Olivia Wilde was reportedly "surprised" to learn that her ex, singer Harry Styles, has been seen dating her friend Zoe Kravitz, multiple insiders told the Daily Mail.
Wilde, 41, and Styles, 31, dated from early 2021 until November 2022 after meeting on the set of Wilde's film Don't Worry Darling. The relationship followed Wilde's split from Jason Sudeikis, with whom she shares two children, Otis and Daisy. Sources quoted by the Daily Mail said Wilde found the Styles–Kravitz reports awkward because Kravitz is part of her wider social circle, while other close friends told the outlet Wilde is largely unbothered because the breakup occurred several years ago.
The Daily Mail reports that Styles and Kravitz, 36, were seen on a dinner date in New York City after being photographed together in June in Greece. One source told the outlet: "Olivia is surprised Harry is dating Zoe. It always feels weird to her when Harry starts dating a new celebrity." Another friend of Wilde's told the paper she "doesn't give a crap" because the relationship ended three years ago.
Wilde and Kravitz have been linked publicly in the past; they were photographed together at events while both remained active in film and fashion circles. The Daily Mail also noted Wilde and Kravitz attended a YSL event in Los Angeles in March 2023.
A second source to the Daily Mail framed the matter differently, saying Wilde found the pairing "interesting" but not personally troubling. The outlet said it reached out to Wilde's representative for comment and did not receive a response.
Styles' high-profile dating history has attracted sustained public attention. Since rising to fame with One Direction, he has been linked to a string of celebrities, including Taylor Swift, Kendall Jenner and Florence Pugh, and has been the subject of media coverage for on-again, off-again public romances. Styles and Wilde's relationship began during the 2020 production of Don't Worry Darling; their time together and interactions on the film's press tour were widely reported. Some outlets have speculated the relationship influenced certain songs on Styles' recent albums, though such claims are typically framed as unconfirmed.
Kravitz, an actress and singer known for roles in films and television, has a public history of relationships with several actors and high-profile figures and was previously married to actor Karl Glusman from 2019 to 2021. Kravitz has also been linked to other actors through recent projects and premieres, where photographers and industry guests sometimes spot informal interactions among co-stars.
The Daily Mail story referenced another friend of Wilde's who previously dated Styles, model Emily Ratajkowski, noting the interwoven nature of social and professional circles in Hollywood. The report said that such connections contribute to the awkwardness Wilde purportedly felt when the pairing was reported.
Representatives for Styles and Kravitz did not immediately comment to the Daily Mail in the story published Monday. The actors and musicians involved have not publicly addressed the reports through their own social channels as of publication.
The reported development underscores how relationships among public figures can draw renewed attention when new pairings involve overlapping circles. For Wilde, Styles and Kravitz, the intersecting professional histories — including Don't Worry Darling for Wilde and Styles, and Kravitz's ongoing acting work — provide the broader context that media outlets have highlighted while reporting on reactions from within their social network.
Daily Mail was the primary source for the accounts of Wilde's reaction cited in this article. Requests for comment from representatives named in that report were not confirmed by the outlet at the time it published its story.
Further developments, including any public statements from Wilde, Styles or Kravitz or additional reporting from the parties' representatives, may provide clearer context about the nature of the relationships and the reactions described by the Daily Mail sources.