Olivia Wilde isn’t the only major star Harry Styles has been romantically involved with.

Here is a look at the “Watermelon Sugar” singer’s dating history, from Taylor Swift to Kendall Jenner.

2011: Caroline Flack

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.

“I already knew that he had a crush on me, he’d made it pretty obvious,” she had written in her autobiography, “ Storm in a C Cup .” ( via Seventeen .) “He’d said it in magazines and he’d said it to friends.”

The pair eventually broke up after being criticized for their age gap.

Flack died in February 2020 at age 40 by hanging

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