Olivia Wilde’s feelings about her friend Zoë Kravitz dating her ex, Harry Styles

Zoë Kravitz, 36, and Harry Styles, 31, are Hollywood’s hottest new couple. As fans watch and wait to see how their future unfolds, people can’t help but think about their past. For Styles, one of his last big relationships was Olivia Wilde, 41, who happens to be friends with Kravitz.

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Harry Styles and Olivia Wilde began dating after filming ‘Don’t Worry Darling’

Wilde and Styles went public in January 2021, and it was a whirlwind relationship that involved breakups, special salad dressing, and an eventual split in November 2022. Now that Styles is dating Kravitz, a source told DailyMail she is “surprised” to see them dating.

Styles and Kravitz have been going viral since they confirmed their relationship in late August. A friend reportedly said, “It feels weird” for Wilde when he starts “dating a new celebrity,” especially someone in her circle. “It’s like, why her? Why does he have to date people she knows? It’s super awkward for her,” they told the outlet.

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Styles and Kravitz have been photographed in different countries over the past months

Moving on

However, another source told the outlet the Year One star “doesn’t give a crap” about it, noting they broke up three years ago. Plus, Wilde has already moved on. The actress was recently spotted kissing Caspar Jopling, Ellie Goulding’s ex.

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Olivia Wilde and Caspar Jopling

Wilde and Jopling were spotted smooching after a romantic dinner in London this week. They are both parents, with Jopling sharing a 4-year-old son named Arthur with Goulding, and Wilde sharing son Otis, 11, and daughter Daisy, 8, with her ex, Jason Sudeikis.

The Don’t Worry Darling actress has kept her relationships private, including Styles. When they were still together in 2022, she told Variety, “I’m not going to say anything about it because I’ve never seen a relationship benefit from being dragged into the public arena.” So it’s safe to say we probably won’t hear anything from Wilde herself about her love life.

The new fling comes after she was spotted looking coupled up with a former basketball player named Dane DiLiegro in January 2025. At the time, an insider told DailyMail she was able to “finally” move on from her breakup with Styles.

© Allen Berezovsky
Olivia was dating Dane Diliegro earlier this year

When she and Styles split, a source told PEOPLE it was a “very amicable decision,” but noted “The break has been difficult for Olivia.”

The source explained that she learned a big lesson from their relationship, saying she “got way too caught up” and it “became a public spectacle,” adding she is determined not to repeat that “mistake ever again.”