10 years, and married for two.

Kyle and Tamara in 2007. Image: Getty.

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 air, 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 eithe