Lee Henderson and Gabriella Motta: A Quietly Happy Relationship
Lee Henderson was seen strolling through Sydney’s The Rocks with his girlfriend, Gabriella Motta, over the weekend. While he appeared relaxed and happy, it was the sparkler on her wedding finger that drew attention from onlookers. The former husband of radio icon Jackie O was spotted chatting with his Brazilian jiu-jitsu instructor partner, showing off their affection for each other.

Gabriella was seen wearing what could be an engagement ring on her left hand, sparking speculation about a potential proposal. However, the couple has not officially confirmed anything. Despite this, the news has been circulating among fans and followers, with many eager to know more about their relationship.
If they have indeed taken the next step, it seems the proposal would have been kept very private. A friend of the couple previously shared insights with New Idea, suggesting that any engagement would be a simple and low-key affair.

“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 were married from 2003 to 2018, and they share custody of their now 15-year-old daughter, Kitty. Following their split, the couple has maintained a warm friendship for the sake of their child. If there is a celebration on the horizon for Lee, it’s likely that Jackie will be raising a glass in support.

Lee and Gabriella first became linked in 2018 when they were spotted on a beach date. Since then, the pair has kept their relationship largely out of the spotlight.
The History Between Jackie O and Lee Henderson
Jackie O and Lee Henderson announced their separation in October 2018 after 18 years together, 15 of which were spent married. The split was described as entirely amicable at the time.
“It’s not a decision we took lightly,” Jackie said on air during The Kyle and Jackie O show on KIIS FM. “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. She praised Lee for his unwavering support of her career but acknowledged that 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.

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, she 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.

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