Karl Stefanovic exposed his teenage daughter Willow's crush on the handsome son of United States Ambassador Caroline Kennedy during an interview with the diplomat on Wednesday's Today show.
The breakfast show host, 48, embarrassed his 18-year-old teen on live television when he asked Ms Kennedy, 65, if her son Jack Schlossberg was single.
He went on to say Willow 'wanted him to ask' if the 30-year-old grandson of John F. Kennedy was available for her to date.
Karl asked Ms Kennedy: 'I hope that you don't take any offence to what I am going to ask. My daughter wanted to know if your son is single?'
While his high-profile gest took the question in good spirit, she quickly 'deflected' it by replying: 'You would have to ask him. I can't answer that.'
Karl Stefanovic exposed his teenage daughter Willow's crush on the handsome son of United States Ambassador Caroline Kennedy during an interview with the diplomat on Wednesday's Today show
However when Karl conceded and attempted to move on, Ms Kennedy decided to take control and turn things back on Karl.
'Your daughter must be so mad at you right now. I would be so mad if I was your daughter,' she said.
Flustered Karl tried to joke that he was asking for his three-year-old daughter Harper, and not Willow.
'She is only three! The other one is taken,' he said.
'Then there is something really wrong with you,' Ms Kennedy hit back light heartedly.
The breakfast show host, 48, embarrassed his 18-year-old teen on live television when he asked Ms Kennedy, 65, if her son Jack Schlossberg (right) was single
He went on to say Willow 'wanted him to ask' if the 30-year-old grandson of John F. Kennedy was available for her to date. (Pictured centre: Today co-host Sarah Abo)
Jack (pictured in 2019) has already expressed interest in a political career, and is working closely with his mother in the Pacific region during her tenure as U.S. ambassador to Australia
The awkward encounter comes just a few months after Willow, whose real name is Ava but she prefers to go by her middle name, turned 18.
To celebrate the milestone, Karl had some kind words for his lookalike girl, saying he'll 'love her forever and beyond' alongside a sweet selfie of the pair cuddling up.
He also posted pictures of Willow throughout the years and a fun photo of the teen and her stepmother Jasmine posing up for a mirror selfie in matching pink outfits.
'Happy birthday to our 18 year old goddess. I'm so proud of you. I will love you forever. And beyond,' Karl captioned his post which got more than 7,000 likes.
The awkward encounter comes just a few months after Willow, whose real name is Ava but she prefers to go by her middle name, turned 18
