Caroline Flack

Harry met Caroline Flack when she was a presenter on ‘The Xtra Factor' - 'The X Factor' spin-off show - and the two were romantically linked in 2011 after he was spotted leaving her house. He was 17 at the time and she was 31.

“I already knew that he had a crush on me, he’d made it pretty obvious. He’d said it in magazines, and he’d said it to friends,” the presenter wrote in her autobiography ‘Storm in a C Cup.’

Days after Flack's tragic death in 2020 at the age of just 40, Styles attended the BRIT Awards wearing a black remembrance ribbon.