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Olivia Wilde and Harry Styles Kept Their Relationship ‘Under Wraps’ Before PDA Photos Surfaced: ‘They Were Very Careful’ (Exclusive)

Top secret! Olivia Wilde and Harry Styles avoided jumping right into a PDA-packed relationship after she ended her seven-year engagement to Jason Sudeikis.

Related: Olivia Wilde, Jason Sudeikis: Relationship Timeline

A source exclusively tells Us Weekly that the couple kept their romance hush-hush early on. Wilde, 36, and Styles, 26, went to great lengths to avoid letting it slip while working together on the set of their upcoming film, Don’t Worry Darling.

Olivia Wilde and Harry Styles 'Were Very Careful' About Keeping Their Romance Quiet Before Going Public
Olivia Wilde and Harry Styles. Rob Latour/Shutterstock; Nigel Roddis/EPA/Shutterstock

“Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge,” the insider reveals. “They were very careful about it and even sleuthy at times, although the small group of people who were on set with them every day eventually figured it out.”

Related: Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More

Although the Drinking Buddies star was engaged to Sudeikis, 45, last year, their relationship was “already done” before she moved on with the former One Direction frontman.

“Harry did not break up an engagement,” the source tells Us.

They’re not hiding anymore either. Wilde and Styles made headlines after photos of them holding hands at his manager Jeffrey Azoff’s wedding in Montecito, California, went viral on Monday, January 4. A source told Us after the nuptials that the “Sign of the Times” singer referred to Wilde as his “girlfriend” during his wedding speech.

The pair grew close while working on Wilde’s latest directorial project, Don’t Worry Darling. The film — a psychological thriller — also stars Florence Pugh and Chris Pine.

Wilde and Styles were spotted cozying up together while out for a walk in Santa Barbara, California, on Sunday, January 3. Photos published by the Daily Mail showed the “Fine Line” singer caressing Wilde’s waist while they strolled together.

Related: Stars Who Dated Their Directors: Harry Styles and More

The Grammy nominee wore a sweatshirt and pink beanie on the outing while the Booksmart director sported a cropped argyle sweater. Both wore masks to protect themselves and others amid the coronavirus pandemic.

Wilde was previously married to Tao Ruspoli from 2003 to 2011. She moved on with Sudeikis in November 2011. The exes got engaged a year later and welcomed two children, Otis, 6, and Daisy, 4, during their relationship. Us confirmed their split after nearly a decade together in November 2020.

“They’ve been separated for months now and there really is no drama. They’re handling this like adults,” an insider said of the duo when news of their split first broke. “It’s all about coparenting their kids, Daisy and Otis. That’s the priority for them.”

The source told Us there was occasionally tension between Wilde and Sudeikis over work matters.

“Of course, there were arguments and fights over career decisions and where to live. … She was also busier than him at times, which was difficult at times,” the insider said in November. “They butted heads on many occasions and decided it was best to go their separate ways. Bottom line: they had issues and they were never going to get married.”

With reporting by Nicholas Hautman

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