Harry Styles has had a number of relationships since he stepped into the international spotlight in 2010 and we’re taking a look back at them right here. From the late television presenter Caroline Flack to actress and director, Olivia Wilde, he’s dated women of all ages over the years and the situations have always made headlines.

Harry admitted to having a crush on Caroline when she was a presenter on ‘The X Factor’ during his time on the show. Dating rumors started shortly after in 2011 and the only thing Harry would say about the romance in interviews, was that they ‘got on really well’. Caroline later wrote about their connection in her book, Storm in a C Cup, which was released in 2015.

‘It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season,’ she wrote about the ups and downs of their time together. ‘After that anyone could say anything. In the street people started shouting at me ‘pedophile’ and ‘pervert.’’

Caroline sadly died by suicide in Feb. 2020 and Harry was spotted honoring her by wearing a black ribbon at the 2020 BRIT Awards.