The 43-year-old interviewed the pop princess on 60 Minutes about her latest album Golden, and asked her how she was feeling about turning 50.
'My friends say 'Do you know what? I'm just going to try to enjoy myself, I'm just going to try love the people I love, do the best I can, understand as best as possible where I am in the world, where I may have stuffed it up, where I am at the moment,' she said.
Karl responded: 'Well, you're doing it very well. I mean, it helps obviously that you're a hot 50-year-old.'
The pair later touched on the subject of ageing, with Kylie revealing although she's become more resilient as a person, she still has a 'fragile' side.
'There's definitely that fragile side and I don't think that's a bad thing either,' she said to Karl.
'The softer side, the vulnerable side, the side that's able to be hurt,' he responded, to which Kylie replied: 'Yes, otherwise what's the point? I'm just going for things.'
He then brazenly advised: 'On the subject of going for things, can you stop going for incredibly good-looking d**kheads?'
Viewers of the program took to Twitter to slam Karl's bizarre interviewing technique, labelling him 'creepy' and 'misogynistic'.
This comes as another blow to Karl, who made headlines last week after his taxi driver leaked an explosive phonecall the Today Show host made during the ride.
In the shocking rant, Karl slammed his colleagues, other network shows and even his bosses in the attack. He claimed that his co-host Georgie Garnder needs to ‘step up’ and called Nine bosses ‘out of touch’.