Olivia Wilde

In January 2021, Harry and Styles and 'House' actress Olivia Wilde were revealed to be dating after a photo of them holding hands was published.

They quickly became one of the most famous couples on the planet and Harry, 29, one again proved his penchant for older women by hooking up with Olivia, 39.

Harry went on to star in psychological thriller 'Don't Worry Darling', which was directed by Olivia.

The promotional tour for the film in September 2022 was full of drama, with reports of a feud between Harry's co-star Florence Pugh and Olivia, as as between him and actor Chris Pine.

Harry and Olivia called it quits in November 2022 due to his touring commitments, whilst she had to stay in LA for her two children Otis, eight, and five-year-old Daisy, whom she raises with her former husband Jason Sudeikis.