Harry Styles broke hearts across the world when it was revealed he’d been dating actor slash filmmaker Olivia Wilde on the down-low. The pair met on the set of Don’t Worry Darling towards the end of 2020 and have since been spotted in a string of PDAs.
Olivia (38) previously dated Jason Sudeikis for nine years, and the pair share two children, eight-year-old Otis and five-year-old Daisy. Harry (28), who has dated the likes of Kendall Jenner and Taylor Swift, hasn’t publicly been romantically linked to anyone since he dated Camille Rowe in 2018.
Here’s a look back at Harry and Olivia’s dating history, starting with the most recent update:
August, 2022: Harry and Olivia give their first joint interview to Rolling Stone UK, and open up about everything from ‘online cruelty’ about their relationship to his overwhelming fan base.
When asked about the ‘small, toxic corners of the internet’ that sometimes treat his loved ones poorly, Harry said, “That obviously doesn’t make me feel good. It’s obviously a difficult feeling to feel like being close to me means you’re at the ransom of a corner of Twitter or something. I just wanted to sing, I didn’t want to get into it if I was going to hurt people like that.”
Olivia then insisted that despite this, the majority of Harry’s fanbase have good intentions, continuing, “What I don’t understand about the cruelty you’re referencing is that that kind of toxic negativity is the antithesis of Harry, and everything he puts out there. I don’t personally believe the hateful energy defines his fan base at all, the majority of them are true champions of kindness.”
Here’s the rest of Harry Styles and Olivia Wilde’s timeline…
September 11, 2020: It’s announced that Harry has been cast alongside Florence Pugh in the upcoming movie Don’t Worry Darling, directed by Olivia. Harry reportedly replaced Shia LaBeouf after his “poor behaviour” on set (via Variety).
Olivia confirmed the casting with a post to her Instagram, captioned: “Jack and Alice. Very proud to work with these fine folks #DontWorryDarling”
October 15, 2020: Olivia celebrates the start of filming for Don’t Worry Darling with an Instagram post. “Blank slate. Full heart. Let’s do the damn thing, @libatique đź’Ş #pressureisaprivilege” she wrote.
November 13, 2020: Olivia speaks publicly about Harry for the first time in an interview with Vogue, and she certainly had plenty of positive things to say about him.
“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.
She continued, “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.”
Olivia also spoke about how excited she and Don’t Worry Darling’s costume designer were to have Harry onboard for the film. “She [the costume designer] 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,” she said. “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.”
November 16, 2020: Olivia claps back at a Twitter user trolling Harry’s outfit choices. “There is no society that can survive without strong men. The East knows this. In the West, the steady feminisation of our men at the same time that Marxism is being taught to our children is not a coincidence. It is an outright attack. Bring back manly men,” tweeted author Candace Owens in response to a photo of Harry in a dress.
Olivia simply replied “You’re pathetic.”
Yes Olivia! đź‘Źđź‘Źđź‘Ź
January 4, 2021: Harry and Olivia’s relationship is all but confirmed after photos emerged of the pair holding hands at his manager’s wedding. See the pics here.
At the same time, a source revealed to People that the couple had been dating “for a few weeks,” adding that at the wedding they “were affectionate around their friends, held hands and looked very happy.”
Another source, who spoke to The Sun, said they had “clicked immediately.”
“It was one of those things where straight away everyone could see they had a spark,” The Sun’s source added, “it’s no surprise something has happened, but now they’re quite open about it and out and about as a couple.”
Meanwhile, a source spoke to Entertainment Tonight about suggestions that Olivia had moved on too quickly from Jason Sudeikis after their breakup. The source said the long-term couple had split early in 2020, but didn’t announce the news until November. “Olivia and Jason talk all the time and are still close because of the kids,” the source added, “it’s highly unlikely he was blind-sided by this news.”
January 5, 2021: A source tells Page Six that Harry referred to Olivia as his “girlfriend” during a speech at the wedding. The source also revealed James Corden set the pair up after they both stayed at his California home while filming their movie.
