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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. Feb 23, 2023 · When photographs of Harry Styles and Olivia Wilde holding hands hit the Internet, it seemed as though the world was desperate to find out everything they could about the fledgling couple.

  3. 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
    • olivia wilde and harry styles1
    • olivia wilde and harry styles2
    • olivia wilde and harry styles3
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  4. Jul 30, 2023 · From "Don't Worry Darling" to that infamous salad dressing fight, here's a complete timeline of Harry Styles and Olivia Wilde's relationship and breakup.

    • Whitney Perry
  5. Mar 20, 2024 · Here's a complete timeline of Harry Styles and Olivia Wilde's relationship, including how they met and how her ex Jason Sudeikis is handling the news to why they ended things in November...

    • 2 min
  6. Apr 24, 2021 · How did the actors go from co-stars to lovers amid Jason Sudeikis's heartbreak? See the key moments of their romance, from flirty Instagram comments to pub dates in London.

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  8. Aug 19, 2022 · 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 romantic day yesterday, starting off with a gym...

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