Olivia Wilde and Harry Styles Were “Very Careful” to Keep Their Relationship “Under Wraps”

When photographs of Harry Styles and Olivia Wilde holding hands hit the internet, it seemed as though the world was desperate to find out everything they could about the fledgling couple.

Here, we round up what we know so far about Harry Styles and Olivia Wilde’s relationship.

September 2020: Harry Styles is cast in Olivia Wilde’s new movie.

Deadline reports the news that Styles has replaced Shia LaBeouf in the forthcoming movie, Don’t Worry, Darling. Wilde serves as director on the project, with a script from Katie Silberman. The movie costars Chris Pine and Florence Pugh, with Wilde taking a small role, too.

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November 2020: Olivia Wilde describes her “victory dance” after casting Harry Styles.

Interviewed as part of Styles’s Vogue cover story, Wilde opens up about her reaction to casting the former One Direction member in Don’t Worry Darling. Wilde also describes the excitement she shares with Oscar-nominee, and the film’s costume designer, Arianne Phillips. “She and I did a little victory dance when we heard that we officially had Harry in the film, because we knew that he has a real appreciation for fashion and style,” Wilde explained (via People). “And this movie is incredibly stylistic. It’s very heightened and opulent, and I’m really grateful that he is so enthusiastic about that element of the process—some actors just don’t care.”

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“To me, he’s very modern, and I hope that this brand of confidence as a male that Harry has—truly devoid of any traces of toxic masculinity—is indicative of his generation and therefore the future of the world,” Wilde said. “I think he is in many ways championing that, spearheading that. It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.”

November 2020: Olivia Wilde splits from fiancé Jason Sudeikis.

In mid-November, news breaks of Olivia Wilde’s split from Jason Sudeikis, with People calling the breakup “amicable,” and noting the former couple’s dedication to their two children, son Otis Alexander, 6, and daughter Daisy Josephine, 4.

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A source told People, “The split happened at the beginning of the year… It’s been amicable and they’ve transitioned into a great coparenting routine. The children are the priority and the heart of the family’s relationship.” Entertainment Tonight appeared to confirm this narrative, with a source allegedly close to Wilde calling the split “mutual.”

“They just fell out of love in a romantic way, but still have love towards one another as people,” the source explained to ET. “They consider themselves friends and co-parents first and foremost.” Another source added, “there was absolutely no drama or scandal, they just didn’t work as a couple anymore. If you’re looking for a juicy story, there just isn’t one.”

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Wilde and Sudeikis were first romantically linked in November 2011, and Sudeikis proposed to Wilde just over a year later.

January 2021: Olivia Wilde holds hands with Harry Styles at a wedding.

In early 2021, photographs of Wilde and Styles holding hands surface online, and the internet erupts with questions. The new couple is spotted attending his agent’s wedding at the San Ysidro Ranch in Montecito, California.

An insider revealed to People that the new couple had been dating for some time. “They were in Montecito, California this weekend for a wedding,” a source told People. “They were affectionate around their friends, held hands and looked very happy. They have dated for a few weeks.” Twitter immediately mourns the fact that Styles is no longer a single man.

Meanwhile, a source revealed to Entertainment Tonight, that Wilde and Styles got to know each other on the set of Don’t Worry, Darling, and their romance blossomed from there. “Olivia and Harry are together for long days on set and have gotten to know each other really well, so it’s all very organic,” the source revealed. “[Olivia] wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully.”

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Further instances of PDA only seem to solidify their status as Hollywood’s newest power couple. A source also confirms to Us Weekly that Wilde and Styles worked hard to keep their relationship a secret during filming. “Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge,” Us Weekly‘s source revealed. “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.”

January 2020: Jason Sudeikis is subjected to conflicting reports.

It’s currently unclear how Wilde’s ex, Sudeikis, feels about her new relationship with Styles. A source claimed to ET that as Wilde and Sudeikis separated “almost a year ago… it’s not like she’s rushing into something.” The source continued, “Olivia and Jason talk all the time and are still close because of the kids. It’s highly unlikely he was blind-sided by this news.” Us Weekly‘s source concurs, saying, “Harry did not break up an engagement,” describing Wilde’s relationship with Sudeikis as “already done” by the time she met Styles.

However, People tells a very different story, with an insider claiming, “[Jason Sudeikis] is absolutely heartbroken about the split. There is still a lot of love there, and he would like to have hope that maybe there’s a way for them to repair things. But what happens next remains to be seen.”

Watch this space for further updates!

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