Jackie ‘O’ Henderson has revealed she had a ‘missed connection’ with a handsome man in Sydney’s Eastern Suburbs.
The radio star, 49, described the man, who she crossed paths with on Wednesday evening during a walk as ‘so nice looking’ during Thursday’s Kyle and Jackie O Show.
‘We locked eyes and smiled at one another,’ said Jackie, before describing the moment as being like something out of ‘an Ashton Kutcher movie’.
She revealed the pair shared several long looks, before Jackie finally looked back and ‘smiled and waved at the man.’
But the mother-of-one said she later described what she was wearing to her mother – and revealed her mum Julie’s brutal reaction to the outfit.
Jackie ‘O’ Henderson (pictured) has revealed she had a ‘missed connection’ with a handsome man in Sydney’s Eastern Suburbs
Henderson said she had been wearing Birkenstock sandals, a T-shirt, a bucket hat and no makeup during the encounter.
‘It’s a wonder he even looked at you,’ Jackie recalled her mother saying.
The radio station later put out a call over social media asking for the public’s help to locate the mystery man.
Jackie has been single since divorcing her ex-husband Lee Henderson in 2018.
Last month, the radio star opened up about the struggles she’s faced with loneliness on the dating scene.
Speaking with fans at Luke McLeod’s book launch for Everyday Enlightenment, the radio titan admitted she is ‘desperate’ to find love and companionship once more.
She explained she had lunch with McLeod last year when they got onto the topic of her love life and how she felt she was ‘missing something’.
Jackie ‘O’ Henderson (pictured) shocked co-host Kyle Sandilands on Tuesday by revealing she once slept with a man on the first date – and was still getting approached by his friends years later
Jackie went on to tell her fans that Luke gave her a piece of advice in that moment which ‘changed my life’.
He said she was giving off too much ‘desperate energy’, and if she really wanted to attract love in her life, then she needed to be grateful for what she already has.
Jackie has been married twice in the past, with her first husband being DJ ‘Ugly’ Phil O’Neil in the late ’90s.
She was wed to ex Lee from 2003 to 2018 and the couple co-parent their daughter, Kitty.
The blonde bombshell added despite the encounter happening over 20 years ago she was still bumping into his mates who wanted to know the dirty details