Sydney radio ‘queen’ Jackie ‘O’ Henderson has been shock jock Kyle Sandilands‘ ‘work wife’ for 25 years, but the KIIS FM duo have never hooked up.

Taking listener calls for an Ask Me Anything segment on Thursday, Kyle put to rest at least two decades of speculation about his on-air chemistry with single Jackie.

‘Mate, I’m just wondering,’ a listener called Craig began.

‘I don’t know if you ever have or haven’t, but how come you’ve never hooked up with Jackie O?

‘As it seems to be the type of woman you like?’

‘You must be a new listener Craig!’ Kyle responded as Jackie burst out laughing.

Kyle Sandilands has revealed the real reason why he’s never hooked up with Jackie ‘O’ Henderson. The pair are pictured passionately kissing in an advertisement for 2Day FM in 2003

Taking listener calls for an Ask Me Anything segment on Thursday, Kyle put to rest at least two decades of speculation about his on-air chemistry with single Jackie

‘She is lovely. We’re best friends,’ Kyle answered.

‘We’ve been knowing each other, for like… I don’t go out with her girlfriends and get on the p**s and look for blokes, it’s not that sort of friendship.

‘But it’s a solid friendship. We’ve never hooked up.’

Newsreader Brooklyn Ross interrupted: ‘Well, you kissed in a TV ad didn’t you?’

‘Well that’s like being an actor,’ Jackie said.

‘You were still making out,’ Brooklyn interjected, which both radio hosts quickly shut down.

‘We did kiss in that one ad, but it’s never been on the agenda has it? For either of us,’ Kyle insisted.

‘When we met, you weren’t single. I wasn’t single,’ Jackie added.

‘She is lovely. We’re best friends,’ Kyle told a listener. ‘We’ve been knowing each other, for like… I don’t go out with her girlfriends and get on the piss and look for blokes, it’s not that sort of friendship’

Jackie said she and Kyle hadn’t ever been single at the same time, and neither of them had ever had any romantic intentions towards one another

‘I had just met Lee (my ex-husband) and that began an 18 year relationship. Then I got single.’

‘—Then she got fat so come on,’ Kyle joked.

‘When I became single and separated from Lee, what was your status?’ Jackie asked him.

‘Who knows, it’s hard to keep track,’ Kyle said. ‘You probably would’ve been more concerned with your own situation. It’s hard to remember.’

Kyle married his wife Tegan Kynaston – who is also a petite blonde – in at a heritage-listed mansion in Sydney’s Darling Point in front of 130 guests in April 2023.

They have a one-year-old son together, Otto.

In 2018, Kyle was still in a long-term relationship with model Imogen Anthony, who he split from in November 2019 before going public with his former personal assistant, Tegan.

Jackie is currently single after splitting from ex-husband Lee Henderson in 2018, to whom she was married for 15 years

The Kyle and Jackie O Show hosts have been best friends and on-air partners since 2000

The radio star was previously married to her former radio co-host Phil O’Neil for four years, before they divorced in 1999.

Australia was shocked when the radio co-hosts passionately locked lips in an advertisement for 2Day FM in 2003.

Kyle told listeners in 2017 that Jackie’s husband Lee became excited at watching the intimate scene unfold.

While discussing the filming on-air, Kyle claimed that Lee was ‘one of those weird husbands’ because he wanted to watch his wife kiss another man.

‘It was weird though because Jackie’s husband was there on set,’ he said.

‘And I was thinking can’t you cut this guy loose. But he was actually quite good because he was like, one of those husbands that everyone knows, one of those weird husbands there who wanted to watch. And he was giving us critiques.’

In the iconic ad, Jackie O and Kyle are seen looking at each other longingly as the sit behind their microphones.

In a voice-over, Jackie says: ‘You know, people always think there’s something going on between Kyle and I. They think we used to date or maybe had a one night stand.’

‘Nothing has ever happened between the two of us. I couldn’t even imagine him that way,’ she said, before footage plays of the pair walking into a lift together.

After the lift doors close, Jackie throws Kyle against a wall and starts kissing him passionately.

‘Oh Jackie you’re not ramming him up against the lift hard enough. Get right into it!’ Kyle imitated.

‘Yeah but that’s what the ad required- over the top!’ Jackie hit back.

The pair re-created the advertisement in 2015, only Kyle was filmed making out with a Jackie lookalike, while Jackie was paired up with a dog.