Harry Styles has been linked with many dating partners over the decade, including the American actress and director, Olivia Wilde. The two stars first met in September 2020 and dated each other for over two years between 2020 and 2022.
Styles and Olivia had come together for the shooting of the mystery thriller film, Don’t Worry Darling. It was the second movie to be directed by Olivia Wilde and featured Florence Pugh and Styles in the lead and supporting roles, respectively.
A January 2021 report from People confirmed that Harry Styles and Olivia developed a friendship in late 2020 as they spent time shooting the movie. The report also hinted that their friendship developed into a romantic relationship soon after and that they were very serious about it.
The news of the pair’s romance came on the head of Olivia Wilde’s split with Jason Sudeikis in early 2020. Jason had been Olivia’s fiancé for seven years, and the couple shared two children. They are blessed with a daughter, Daisy Josephine, who was four then, and a son, Otis Alexander, who was six.
A look at the timeline of Harry Styles and Olivia Wilde’s relationship
Harry Styles and Olivia Wilde shared one of the most high-profile relationships in the music and film industry that lasted over two years. The couple mostly kept their dating life private but were often spotted cherishing their time together.
Here’s the full timeline of the relationship between Olivia Wilde and Styles:
(1) Harry Styles holds Olivia’s hands while attending a wedding – January 2021
Page Six reportedly confirmed the dating speculations in January 2021 after publishing pictures of the pair holding each other’s hands at a wedding. The two stars were photographed when they were attending the wedding of Styles’ agent at the San Ysidro Ranch in Montecito, California.
(2) Styles and Olivia photographed in Italy engaging in some PDA – July 2021
Page Six published another round of images of the couple in July 2021 as they engaged in some public display of affection (PDA). The pair were photographed hugging, kissing, and basking in the sun together while donning matching swimwear.
(3) Olivia attends the opening night of Harry Styles’ Love on Tour – September 2021
An E! News report from September 2021 confirmed that Olivia Wilde attended the first night of Styles’s Love on Tour outing in Las Vegas. She reportedly sang along to most of the songs.
(4) Olivia was spotted wearing a cross necklace like Styles – November 2021
Olivia attended the Gucci Love Parade donning a golden cross necklace, which seemed very identical to the one Styles wears. The similarities were further confirmed when she posted a picture of her on Instagram from the fashion show.
(5) Harry Styles meets Olivia Wilde’s children – December 2021
A People report from December 2021 confirmed that Styles spent some time with Olivia’s two children, and was slowly getting to know them. Olivia was also reported to have met Styles’ mother.
(6) Olivia and Harry Styles spotted in Italy – May 2022
A People report from May 2022 confirmed the pair donning casual outfits as they walked through the streets in Italy. They were photographed almost two weeks after Wilde was served custody papers by her ex-fiancé, Jason Sudeikis.
(7) Olivia confirmed plans to keep her relationship private – August 2022
While appearing for an interview with Variety in August 2022, Olivia said that she was “not going to say anything about” the relationship. She confirmed her plans to keep it private and added:
“I’ve never seen a relationship benefit from being dragged into the public arena.”
(8) Olivia Wilde busts cheating rumors – September 2022
Olivia interviewed with Vanity Fair for the cover story in September 2022 and busted rumors about her split with her ex-fiance and relationship with Harry Styles. Wilde told Vanity Fair that “our relationship was over long before I met Harry.”
She spoke about her reasons for keeping the relationship private while adding:
“I think once you crack open the window, you can’t then be mad when mosquitoes come in. It’s like, ‘You opened the window.’ “
(9) Olivia Wilde attends Harry Styles’ concert with her children – November 2022
A People report from November 2022 confirmed that Olivia attended Styles’ Kia Forum, California, concert with her children, Daisy and Otis. Olivia was photographed seated in the front row seats with her children at the November 15 concert.
(10) Styles and Olivia Wilde take a break and later split – November 2022
As per a November 2022 report from People, the couple was taking a break after over two years of relationship. It was reported that the couple had different priorities for the time being.
While Styles was engaged in international tours, Olivia was trying to take care of her work in LA and look after her children. Neither of the two confirmed splitting up publically, however, they remained only friends after that.
As of this writing, Harry Styles is not confirmed to be dating anyone. The As It Was singer was recently in the news after he reportedly split up with Taylor Russell in May 2024. Olivia Wilde, on the other hand, is not confirmed to have dated anyone after her relationship with Styles.
