A Sydney stroll has got everyone talking.

Lee Henderson looked relaxed and happy on a stroll through Sydney’s The Rocks at the weekend with his girlfriend Gabriella Motta, but it was the sparkler on her wedding finger that caught everyone’s attention.

The former husband of radio queen Jackie O was spotted chatting away with his Brazilian jiu-jitsu instructor partner, the pair looking every bit the loved-up couple.
Could the ring on Gabi’s left hand be a sign of a secret engagement? (Credits: Matrix and Media Mode)
Gabriella, meanwhile, was wearing what could be an engagement ring on her left hand.

The fiercely private pair haven’t confirmed anything, but questions about an engagement are on everyone’s lips.

If they have taken the next step, it sounds like the proposal would have been very much under the radar.

A friend of the couple previously told New Idea that when it happened, their engagement would be a simple, low-key affair.
Lee Henderson and his girlfriend Gabriella Motta. (Credit: Matrix)

“They’re really laid-back people; they wouldn’t have made a fuss and it wouldn’t have been a huge over-the-top event,” the friend explained.

“Probably just at home with the two of them, maybe even with Kitty involved somehow, or at their favourite beach, something like that I’d imagine.”

Lee and Jackie O who were married from 2003 to 2018, share custody of their now 15-year-old daughter Kitty following their split.

The former couple have maintained a warm friendship for Kitty’s sake, so if there is a celebration on the horizon for Lee, no doubt Jackie will be raising a glass.

Lee was first linked to Gabriella back in 2018 when the pair were spotted on a beach date, and the two have kept their relationship largely out of the spotlight ever since.

What happened to Jackie O and Lee Henderson?

Jackie O and Lee Henderson announced their separation in October 2018 after 18 years together, 15 of them married – a split described at the time as entirely amicable.

“It’s not a decision we took lightly,” Jackie said on air during The Kyle and Jackie O show on KIIS FM at the time of the split.

“Lee and I have been so lucky that our separation has been extremely amicable.”

She went on to explain that the pair remained close, speaking on the phone every day and continuing to spend time together as a family for Kitty’s sake.

“It’s not something that happened overnight for us,” she added.

“It’s been a long time. We’ve been separated for a long time. We’re just lucky that we were able to do it in private.”

In her 2024 memoir The Whole Truth, Jackie reflected more candidly on the marriage – praising Lee for his unwavering support of her career, but acknowledging the couple had a habit of avoiding difficult conversations.

“We both got used to living with elephants in every room,” she wrote.

She described their first six months of marriage as happy and aligned, but said the relationship would routinely come crashing down from those highs across their years together.
Jackie, Lee and Kitty in happier times. (Credit: Instagram)

Who is the father of Jackie O’s daughter Kitty?

Jackie and Lee welcomed their daughter Catalina, known as Kitty, in December 2010.

Following their 2018 separation, the pair have continued to co-parent her closely, with Jackie describing Lee as one of her best friends.

Lee has been dating Gabriella Motta since shortly after their split, with the pair first spotted together on a beach date in late 2018.

How many times has Jackie O Henderson been married?

Jackie O has been married and divorced twice.

Before Lee, Jackie was married to radio co-host Phil O’Neill from 1994 to 1999. She was just 19 when they wed, and he was a decade her senior.

The marriage lasted five years before the pair called it quits. Jackie has since described it as feeling like “a high school romance” on the No Filter podcast.

Her second marriage to Lee Henderson lasted considerably longer – 15 years – before they went their separate ways in 2018.