I can safely say this was not on my 2025 bingo card.
Oprah Winfrey, one of the richest, most powerful women on the planet, instructing her convoy of sleek black limousines to pull over at a tiny Sydney jet base so she could greet… all four of us who showed up.
Yes. Four.
And I was one of them.
There we were, loitering like hopeful competition winners.
I’d even roped in a mate to hold up an extremely unplanned sign I begged him to write in the car. It read, ‘Oprah plz buy me a car’.Â
Oprah Winfrey (left), one of the richest, most powerful women on the planet, instructing her convoy of sleek black limousines to pull over at a tiny Sydney jet base so she could greet… all four of us who showed up
To be fair, subtlety has never been my strength.
When the door of her jet finally opened, Oprah emerged in the kind of travel outfit reserved for powerful women who do not know the meaning of economy class.
She wore loose grey loungewear, oversized sunnies and a chic sand coloured wide brimmed hat. Effortless. Untouchable. Oprah.
We waved. She waved back. Then, in a twist none of us were expecting, she actually pointed at her drivers and told them to stop the cars.
She read it. Paused. Smiled.
‘Buy you a car,’ she laughed. ‘I don’t think I can do that today.’
It was the same energy as a parent saying no to a kid begging for a pony at Westfield. But honestly, I would have settled for a Kia Picanto.
Oprah then delivered the line that will live rent free in my head forever: ‘You get a selfie… but not a car’ as she stepped out of the van to greet us.
‘Buy you a car,’ she laughed. ‘I don’t think I can do that today’
What surprised me most was her team of private security.Â
In the past, you would barely get within ten metres of her.
Yet instead of shooing us away, they were oddly gentle, almost protective of the moment.
One leaned in and said, ‘She’s just come off a flight, give her a little space. She loves her fans.’ It set the tone instantly. Calm. Warm. Human.
This marks her first Australian visit in 10 years, touching down ahead of her Australia and New Zealand speaking series, Oprah In Conversation: Presented by Lilly, hosted by Melissa Doyle.
It promises a deeper look at the woman who built an empire out of empathy and conversation, fronting one of the most watched talk shows in US history before expanding into film, publishing and streaming.
Her last Sydney trip in 2015 was a whirlwind arena tour where she swept in like visiting royalty. Security everywhere. Controlled chaos.
A woman in a league of her own.Â
At 71, she remains one of the most influential people in the world, yet for those few minutes she felt genuinely grounded and present.
She did not buy me a car. But she did something far more unexpected.
She stopped the limo, softened the security, smiled at my cardboard madness and made one of the most powerful women alive feel wonderfully, unexpectedly relatable.
And yes, I got the selfie. Still no Pontiac.
