Timeline of Harry Styles and Olivia Wilde’s Relationship

The first unexpected celebrity relationship of 2021, involving the 36-year-old Olivia Wilde and 26-year-old Harry Styles, emerged early in the year. While she was directing him in the upcoming movie Don’t Worry Darling, they became friends. After the celebrities were seen holding hands at his manager’s wedding in early 2021, several publications claimed that they were dating.

Harry Styles will be competing for the Grammy for Best Immersive Audio Album on Sunday, April 3. Following a delay brought on by a COVID-19 spike, the 2022 Grammy Awards are now being held in Las Vegas, Nevada. With his new song “As It Was,” the musician just set streaming records. After spending more than a year together, it seems sense for Wilde to be by Styles’ side in this important moment.

After nine years and two children—Otis, 7, and Daisy, 4—with her longtime partner Jason Sudeikis, Wilde and the couple started dating off-screen. Harry Styles’ love life before meeting Olivia Wilde, according to the source, was “basically nonexistent during lockdown.” Consider his lack of dates to be over. The following information about Styles and Wilde’s relationship includes information on their on-screen encounter and their spring and summer in London.

The casting for Don’t Worry Darling, Wilde’s follow-up to his 2019 film Booksmart, was announced. Shia LaBeouf was apparently replaced by Styles because of his “bad behavior” and breach of Wilde’s “zero asshole policy” on set, according to a source who spoke to Variety. Although early reports said that LaBeouf’s departure was due to a schedule dispute, his departure also coincided with the filing of a lawsuit by his ex-girlfriend FKA twigs accusing him of “sexual violence, assault, and infliction of emotional distress.”

Wilde announced Styles and Florence Pugh’s casting on Instagram, writing, “Jack and Alice. Very proud to work with these fine folks. #DontWorryDarling.”

Harry Styles

October 15

Filming began in mid-October with Wilde posting a photo of the Don’t Worry Darling director’s slate. Blank slate. Full heart. Let’s do the damn thing, @libatique. 💪 #pressureisaprivilege,” she captioned the post.

November 13, 2020

For his cover interview with Vogue, Olivia Wilde first discussed Harry Styles in public. “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 in the profile. “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.”

She also spoke about the moment she and the film’s costume designer, Arianne Phillips, found out Styles would be joining the cast. “She [Arianne] 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 told the outlet. “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.”

If those weren’t ringing endorsements enough, Wilde also defended Styles’s gown on the cover against conservative commentator Candace Owens. After Owens said, in part, “Bring back manly men,” Olivia Wilde replied, “You’re pathetic.”

On November 11, Wilde and Styles were spotted working out together in Los Angeles. Wilde was dressed for the gym in a black cropped tank top, matching black leggings, and black sneakers. Styles was wearing a more vibrant ensemble that included a blue blouse, black shorts, a green dufflebag, and patterned socks. The musician has recently recovered from the virus that decimated his band and caused him to postpone three shows.

The sold-out events were slated to take place on November 5, 6, and 7 at the Kia Forum in Inglewood. They were subsequently moved to January. He announced the news in an Instagram Story, saying he was “devastated.”

Towards the end of the show on Wednesday I started feeling ill and I’ve been in bed with the flu ever since,” Styles said. “I’ve been doing everything I can to be able to sing tonight, but I’m leaving the doctor now and I’m devastated that it’s just not possible. Until very recently I haven’t had to postpone a show due to illness in the 12 years I’ve been touring. I’m so sorry to do it, and if there was anyway I could do the show I would.”

He added, “I’m sorry this news is coming so close to show time, but it was my sincerest hope to be able to play for you tonight. I know several of you have planned trips to LA to see the show, and it means the absolute world to me.”

Early in October, Styles’ performance in Chicago was postponed owing to illness among the band and crew. A month later, it looks to have finally made it to the star.

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