‘I had to hit rock bottom’: Jackie O on body image, Kyle Sandilands and finding herself

Jackie O had to hit rock bottom before she changed her life completely. Now in an exclusive interview, she exposes her dramatic weight loss, dating life and what it’s really like working with Kyle Sandilands.

Over the decades, the breezy way in which Jackie “O” Henderson has traded stories with (and sassed back at) Kyle Sandilands has made her a breakfast radio star.

Then she brought her sparkle to TV during a three-season stint as a judge on The Masked Singer.

But in a candid interview with Stellar, she now admits that effervescence was often glossing over her private insecurities, particularly in the wake of a 2020 divorce that sent her into a personal tailspin.

Now, with the help of a bit of tennis – and a lot of support from her 12-year-old daughter Kitty – Henderson is catching up to her confident persona, open to romance and ready for a new adventure.

As she reflects, “Everything about who I usually am had been taken away. Now, it’s back”

Before she took off on an overseas trip to Fiji for the Christmas holidays, Jackie “O” Henderson had never played a game of tennis – let alone picked up a tennis racquet – in her life. Now, five months later, you can find the radio and TV host on the court every day.

Right after she finishes her shift as the co-host of KIIS FM’s The Kyle & Jackie O Show – a breakfast-radio double act that has been ruling Sydney’s airwaves for nearly 23 years – she spends two hours hitting the ball back and forth across the net. And in a nice little metaphor for life, she doesn’t need a partner.

“I do it on my own with a ball machine,” she tells Stellar. “I’m the loser at the tennis court who has no friends. But I can’t get enough of it.”

While it’s too reductive to say that tennis changed Henderson’s life, when asked why – at the age of 48 – she’s assuredly claiming “I’m happier than I’ve ever been”, she again brings up the game.

Jacki “O” Henderson: ‘I’m fitter, healthier and mentally strong. I can’t believe how good I feel this year.’ Picture: Simon Upton for Stellar

“My whole life I’ve been of the mind that you exercise to lose weight,” she explains. “Never had I thought to look into maybe doing a sport that I actually enjoyed.

Why does it take so long for us to work these things out in life? Why am I almost 50 and only realised this now?”

Her untapped love for the sport was but one of many discoveries that has helped Henderson take charge and harness a new-found confidence in the past five months. Take her photo shoot for Stellar, which she says marked a shift in her self-perception.

“When I was in my 20s, I used to do photo shoots all the time,” she says.

“And I remember always hating every photo of myself and never being happy. This is the first time I’ve ever done a photo shoot where I haven’t been critical of myself. I wasn’t worried about my perceived flaws. I wasn’t worried about what my hair looked like. It’s a horrible place to be when you’re really critical of yourself, so it was good to have that feeling. I’m fitter, healthier and mentally strong. I can’t believe how good I feel this year. I’ve had some sort of crazy breakthrough in my life. But I feel like I’ve kind of hit rock bottom to get to this point.”

The gradual descent began in 2020 when she finalised her divorce from her husband of 18 years, photographer Lee Henderson, with whom she shares 12-year-old daughter Kitty.

“You ask anyone who’s going through that and, especially when you have children, it makes it even harder,” she says. “The guilt you feel – and everything associated with that – is very difficult to get through.”

Jackie “O” Henderson: ‘Everything about who I usually am had been taken away. Now, it’s back.’ Pciture: Simon Upton for Stellar

She thought the forced isolation of Covid that followed quickly after would be a good thing. But when the lockdowns lifted, she didn’t lift with them: “Before I knew it, I wasn’t going anywhere. I wasn’t doing anything. I wasn’t eating well. I was drinking too much. Everything about who I am just changed over that time.”

But because the changes were gradual, it ultimately took a best friend’s intervention to force Henderson to hold up a mirror to a life that had become reclusive. Admitting there was a problem was easy. Trying to solve it? Well, that wasn’t. Just as the slide to her personal nadir was slow and steady, so was the climb out.

First, Henderson decided she needed to take an extended time-out from her radio show so she could restore her immune system and move past constantly feeling unwell. Then, of course, there was tennis.

The endorphins she was unleashing by playing encouraged her to engage in more physical activity, and – combined with nutrition advice she had learnt from Weight Watchers (for whom she’s an ambassador) – she started to get her mojo back.

Suddenly, she tells Stellar, “A light bulb switched on in my brain. It was like, ‘What happened to me? Was I in a coma for the past three years?’ I really looked into what I had become as a person and how I’d lost my spirit, my essence. Everything about who I usually am had been taken away. Now, it’s back.”

