Harry Styles and Olivia Wilde's Relationship - Who is Olivia Wilde With Now?

Origins: When Film Sparks Romance

Olivia Wilde (born 1984) cast Harry Styles in Don’t Worry Darling in September 2020. Their ages—she was 36, he was 26—sparked occasional headlines about olivia wilde harry styles age. Within months, their friendship on set blossomed into a full-blown romance, with insiders confirming their connection by January 2021 .

They were first seen publicly at a wedding where Styles was the groom’s friend, and he even referred to her as his "girlfriend" during his speech . From yachts in Italy to red-carpet events, they navigated a very public romance for nearly two years .

What Happened with Harry Styles and Olivia Wilde?

Their breakup came in November 2022, ending a nearly two-year relationship. Officially, it was amicable: Harry’s ongoing tour and Olivia’s focus on her kids and directing career created distance and conflicting priorities. There were no public engagement rumors—so no olivia wilde and harry styles engaged ever happened.

Did Olivia Leave Her Husband for Harry?

No. Wilde had already separated from fiancé Jason Sudeikis at the start of 2020, months before meeting Styles. She emphatically denied jumping ship: “The complete [expletive] idea that I left Jason for Harry is completely inaccurate”.

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How Long Did They Date?

From January 2021 to November 2022—almost two years. They worked together for about 1–2 months before their romance was public, then shared close moments until their parting.

Olivia’s Past and Film Set Scandals

Before Harry, Olivia was engaged to Jason Sudeikis from 2013 to 2020. They share two children, Otis and Daisy. The end of their long relationship involved custody and separation, even resulting in legal papers being served publicly at CinemaCon—a major emotional moment for Wilde.

On the Don’t Worry Darling set, rumors of tension between Olivia and co-star Florence Pugh sparked headlines, known as the florence pugh olivia wilde fight scandal . Additionally, Chris Pine—another co-star—was dragged into rumors around Styles, Wilde, and tension on set .

Olivia Wilde Scandal

The most public scandal involved the Don’t Worry Darling behind-the-scenes drama: casting shake-ups, script leaks, and rumors of on-set conflict, especially involving Florence Pugh . While it momentarily overshadowed the film's release, Olivia maintained that normal creative differences sparked the media frenzy.

Who Is Olivia Wilde Dating Now?

As of early 2025, Olivia Wilde is romantically involved with Dane DiLiegro, a 6'8" former professional basketball player turned actor, best known for his role in Prey. They've been spotted together at NBA games, and like Harry, he brings a fresh presence into her life—though on a more private, low-key stage .

⚡ FAQs 

• What happened with Harry Styles and Olivia Wilde?

They started dating after filming Don’t Worry Darling in early 2021 and split in November 2022 due to conflicting careers and priorities .

• Did Olivia leave her husband for Harry?

No—her split from Jason Sudeikis preceded her meeting Styles. She confirmed the relationship with Harry began after the end of her engagement .

• How long did Harry Styles date Olivia Wilde?

About two years—from January 2021 to November 2022 .

• Who is Olivia Wilde in a relationship with now?

As of early 2025, she’s dating Dane DiLiegro, a 36-year-old actor and former basketball pro .

Final Thoughts

Olivia Wilde’s relationship with Harry Styles captured global media attention—fueled by their age difference, film collaboration, and tabloid-driven scandals. But the narrative is deeper: an amicable romance that ended gracefully, followed by Olivia’s mindful pivot to privacy with a new partner. Her journey—from Jason Sudeikis to Harry Styles to Dane DiLiegro—speaks of growth, resilience, and a woman defining her own path.