2011: Caroline Flack Hed said it in magazines and hed said it to friends.” The two started dating when Harry was just 17, while Caroline was 31 at the time.

Who did Harry date when he was 16?

Styles was romantically linked to the late Caroline Flack back in 2011 when he was just 17 years old and she was already in her 30s. Styles met the “X Factor” presenter when he competed on the show along with the other members of One Direction.