Harry Styles and Olivia Wilde's Unexpected Romance: Everything We Know

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Harry Styles and Olivia Wilde are the hottest new Hollywood couple!

Wilde, 36, is currently directing the "Golden" singer, 27, in her upcoming psychological thriller, Don't Worry Darling, and many people were surprised to find out that the two had sparked a romance.

While Styles has been single for quite some time, the actress-turned-director just got out of a nine-year engagement with Jason Sudeikis last year. They share two children together.

But despite both being unattached, Styles and Wilde fans were nevertheless shocked when the two were snapped holding hands at a wedding in early January. The two have yet to speak out on their romance, but there's plenty of photos to prove that they are totally into one another.

As this romance continues to heat up, here is everything we know about Styles and Wilde’s unexpected fling.

The Start of It All

Styles and Wilde were first professionally linked in September 2020. At that time, it was announced that the singer was replacing Shia LaBeouf in her upcoming film, which centers on an unhappy housewife in the 1950s. Wilde told Vogue in November, she did a "happy dance" upon confirming Styles’ involvement in Don’t Worry Darling after LaBeouf exited due to scheduling conflicts. 

"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," she said of the former One Direction member. "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."

That same Vogue feature included Styles wearing a dress and making history as the magazine’s first-ever male cover star. The singer received some criticism for his feminine attire, with conservative commentator Candace Owens tweeting in part, "Bring back manly men."

Wilde came to her star’s defense, simply replying to Owens, “You’re pathetic.”

Romance Rumors and First Photos Together

On Jan. 4, photographs of the two holding hands at a wedding together surfaced online. That day, ET learned that the pair attended the nuptials of Styles' manager, Jeffrey Azoff. In pictures published by Page Six, Wilde looked stunning in a floral long-sleeved maxi dress and a pink headband, while Styles was stylish as ever in a wide-legged black suit.

The "Adore You" crooner was also snapped in his bathrobe at one point, happily posing with Azoff and his bride, Glenne Christiaansen. A source told ET that Styles officiated the wedding.

That same day, Wilde and Styles were photographed arriving back at his home in Los Angeles with their luggage, in pictures published by The Daily Mail. A couple of days later, new photos surfaced of the two getting cozy while out in Santa Barbara with friends.

Sparks Fly on Set

A source told ET that the two were growing close while working together on the set of Don't Worry Darling.

"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 told ET, adding that Wilde "wouldn't let a romantic relationship get in the way of a professional one, so anything they're doing is being done thoughtfully."

A second source told ET, "Olivia and Harry got close through working together on Don't Worry Darling. Since her split from Jason, she has been more open to seeing new people. She's always liked Harry and it was one of the reasons she cast him and, since then, she's developed a thing for him."

Meanwhile, a source told People their friendship "quickly turned romantic,” adding that "their chemistry was very obvious" and they had been dating for “a few weeks."

"During breaks in filming he wasn't able to stay away and would visit her trailer," the insider noted. Styles was photographed stopping by Wilde’s trailer on set on Nov. 3. 

Olivia Munn Harry Styles

Additionally, their 9-year age difference isn't a big deal for Styles, who has been known to date older women. "Clearly they’re enjoying themselves and the age gap really isn’t a thing. Harry has obviously famously had a thing for older women but he’s just extremely mature himself, you’d never think there was a decade between them," a source told The Sun.

Already a Little Bit of Drama

It appears as though the Booksmart helmer's former flame has his thoughts about her new beau.

While Wilde and Sudeikis wanted to remain close after their split, a source told ET that the Ted Lasso star is "really hurt" by Wilde's new romance with Styles.

"Olivia and Jason ended amicably and both wanted to remain close and stay friends for the sake of their kids and because they have mutual respect and love for one another," ET's source said, explaining that Sudeikis had hoped he and Wilde "would eventually reconcile and get back together." "He has been really hurt and somewhat jealous that Olivia has moved on with Harry," the sourced added. 

Another source told ET that the former Saturday Night Live comedian was "beyond distraught" to see Wilde move on, claiming he"still has feelings for [Olivia]."

Back to Work

As things heat up between Wilde and Styles, the two were photographed separately back on the set of their film on Jan. 29. In photos shared by People, Styles wore blue slacks with a white button-up, while Wilde rocked white sweats and a corduroy vest.

For more on this new relationship, watch the video below.


How Harry Styles and Olivia Wilde are Balancing Work and Romance

Harry Styles' Romance History and What He's Said About Dating

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