“Harry had been staying at James Corden’s house near Palm Springs during filming, and so they were able to be alone and keep their relationship very secret,” the source said. “So everyone was really surprised—and rather delighted—when Harry brought Olivia as his date to the wedding, and introduced her as his girlfriend.”
January 7, 2021: The new couple are spotted out together for the second time – Harry had his arm around Olivia as they strolled around Santa Barbara.
January 8, 2021: Although Entertainment Tonight reported Olivia and Jason “fell out of love in a romantic way” and that there was “absolutely no drama or scandal”, a source told People that after Olivia’s relationship with Harry was made public, Jason was “heartbroken.”
The source added, “There is still a lot of love there, and he [Jason] would like to have hoped that maybe there’s a way for them to repair things. But what happens next remains to be seen.”
January 10, 2021: Yet another conflicting story about the timeline of Olivia and Harry’s relationship vs Olivia and Jason’s breakup is reported. Speaking to US Weekly, a source said: “Olivia called off the engagement in early November but only after she already had gotten close to Harry.
“Whether Harry knows it or not, he was a reason for the split and it blindsided Jason—he totally adores Olivia and is devastated. Family is his biggest priority,” the source added.
February 14, 2021: Olivia shares a sweet Valentine’s Day tribute to Harry on her Instagram. “He didn’t have to join our circus,” Olivia wrote in the caption, “but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards. đź‘Š”
February 17, 2021: E! reports that Harry and Olivia have travelled to London together after wrapping up filming for Don’t Worry Darling. “Harry and Olivia loved being on the road and have gotten very comfortable spending all of their time together,” a source told E! “They are rarely apart and it made sense to go to London together.”
April 14, 2021: The couple are spotted together for the first time in two months at a pub in London. An onlooker told The Mirror: “They looked very cozy on an intimate table for two away from other diners. They were grinning like Cheshire cats at each other all night.”
“[Olivia] had her legs crossed and gently nudged against him,” the source added, “they looked completely smitten.”
April 21, 2021: A source tells Entertainment Tonight that the couple have been spending time out of the spotlight and enjoying some alone time. “Filming during a pandemic in LA was pretty all-consuming,” the source said. “Now they’re able to unwind, relax and really enjoy some one-on-one time.”
June 4, 2021: The couple continue to spend time together in London while Harry films The Policeman. Speaking about their time in the capital, a source told Entertainment Tonight, “[they’ve] been going on walks outside in the park and not hiding their relationship [and have] grown even closer as a couple.”
July 5, 2021: Harry and Olivia packed on some *major* PDA while on a yacht in Italy. The couple clearly couldn’t keep their hands off each other as they cuddled up on deck and even appeared to share a dance. How romantic.
See the pics here.
A source close to Harry told Page Six: “Harry has been seen taking a break on the beach in Porto Ercole after he finished filming My Policeman in London.”
“Olivia has also been in London, spending time with her kids, who are there with Jason,” the source added, “Olivia stayed behind with her kids, then she flew into Porto Ercole to join Harry.”
10 December, 2021: In a cover interview for Vogue US, Olivia opened up about her relationship with Harry, revealing that she’s “happier” than she’s ever been. Because of that, she says she’s no longer interested in what the press or the public have to say about their romance – particularly when it comes to their ten year age gap.
“It’s obviously really tempting to correct a false narrative,” she said. “But I think what you realise is that when you’re really happy, it doesn’t matter what strangers think about you. All that matters to you is what’s real, and what you love, and who you love.”
We couldn’t have said it better ourselves!
March, 2022: Harry and Olivia are spotted holding hands in London’s Soho, in a rare show of public affection. In photos obtained by Metro, the singer wore Vans with ripped blue jeans, a white t-shirt and a bag from his Pleasing makeup line, while Olivia wore a white shirt under a blue jumper and black kick flare trousers.
What a stylish couple.
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