Madonna’s performance with Britney Spears and Christina Aguilera at the 2003 VMAs was a huge pop culture moment. And when she made out with Spears–and the camera quickly cut, hilariously, to a shocked Justin Timberlake–it was even bigger.

Then the tender age of 44, Madonna’s antics were sensational but not overly strange. Twelve years later, she’s involved in another high-profile makeout sesh, this time with former Canadian Bildungshow star Drake, nearly thirty years her junior.

And it definitely gets weird.

After the borderline Baby Boomer tilts the rapper’s head back and goes in for the kill, something clearly goes wrong. When the moment passes and Drake is released from the lip-tongue death grip, he leans forward, clutching his mouth with an unusual look on his face.

Is it pain? Is it disgust? Is he struggling to breathe? Was the encounter with a fading, attention-craved pop star a haunting reminder of his own mortality and the ephemeral quality of showbiz relevance?

Perhaps we’ll never know. But he was probably just grossed out.