It looks like Jackie ‘O’ Henderson is off the market again.
After two failed marriages and a fling with a ‘toyboy tradie’ that went nowhere, we pictured the 50-year-old KIIS FM breakfast host locking lips with a new man on the balcony of her Clovelly home on Sunday afternoon.
The Daily Mail can exclusively reveal the man making Jackie smile again is Richard Ryan – a pilot and DJ who has been described to us as a ‘big name in the eastern suburbs’.
In our photos, Richard looked to be sporting a black eye – possibly the result of a sports injury – but that didn’t dampen his spirits as he packed on the PDA with the multimillionaire radio star.
He kept things casual in a black T-shirt, cap and shades, while mother-of-one Jackie opted for a white tee and jeans.
Our photographer spied the pair chatting in the sun for several minutes, with Jackie seen leaning for a kiss at one stage with a huge smile across her dial.
It looks like Jackie ‘O’ Henderson is off the market again
After two failed marriages and a fling that went nowhere, we pictured the 50-year-old KIIS FM host locking lips with a new man on the balcony of her Clovelly home on Sunday afternoon
Daily Mail can exclusively reveal the man making Jackie smile again is Richard Ryan – a pilot and DJ who has been described to us as a ‘big name in the eastern suburbs’
A charter pilot, DJ and marketing executive, Richard has been a fixture of Sydney’s social circuit for years now.
Well-connected and charismatic, he’s as comfortable behind the controls of a private jet as he is spinning tracks at a party – or so we are told.
It appears he wasn’t single for long before coming into Jackie’s orbit.
He was previously engaged to a vegan chef named Emma, with the former couple becoming engaged while kayaking around Sydney Harbour in 2021.
Emma – we have chosen not to reveal her last name for privacy reasons – had even been dress shopping for their wedding.
She looks to have selected a $6,500 couture gown, which was later listed for sale online as never worn.
As recently as January, Emma was updating a Pinterest board brimming with wedding inspo content. It’s unclear when exactly they split.
It comes after Jackie was forced to deny rumours in June that she was dating former NRL star Adam Muir, after the pair were spotted on a stroll in the eastern suburbs.
Our photographer spied the pair chatting in the sun for several minutes, with Jackie seen leaning for a kiss at one stage with a huge smile across her dial
A charter pilot, DJ and marketing executive, Richard has been a fixture of Sydney’s social circuit for years now
He kept things casual in a black T-shirt, cap and shades
Mother-of-one Jackie opted for a white tee and jeans
The pair looked smitten as Jackie’s Cavoodle puppy Sadie watched on
She set the record straight live on The Kyle and Jackie O Show, confirming she was still single while laughing off the romance rumours.
Jackie had earlier revealed on the podcast Her Best Life that she was ‘very happy’ and in ‘such a good place’ after previously allowing her marriages to become stale.
‘In all my relationships, I have allowed it to get to a brother and sister dynamic,’ she told her co-host and manager Gemma O’Neill.
This complacency would lead to a lack of intimacy that left Jackie feeling ‘undesirable’ and the partnership ‘unfixable’.
Still, Jackie acknowledged that her experience was not unique, with many of her friends having gone through similar situations in their marriages.
‘The more I spoke to women, the more I realised this is actually really common in a lot of marriages. Like there’s just no sex anymore,’ she said.
She then revealed that her personal life was looking up, without going into details.
Richard was previously engaged to a vegan chef named Emma, with the former couple becoming engaged while kayaking around Sydney Harbour in 2021
Emma had even been dress shopping for their wedding. She looks to have selected a $6,500 couture gown, which was later listed for sale online as never worn (pictured: the listing)
In another episode of the same podcast, Jackie admitted she was struggling to let go of an ex.
Despite being ‘over’ that relationship, she said that in her weaker moments she would think to herself, ‘That’s my person’.
She revealed that the man, whom she did not name, ‘didn’t show up’ for her when she needed him to.
Her last romantic entanglement was with Jack Tyerman – who has since announced his engagement to another woman.
She stated on air that Jack was not her boyfriend, even though she confirmed she was ‘dating’ at the time and they were pictured together on several occasions.
If she does eventually make things official with Richard, he’ll be her first confirmed relationship since her 2018 split from second husband Lee Henderson, with whom she shares a daughter
Her last romantic entanglement was with Jack Tyerman (right) – who has since announced his engagement to another woman
‘Jack is a good friend of mine. I know him through a friend of ours. We didn’t meet on a dating app or anything like that,’ she said in August 2023.
After she told the Daily Mail at the Logies she was dating someone, Jackie later blamed herself for the media running with the story.
If she does eventually make things official with Richard, he’ll be her first confirmed relationship since her 2018 split from second husband Lee Henderson, with whom she shares 15-year-old daughter Kitty.
Before meeting Lee, she was married to the radio presenter ‘Ugly’ Phil O’Neil.
Jackie and Richard were both contacted for comment but did not respond.
READ THE LATEST FROM DAILYMAIL+
Here are some great stories you may have missed:
