The One Woman Both Prince Harry And Harry Styles Were Once Linked To

When Harry Styles began dating Olivia Wilde, the media was quick to point out their 10-year age gap, but it wasn't the first time Styles had dated a much older woman. According to Glamour UK, the pop star met TV presenter Caroline Flack on "The X Factor" in 2011 when he was 17 and she was 31. "I already knew that he had a crush on me, he'd made it pretty obvious," Flack wrote in her autobiography, "Storm in a C Cup" (via Seventeen). "He'd said it in magazines and he'd said it to friends." The two then struck up a relationship, which wasn't well received by One Direction fans. Writing that things began to go south when Styles was spotted leaving her house one morning, Flack added, "It was open season ... In the street, people started shouting at me 'pedophile' and 'pervert.'" It was this negative attention that ultimately prompted the couple to break things off.

But, before Styles, Flack was also dogged by the paps for her tryst with Prince Harry, as the Duke of Sussex detailed in his memoir, "Spare" (via Hello!). As soon as photos of the two hit the Internet, "Within hours a mob was camped outside Flack's parents' house, and all her friends' houses, and her grandparents' house," Harry explained. In the end, as much as they might have liked each other, the media attention became too much to handle.

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