As she worked to rehabilitate herself mentally and physically, Henderson began to lose weight. At the start of her career, stories about seesawing scales, diet fads and celebrity body quick changes were plastered across the media; today, even bringing up weight loss in a discussion can be fraught.

“I grew up in a generation where I did ballet and I was always told, ‘You can’t eat this and you must diet’,” Henderson recalls. “It was all about what you look like. And I don’t believe that was healthy for the way I look at body image. However, we do know what food and exercise does to our body and how it plays a big part in your mental health. I was 20kg heavier – and while I don’t like talking about weight a lot, 20kg heavier wasn’t healthy for me.”

There’s this fine line between saying, ‘It doesn’t matter what you weigh’ [and] knowing that certain weights affect my energy and motivation and health. I knew I needed to lose weight to feel better, not look better.”

‘I’m not the handbrake in this situation and I’m not the mother in the situation.’ Picture: Simon Upton for Stellar

It’s perhaps no coincidence that just as she’s feeling her best, Henderson’s radio show is also posting its best ratings. Despite being on air for more than two decades, it continues to grow its audience and is the number-one breakfast show in Sydney, as well as being an iHeart podcast and syndicated nationally as a highlights show.

“Last year I would have questioned how long I could do this for,” Henderson admits. “There’s this brain drain that comes with radio and I was struggling with that. But now I feel I could do this job till the day I die. I wouldn’t know what to do without it. It’s a really beautiful outlet to speak to people and cover so many topics, but also laugh and have fun with the people you love.”

Henderson’s relationship with Sandilands is now one of the longest in her life, she says, and, finally, their personal fulfilment is in sync. (Last month, Sandilands wed Tegan Kynaston, with whom he welcomed a son, Otto, last August.)

“Usually what happens is I’ll be happy. I’ll have a baby but he’ll be going through a divorce. Then he’ll be on a cocaine bender for a year or two,” she says of Sandilands’ past drug addiction – which he revealed on the show in 2018; he’s now clean – “and I’m miserable. This is the first year that we’ve experienced both of us probably being at our happiest.”

The fact the two have navigated the cutthroat radio industry (and each other) and continue to thrive, she says, is because their relationship is based on mutual respect and the fact that “I don’t get offended easily. I think that’s what it boils down to. It takes a lot to offend me and I can pretty much laugh off those things so I really do think that’s probably been part of the reason why we’ve managed to keep this relationship going for so long.”

Of course, she’s had a lot of practice handling Sandilands’ unpredictable outbursts. But there are times when the anger following some of his more unsavoury tirades is not only directed at the shock jock himself, with Henderson criticised for failing to pull her co-host into line.

“I do feel that a lot of the time, the women always get the blame,” she muses. “But I’m not the handbrake in this situation and I’m not the mother in the situation. It’s not my job to correct him every time.”

The pair have long been open about their personal successes and foibles on air, but Henderson admits she’s not entirely sure what that will look (or, rather, sound) like now that she’s prepared to date again.

Jackie “O” Henderson stars on the cover of this Sunday’s Stellar. Picture: Simon Upton for Stellar

“Since that separation, I haven’t dated – but now I feel finally ready to date,” she reveals. “And I’ve never really been in the public eye when I’ve dated someone, so… I’ll probably take it as it comes.”

And however that plays out, she shrugs, Kitty remains her priority. She calls their bond her “best relationship” and adds that it rivals the mother and daughter on Gilmore Girls. In June 2022, when Henderson decided to call time on her stint as a judge on The Masked Singer, she explained that “filming always coincides with school holidays and after three years of missing out, I’ve decided to spend my mid-year radio break with my daughter while she’s still happy to hang out with her mum”.

Indeed, Kitty – who accompanied Henderson to Sandilands’ wedding – often comes to the radio station during her school holidays, attends concerts with her mum, and performs side-by-side with her in TikTok videos.

“We’re so similar, for a start,” Henderson says, “so we can really relate to each other. She’s comfortable telling me everything, which I love. And I want to make sure that she always feels comfortable doing that, so I tell her everything I was doing at her age. I don’t pretend that I’m someone I’m not. Yes, I’m a parent and her mum, but I’m also her friend.”

If, as she approaches 50, Henderson has found her happiest self, what does she think the next half-century could hold?

“It’s about continuing to nurture the relationships I do have, and getting out there and saying yes to new adventures,” she says. “I really am open to trying and doing anything. And I think there’s room now to bring someone into my life. I don’t need it, [but] it would be nice to be open to it.”

For more exclusive interviews from Stellar, listen to the podcast, Something To Talk About, below or wherever you listen to podcasts.

Originally published as ‘I had to hit rock bottom’: Jackie O on body image, Kyle Sandilands and finding herself