Jackie O breaks down: ‘I never felt good enough’ (2025)

Jackie “O” Henderson broke down live on-air this morning during a discussion with American author and motivational speaker Gabrielle Bernstein.

Henderson and her co-host Kyle Sandilands welcomed the New York Times best-selling author to The Kyle & Jackie O Show to discuss her speaking tour of Australia. But the conversation got emotional as Henderson was asked about her love life.

“How would you manifest your ideal partner when you don’t have a vision of what they look like? How do you do that?” the radio host asked Bernstein, after admitting she wants to manifest love in her life.

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“I can’t tap into that. But I also have done quite a lot of work on myself, and I didn’t realise that I never felt good enough until I went deep. And then it all came up and it was like a bloody pressure cooker and everything came out. Sometimes I think we have core beliefs that we’re not even aware of,” Jackie confessed.

When Sandilands asked her why she doesn’t think she’s “good enough”, she cried: “I don’t know, I’m working on it. I feel like I’ve been working on it for two and a half years constantly.”

Bernstein reassured Henderson that “everyone is worthy of love”.

“We are in our being and in our presence, we are an energy of love and that is always reflected back to us when we align with it,” the author said.

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Sandilands then told Henderson not to be so hard on herself as she has “dated some donkeys. You’re way better than the donkeys you’ve dated.”

Henderson has been on a journey of self-discovery in recent years, telling the Daily Telegraph in January that she realised she had to learn to love herself first before she could share her life with another person.

“I think the thing was – for years – I was crying out [to be loved],” she told the outlet. “But also realising that I wasn’t loving myself either. And I think that was the biggest realisation.”

The star was married to then co-host Phil O’Neil, aka Ugly Phil, in the 90s and in 2003 she went on the wed British photographer Lee Henderson. They welcomed daughter Kitty, now 14, but split in 2018.

She sparked dating rumours in 2023 when spotted enjoying a glass of wine on the balcony of her eastern suburbs home with 29-year-old tradesman and model Jack Tyerman, but since then, Henderson has been unlucky in love. However, these days she is looking within to “fill that void”.

“It was like I was expecting someone else to fill that void of giving me the love that I wasn’t giving myself, and then when I did start doing that, the peace that came with that, the contentment of not needing it – because I do have wonderful people in my life,” she said.

“I have wonderful women, especially, and I do get a lot of love, but it was me that wasn’t giving myself that love, and that’s where the yearning was coming from, and expecting it from a partner.

“It was cry for help, but I think I was just a little lost, to be honest.”