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Olivia Wilde is ‘surprised’ her ex-boyfriend, British pop singer Harry Styles, is dating her good friend Zoe Kravitz.
Wilde, 41, famously dated the One Direction singer, 31, from early 2021 to November 2022 after they bonded on the set of her movie Don’t Worry Darling.
Their romance came after Wilde split with her partner of seven years, Jason Sudeikis, with whom she shares two children: Otis and Daisy.
Despite Styles’ reputation with his long list of exes, things appeared serious with Wilde and she’s even rumored to be the inspiration behind his hit song As It Was.
Although Wilde herself has moved on too, most recently with Ellie Goulding’s ex Caspar Jopling, sources say Styles’ romance with her friend Kravitz, 36, is awkward for her.
‘Olivia is surprised Harry is dating Zoe,’ a source told Daily Mail. ‘It always feels weird to her when Harry starts dating a new celebrity.’
Another source said she really ‘doesn’t give a crap’ because they broke up so long ago.

Olivia Wilde is ‘surprised’ her ex-boyfriend, British pop singer Harry Styles, is dating her good friend Zoe Kravitz. Seen in June in Greece


Zoe, left, and Harry, right. They were seen on a date last week in New York City. The two walked close together as they headed to dinner
Zoe – who is five years younger than Wilde – is just too close to Olivia’s circle of friends, which makes it uncomfortable, the source explained.
‘It’s like, why her? Why does he have to date people she knows? It’s super awkward for her,’ added the friend.
Another pal of Wilde’s who romanced Styles is 34-year-old supermodel Emily Ratajkowski. Styles and Ratajkowski were seen making out in Tokyo in March 2023. The pair were French-kissing on a street which was the beginning of their very brief romance.
A second source had a very different outlook: ‘Olivia thought that pairing was interesting, but she doesn’t really give a crap because she and Harry dated so long ago. I mean, they broke up three years ago.’
Daily Mail has reached out for comment to Wilde’s rep but did not hear back at the time of publication.
Other women Styles has dated are his other Don’t Worry Darling costar Florence Pugh as well as Taylor Swift and Kendall Jenner.
Before Kravitz was seen on a dinner date with Styles, she got close to another budding A-list actor.
The Big Little Lies actress was flirty with Austin Butler, her Caught Stealing costar.

Wilde and Kravitz seen at a YSL event in Los Angeles in March 2023

Wilde, 41, dated the One Direction singer, 31, from early 2021 to November 2022 after they bonded on the 2020 set of her movie Don’t Worry Darling; March seen in 2022
When on their press tour they looked each other in the eyes, touched each other’s arms and hung out together after their red carpet duties.
Fans were guessing she was his next celebrity lover after his romances with Vanessa Hudgens and Kaia Gerber.
Austin also raved about Kravitz.
The Elvis star explained: ‘You learn a lot … The ideas that she comes up with are really creative and nuanced, and she understands story. It’s a great thing to get to work with somebody like that.’
Kravitz has dated several stars already including Ben Foster, Ezra Miller, Penn Badgley, and Chris Pine.
She was married to actor Karl Glusman from 2019 to 2021 and was engaged to actor Channing Tatum from 2023 to 2024. And Kravitz has been linked to musician Noah Centineo.

Further complicating matters is Zoe’s love life. There was a question about if she was really dating Styles because she had been so flirty with Austin Butler, her Caught Stealing costar. Seen on August 26 in NYC

Austin also raved about Kravitz. The Hollywood star explained: ‘You learn a lot … The ideas that she comes up with are really creative and nuanced, and she understands story. It’s a great thing to get to work with somebody like that’


Butler (left) was glimpsed indulging in a cozy Friday night tête-à-tête with Ratajkowski (right) in New York City; interestingly, Ratajkowski had romanced Styles in the past
Meanwhile, Butler was glimpsed indulging in a cozy Friday night tête-à-tête with Ratajkowski in New York City.
Austin and Emily were seen grabbing cocktails together while nestled in a booth at the West Village nightspot, the Waverly Inn.
Under the dim lighting and the beloved murals by Edward Sorel, Emily and Austin seemed enraptured with each other’s company, with him flinging an arm along the back of the booth behind her, in an image obtained by TMZ.
Austin and Emily also crossed paths the week before at the afterparty for the Caught Stealing premiere, as seen in a snap of the event posted by writer Matt Weinberger.
One of the photos in his Instagram album about the party showed Austin turning back towards Emily, who herself was gazing at something unseen off-camera.