Kyle Sandilands has revealed what he really thinks about Jackie ‘O’ Henderson’s new boyfriend.
The 54-year-old radio personality didn’t hesitate to share his thoughts when asked about her rumored boyfriend at an event in Sydney on Wednesday.
Okay, so you will NOT believe this! Pictures surfaced in September of Jackie – MY Jackie – totally making out with this guy, Richard Ryan. Apparently, it happened right at her house in Clovelly! A pilot AND a DJ? Seriously? I’m trying not to freak out, but it’s EVERYWHERE! I just… I needed to share it with someone, anyone! It’s just… Jackie!
But it seems Jackie’s KIIS FM breakfast show co-host is in the dark about her new squeeze.
He jokingly asked his coworker, ‘Who is that in the picture?’ Jackie responded with a bit of embarrassment, saying she’d rather not talk about it and keep it a secret.
‘So he’s not special?’ Kyle egged on his co-host.
Jackie clarified that things with her partner might be getting serious, suggesting their relationship is more than just a casual one.
Kyle pressed Jackie further, explaining that if the person wasn’t significant or unlikely to appear again, they wouldn’t include them in the published version.
‘That’s not what I said…’ she reaffirmed.
‘What are you saying then?’ he pushed, to which she brushed her co-host off.
Last month, Jackie sparked rumors when photos surfaced of her kissing Richard, a well-known figure in the eastern suburbs.
Richard appeared to have a black eye, likely from playing sports, but he didn’t let it bother him as he showed affection for the wealthy radio personality.
He dressed down for the occasion in a simple black T-shirt, cap, and sunglasses. Jackie, a mother of one, chose a more classic look with a white T-shirt and jeans.
Jackie and the other person were talking and laughing in the sunshine for several minutes. At one point, Jackie playfully leaned in as if to kiss them, beaming with happiness.
Richard is a well-known figure in Sydney society, working as a charter pilot, DJ, and marketing executive. He’s been a regular at social events for many years.
He’s equally at home piloting a private jet or DJing a party – a truly versatile and engaging person.
It appears he wasn’t single for long before coming into Jackie’s orbit.
He used to be engaged to Emma, a vegan chef. They got engaged in 2021 while kayaking in Sydney Harbour.
Emma, whose last name we are withholding to protect her privacy, had been looking at wedding dresses.
She appeared to have chosen a $6,500 designer gown, but it was later offered for sale online, still brand new with tags.
Just last January, Emma was still collecting wedding ideas on Pinterest. It’s unknown when she and her partner actually broke up.
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2025-10-30 04:34