Joshua Goldman
Joshua Goldman
min read · September 11, 2025 · Entertainment

Olivia Wilde's 'Surprised' Reaction to Harry Styles Dating Zoe Kravitz

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

The Love Lives of Hollywood's Elite: A Web of Romance and Intrigue

The world of celebrity romance is always a wild ride, and this week is no exception. Olivia Wilde, 41, is reportedly "surprised" that her ex-boyfriend Harry Styles, 31, has started dating her friend Zoe Kravitz, 36. The news has sparked a flurry of gossip, with sources close to the actress claiming that she's finding it all rather awkward.

For those who may have forgotten, Wilde and Styles had a high-profile romance from early 2021 until November 2022. During their time together, they were said to be deeply in love, with some even speculating that Wilde was the inspiration behind Styles' hit song "As It Was." But it seems that now, at least, the singer is moving on – and fast.

Kravitz at the Caught Stealing New York Premiere held at Regal Union Square on August 26

According to insiders, Kravitz has been seen on several dinner dates with Styles, and things appear to be getting serious. The news has left some of Wilde's friends feeling uncomfortable, particularly those who are close to her inner circle. "It's like, why her? Why does he have to date people she knows?" one source explained.

But not everyone is as concerned about the situation as you might expect. Another source close to Wilde revealed that she's actually pretty relaxed about Styles' new romance – and has even expressed some curiosity about it. "Olivia thought that pairing was interesting, but she doesn't really give a crap because she and Harry dated so long ago," they said.

Of course, this isn't the first time we've seen Styles get tangled up in a romantic web with his exes. In fact, he's made a bit of a habit of dating women who are part of his professional or social circle – including his Don't Worry Darling co-star Florence Pugh and singer Taylor Swift.

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

But what about Kravitz? The 36-year-old actress has been linked to several high-profile romances in the past, including with Ben Foster, Ezra Miller, Penn Badgley, and Chris Pine. And let's not forget her brief marriage to Karl Glusman – or her highly publicized engagement to Channing Tatum.

Despite all this drama, it seems that Styles is smitten with Kravitz. Insiders claim that the two have been inseparable since they started dating, and that things are getting more serious by the day.

Meanwhile, another celebrity romance has caught our eye – this time between Austin Butler and Emily Ratajkowski. The two were spotted together on a cozy dinner date in New York City, with sources claiming that things are heating up between them.

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

Butler, who was most recently linked to Kaia Gerber, has been seen getting close to Ratajkowski on several occasions – including at the afterparty for their movie Caught Stealing. And it seems that he's smitten with her creative energy: "You learn a lot … The ideas that she comes up with are really creative and nuanced, and she understands story," he gushed.

Ratajkowski, 34, has been linked to several high-profile romances in the past – including Styles himself. And it seems that Butler is now vying for her attention. But what about Zoe Kravitz? Is she still on Styles' radar?

Only time will tell, but one thing's for sure: the world of celebrity romance is always full of surprises.

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

[TheScholarlyNote.com reached out to Olivia Wilde's rep for comment but did not hear back at the time of publication.]

Update: Austin Butler and Emily Ratajkowski have been spotted together several times in recent weeks, including on a dinner date in New York City. The two were seen laughing and smiling together, with Butler even flinging an arm around her shoulders.

[This article was originally published on [TheScholarlyNote.com].]

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'