When Sydney radio host Jackie ‘O’ Henderson boarded a flight for a meeting with Hollywood megastar Gwyneth Paltrow 10 years ago, she couldn’t know then it was the beginning of a beautiful collaboration.
At the time Henderson, 48, was married, and after a battle with infertility, had welcomed daughter Catalina ‘Kitty’ Henderson. A dinner in New York City was being auctioned off with Paltrow, 50, to raise money for charity.
“I’d always loved her for a long time and people had always poked fun at me on the air because all I ever did was bring up [Paltrow] in my ‘O News’ stories,” Henderson tells 9Honey Celebrity. “They were like, ‘Please, just stop talking about Gwyneth’.”
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At the time, Henderson was co-hosting The Kyle & Jackie O Show on 2Day FM with Kyle Sandilands ahead of their move to KIIS.
They decided to put the call out for companies to contribute towards winning the prize for Henderson, who would don a boiler suit featuring their logos for the adventure.
It was totally worth it, with Paltrow letting her guard down to discuss marriage, children, being a mother and ensuring Henderson and crew felt “that [they] were her friends.”
That evening lived only in her memory until three months ago, when Henderson and her best friend Gemma O’Neill decided to launch Besties, a collaboration that aims to bring women and their ‘besties’ together for a series of events.
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Their dream guest for their first event was Paltrow, but they didn’t expect it to be so easy.
“We just thought she was the perfect fit for the first one and the fact that we got a response back so quick it threw us,” Henderson admits.
The event will take place in Sydney on October 27 at Aware Super Theatre at the International Convention & Exhibition Centre, with pre-sale tickets up for grabs from today.
“I know she’s going to bring it on the night and that’s why I wanted her to be the first one because I just knew if she’s going to make the effort to come out here she’s definitely going to give you guys a good night,” Henderson says.
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Paltrow is a sometimes divisive figure, owing to the offerings of her lifestyle brand Goop. She famously coined the phrase ‘conscious uncoupling’ when she and Chris Martin divorced in 2016, and Paltrow and her new husband Brad Falchuk didn’t live together for years following their marriage so she could focus on her two children children – daughter Apple, 19, and son Moses, 17.
Henderson says it’s thanks to contributions from the likes of Paltrow that women can “set our own agenda, and this is advice Henderson and O’Neill have come to lean on during their own struggles.
“I’m always amazed at how similar all our stories are. They’re pretty much the same.”
Henderson and O’Neill first met at 2Day FM, with O’Neill serving as the show’s executive producer for a time.
”But I would say the biggest bond for us came when we went through our divorces so that would have been 2019,” Henderson explains. “I mean that was truly a bonding experience because she was going through one as well.”
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Why the years since Jackie ‘O’ Henderson’s divorce are her ‘best years by far’
Henderson has noticed a number of women divorcing in their forties with “similar stories about the kind of marriage they were in.”
“I’m always amazed at how similar all our stories are. They’re pretty much the same,” Henderson says.
“I think it’s just your hit your forties and you kind of know yourself a little bit more and then you start to think about, ‘What is the rest of my life? What am I doing with the rest of my life?’ and so you start to question a lot more I think,” she says.
It has been almost five years since the end of Henderson’s marriage, but she says “these are my best years by far.”
“You probably nurture yourself and surround yourself with people that are good for you and you start to cull things in your life that aren’t serving you well,” Henderson says.
“I think that comes with age, wisdom, knowledge, getting to know yourself, and I think once you get to know yourself a little bit more you just make better choices really. You start to love yourself more.”
Henderson knows how lucky she is in life, having started in radio in Canberra as a teenager and working her way up to one of the top jobs in the business.
“I couldn’t never imagine in my wildest dreams this would happen to me,” she says. “I remember working in Canberra and making a trip into Sydney. I would drive over the Harbour Bridge and think it would be amazing to work in Sydney, but that’ll never happen.”
“I still drive over the Harbour Bridge and always think back to that moment,” Henderson says.
She describes her career as a combination of opportunity and “hard work” as well as a little radio magic in the form of her long and successful career with Sandilands, who was “pretty put out actually” that Henderson didn’t consider him her bestie.
”Kyle’s my bestie but he’s a different kind of bestie,” Henderson explains.
“I still tell him a lot. He knows a lot about my life. We confide in each other a lot. It’s similar but girlfriends are different.”
She is also enjoying her best health in decades, having taken an extended break from work at the end of 2022 to get both her mental and physical health in check following a period of “burn out.”
“I’ll journal, I think journalling is a really good way to find the answers. You’d be surprised at how much you reveal about yourself. You start writing a question and then answering it,” she explains.
Henderson also tries to meditate when she can and also attends therapy “cause I think we all have things in our past that can be blocked for us in life and I think sometimes it’s really good to work through those.”
She is also focused on maintaining her physical health, having recently shed 18 kilograms. Henderson said she made sure to explain to her her daughter that her weight loss effort was “about my overall wellness” and not just how she looked in the mirror.
“I had no energy and I had no motivation,” Henderson says of her health journey.
“It’s probably the healthiest I’ve ever been in terms of my relationship with food, to what it was in my twenties and thirties,” she explains.
“So I do think it clicks and then you keep going and now I don’t even have a desire to eat unhealthy. I naturally want to have fish and vegetables, it’s what my body craves. So I think it’s getting to that point where your mindset is… it’s no longer about dieting, it’s no longer about trying to be ‘good,’ your body just naturally is that way.”
Henderson knows whatever life has in store for her, she always has her circle of friends and her bestie O’Neill to see her through.
“I really am grateful for that in my life. I don’t know what I would have done through those years… they’re so incredibly difficult going through a divorce,” Henderson says.
“I don’t know what I would have done without her.”
Register to see Gwyneth Paltrow at the Besties event in Sydney on October 27 at besties.au, with pre-sales on July 26 from 9am via Ticketek.
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