Jackie ‘O’ Henderson gets asked out on a date after revealing her fears of being single forever – but there is one big problem

After admitting she ‘wasn’t okay’ with spending her life single, it seems Jackie O Henderson is now being bombarded by a bevvy of blokes wanting to date her. 

The radio queen, 49, was put on the spot on Friday when she was asked out live on-air by a Sydney tradie.

But there was one catch – the young Casanova was a teenager.

Kieran, 18, phoned in to The Kyle and Jackie O Show to ask Jackie what her plans were for the weekend.

After telling Kieran she was planning to attend a roller derby event, he wasted no time asking the blonde bombshell if he could tag along. 

He even offered to buy Jackie a Red Bull energy drink. 

After Kieran’s proposal, Jackie wanted to make sure of her potential paramour’s age asking: ‘It says you’re 18 on the screen. Is that right?

‘We don’t have to worry about that,’ came Kieran’s smooth reply. 

Given that Kieran was almost half Jackie’s age, she very much did worry about that.

Jackie ‘O’ Henderson was put on the spot on Friday when she was asked out live on-air by a Sydney tradie 

‘I think we do,’ she replied. ‘My image would be shot if I was dating an 18-year-old. In my head I’d be thinking “this is so inappropriate.”‘

Displaying a Herculean persistence, Kieran responded with: ‘I’m a very mature 18-year-old.’

There must’ve been something in Kieran’s responses that piqued Jackie’s interest, asking the young man to tell her more about himself.

‘I recently just bought a four-wheel drive. I’m a carpenter, nearly fully qualified. Not many 18-year-old’s fully qualified, Jackie,’ he said, selling himself further.

Kieran, 18, phoned in to The Kyle and Jackie O Show to ask Jackie what her plans were for the weekend

Kieran, 18, phoned in to The Kyle and Jackie O Show to ask Jackie what her plans were for the weekend 

The pair bonded even further when the young carpenter left school in year 8 to pursue his trade.

‘I get that,’ Jackie replied. ‘I left in year 10. I didn’t prosper at school at all.’

She then congratulated Kieran on his work ethic saying, ‘good on you, now you’ve got a four-wheel drive.’

Seeing another opportunity to smooth talk the radio star, Kieran jumped in with: ‘Exactly, and it’s got a passenger seat. It looks like it’s got Jackie’s name on it as well.’

It appears that Kieran’s charms may have worked on Jackie who shot back a cooing: ‘Aww, I love you, you’re so sweet.’

After telling Kieran she was planning to attend a roller derby event, he wasted no time asking the blonde bombshell if he could tag along

After telling Kieran she was planning to attend a roller derby event, he wasted no time asking the blonde bombshell if he could tag along 

Jackie said she did want to find love again after newsreader Brooklyn Ross asked the host how she felt about the prospect of spending the rest of her life alone, on Thursday.

‘I am not totally ok with that,’ Jackie said.

‘I don’t think there’s anything wrong with me for wanting that. It is natural for us to want human connection – that’s who we are.

‘The idea of that being forever, that’s not ideal but if you said its going to be for the next three four years I’d be like ok.’

Jackie has been married twice in the past with her first husband being DJ ‘Ugly’ Phil O’Neil in the late ’90s.

Jackie went on to marry UK photographer Lee in 2003 with the pair welcoming their daughter Catalina “Kitty” Henderson in December 2010. 

The couple announced their separation in October 2018, but continue to have an amicable relationship as they co-parent their thirteen year old daughter Kitty.

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