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Harry Styles’ 5 biggest surprises: from dating Olivia Wilde to getting Kendall Jenner to rank Kourtney worst Kardashian parent on The Late Late Show

The endlessly surprising Harry Styles. Photo: @harrystyles/Instagram
The endlessly surprising Harry Styles. Photo: @harrystyles/Instagram

  • He starred in Christopher Nolan’s Dunkirk and will soon appear in Don’t Worry, Darling with girlfriend Olivia Wilde, 10 years his senior
  • The former One Direction singer wore a Gucci dress on the cover of Vogue magazine’s December 2020 issue

Dry your eyes, Stylers! The rumours are just that – rumours! A TikTok video alleging that Harry Styles is engaged to Don’t Worry, Darling director and co-star Olivia Wilde went viral last week, but neither party has confirmed (or denied, admittedly …) the allegations. 

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But let’s be honest: a whirlwind engagement wouldn’t be the most shocking thing to surface about the 27-year-old musical artist. Styles has had his fair share of media frenzy since his rise as a member of British pop boy band One Direction – and he’s taken it all in his stride.

Here are five moments in Styles’ fabulously eccentric life that have made the Twitterverse go cuckoo. 

When he publicly started dating Olivia Wilde

Style’s new relationship with the 36-year-old actress and filmmaker was big news for Stylers, as fans of the English singer and songwriter are known, not least because of the couple’s 10-year age gap

Wilde had separated from her long-time fiancé, Jason Sudeikis, before reports surfaced that she was dating Styles. TMZ confirmed their relationship at the beginning of January, after photographs of the couple at a Covid-safe wedding in Montecito, California, were published online.