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  1. May 6, 2024 · How did the stars meet, fall in love and break up after two years of dating? See the photos and details of their romance from September 2020 to May 2024.

    • 57 sec
    • Nicole Briese
  2. Jul 30, 2023 · Olivia Wilde, Sydney Chandler, and Harry Styles attend the Don't Worry Darling red carpet at the 79th Venice International Film Festival on September 05, 2022. Stephane Cardinale - Corbis/Getty Images

    • Whitney Perry
  3. Feb 23, 2023 · December 2021: Harry is getting to know Olivia's kids. As the two inch closer to their one-year anniversary, Wilde has taken their relationship to the next level by introducing Styles to her two ...

  4. Sep 22, 2022 · How did the pop star and the director meet and fall in love? See the key moments of their romance, from filming Don't Worry Darling to attending Coachella, in this detailed timeline.

    • Hannah Dailey
    • harry styles and olivia wilde1
    • harry styles and olivia wilde2
    • harry styles and olivia wilde3
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    • harry styles and olivia wilde5
  5. May 30, 2022 · The singer and the actress are \"more serious than ever\" after meeting on the set of their film Don't Worry Darling, a source tells PEOPLE. They support each other's careers, spend time in London and co-parent Wilde's kids with ex-fiancé Jason Sudeikis.

    • Lindsay Kimble
    • 1 min
  6. Sep 23, 2022 · Harry Styles stars as Jack, a husband who works in a secret facility, and Olivia Wilde directs and co-stars as Alice, a housewife who questions her life. Don't Worry Darling is a 2022 drama mystery thriller film with Florence Pugh, Chris Pine and more.

  7. Aug 19, 2022 · The pair held hands while stepping out of a restaurant. Olivia Wilde and boyfriend Harry Styles couldn't help but show off their love while on a rare date night in New York City. The actors had a ...

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