At the time, the singer sparked major romance rumors with the actress after they were spotted holding hands at a friend’s wedding. The New York Post’s Page Six published photos of Harry and Olivia dressed to the nines and wearing masks while attending the “Golden” singer’s manager’s wedding in Montecito, California. The series of pics immediately sparked romance rumors as the Booksmart director and British crooner looked like more than just friends with their hands interlocked.
As fans know, Harry is starring as Jack in the upcoming thriller Don’t Worry Darling, which Olivia is directing. In September 2020, news broke that the X Factor alum would replace Shia LaBeouf in the period piece and star alongside Florence Pugh and Chris Pine. After filming on the movie wrapped in February 2021, Olivia praised her man with an Instagram post.
“Little known fact: most male actors don’t want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it’s so hard to get financing for movies focusing on female stories. No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight,” she wrote. “Enter: @harrystyles, our ‘Jack.’ Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our ‘Alice,’ but he infused every scene with a nuanced sense of humanity. He didn’t have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth and ability to drive backwards.”
Prior to the pair’s seemingly romantic outing, Olivia was engaged to comedian Jason Sudeikis since 2012. The former couple — who share a son named Otis and daughter named Daisy — split in October 2020 after nearly 10 years together. Harry, for his part, was previously linked to Taylor Swift, Kendall Jenner, Cara Delevingne, Nadine Leopold, Georgia Fowler, Tess Ward, Camille Rowe and more famous faces.
In December 2020, a source told Us Weekly that Harry was staying away from the dating scene amid the coronavirus pandemic. “His dating life has been pretty nonexistent during lockdown because he’s been so careful to respect quarantining rules and social distancing,” the insider said. “He’s got some options in the pipeline in terms of who he’d like to date under the right circumstances, but nothing intense or formal.”
So, what changed his mind about stepping out with a possible significant other? Scroll through our gallery for all the details on Harry and Olivia’s relationship.
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