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Harry Styles and Olivia Wilde Relationship Timeline: Exploring Couple’s Journey Amid Multiple Controversies
Here’s a close look at Harry Styles and Olivia Wilde’s relationship timeline. Read ahead to get an insight into their romance
Harry Styles and Olivia Wilde are big names in Hollywood. Both individuals have delved into different roles than what they have been known for. Styles' career branched out to acting and Wilde’s career expanded as a director.
It came as a surprise to everyone when the speculation about both individuals seeing each other started swirling over the internet. Wilde, who was previously engaged to actor Jason Sudeikis was heavily being talked about because soon after her split with Jason, news about her and Styles' relationship started making rounds.
After the rumors started circulating, many people pointed out their 10-year age gap, as Wilde is a decade older than Styles. But it appeared that this was not a problem for the couple.
In case you are confused about the exact timeline or maybe just want to know about their relationship blossoming after working with each other professionally, you are at the right place. Here’s a look at Harry Styles and Olivia Wilde’s relationship timeline.
September 2020: Olivia Wilde Casts Harry Styles in Don't Worry Darling Film
In September, Harry Styles was announced to be a part of Olivia Wilde’s directorial, Dont Worry Darling. Although Harry was cast in the film, earlier, Shia LaBeouf was supposed to play Style’s role opposite Florence Pugh.
As per Deadline, because of scheduling issues, Shia had to say goodbye to the movie and the singer replaced him.
November 2020: Olivia Wilde and her ex Jason Sudeikis' split goes public
People reported that Olivia and Jason put an end to their longtime romance. They broke their engagement and went on their separate ways.
The ex-couple shares two children, a son Otis, and a daughter Daisy. An insider reported to People Magazine that the split occurred at the start of that year and their kids's well-being was their main priority.
January 2021: Harry Styles and Olivia Wilde spotted holding hands
Both Styles and Wilde were being talked on the internet for being in a rumored relationship. As per the outlet, they were spotted holding hands at the Watermelon Sugar vocalist’s agent’s wedding in Montacito, California in January 2021.
Harry’s and Olivia’s pictures surprised their fans online. An insider told the outlet, “They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks.”
February 2021: Olivia Wilde appreciates Harry Styles on social media
A month after the couple’s picture went viral, she openly praised the One Direction alum on her Instagram handle. She wrote a lengthy cation appreciating the singer.
Wilde shared a black and white photo of Styles wearing a suit as he sat in a black vintage car. Her actress wrote, “Little known fact: Most male actors don't want to play supporting roles in female-led films.”
The actress added, “The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it's so hard to get financing for movies focusing on female stories. No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight. Enter: @harrystyles, our 'Jack.'”
The film director also stated that Styles gave his co-star Florence a space to “shine in her own light.” She wrote, “He didn't have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards.” Check out the post below and read the entire caption.
October 2021: Olivia Wilde opens up about living in London
As per Billboard, in June of 2021, the Tron: Legacy star along with the X-factor contestant were spotted holding hands having lunch, or taking a stroll together in London. The spotting was recurring on multiple occasions.
In October of that year, while speaking with Vogue Magazine, she stated that she was officially living in London.
Talking about her experience, Wilde stated that she was finally driving a car. She clarified that she lived in New York so she did not need a car but she did not live there anymore as she was living between Los Angeles and London.
The actress added, “Driving is now a thing where I’m like, ‘How am I going to participate in future innovation in a good way?’ I’ve been driving an electric car. And I’m like, ‘Ah, this does make me feel like a better human being.'”
April 2022: Olivia Wilde graces Coachella With Harry Styles
In 2022, the singer was headlining Coachella and the Cowboys & Aliens actress graced the event to watch her beau perform. As per Billboard, Wilde was seen in videos captured by the festival attendees. She was seen cheering for Styles and later getting cozy during Billie Eilish’s performance.
May 2022: Harry Styles tries to avoid answering questions about Olivia Wilde
In May, Styles appeared on Howard Stern's SiriusXM radio show, during which the host bluntly asked Styles, “You fell in love on a movie set?”
Which, the singer tried to avoid straightforwardly answering this question. Instead, he said that he had a wonderful experience working with her. Styles added, “I think there is something that obviously … acting is very uncomfortable at times. I think you have to trust a lot.”
May 2022: Harry Styles releases Harry’s House
After his departure from One Direction, Styles has been successful as a solo artist. In May of 2022, his third studio album, Harry’s House was released.
Many fans of the singer started speculating that multiple lyrics of the songs included in the album were rumored to be about Wild. Many speculated As It Was is allegedly about her.
August 2022: Olivia Wilde and Harry Styles spotted in New York
During the Dunkirk star’s Madison Square Garden mini-residency, which started in late August, they were spotted on several occasions, having dinner and hitting the gym together. The conversations surrounding the pair were still talked about online.
August 2022: CinemaCon controversy surrounding Olivia and ex Jason takes over
During the 2022 CinemaCon, she conversed about her directorial venture. She also spoke about her beau, referring to him as a “revelation.” She joked, “an up-and-coming actor with no other career that I’m aware of.”
As per Billboard, the night turned controversial as a proxy on behalf of her ex-fiance served her with custody papers while she was on stage.
August 2022: Harry and Olivia speak out about the hate their relationship received
According to the outlet, in 2022, In Styles’s Rolling Stone cover story, the As It Was singer and Wilde spoke about receiving hate online, especially from a section of Styles’s fanbase.
The vocalist stated that it did not make him feel good. He added, “Can you imagine going on a second date with someone and being like, ‘OK, there’s this corner of the thing, and they’re going to say this, and it’s going to be really crazy, and they’re going to be really mean, and it’s not real. … But anyway, what do you want to eat?’"
He continued that it was a difficult feeling, being close to him meant that person was at the “ransom of a corner of Twitter or something.”
The director-actress stated, "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."
She added that she did not personally believe the hateful energy defines his fan base at all. She continued, “The majority of them are true champions of kindness.”
August 2022: Olivia Wilde on keeping their relationship private
During the same time as Styles’s Rolling Stone cover story, Wilde also appeared in her own cover story for Variety.
During her conversation with the outlet, she touched on the reason she and her beau prefer to stay low-key with their relationship.
The actress shared that she was not going to say anything about it as she had never seen a relationship benefit from being dragged into public space. She added, “We both go out of our way to protect our relationship; I think it’s out of experience, but also just out of deep love.”
September 2022: Don’t Worry Darling cast attends Venice Film Festive for its premiere
The cast of Dont Worry Darling appeared on the red carpet of the Venice Film Festival. Although it was with the ensemble cast, this was the first time the pair made their entry together on a red carpet.
This failed to catch the eye as the video of Harry Styles allegedly spitting on his co-star Chris Pine during the event went viral. The internet was heavily speaking about this controversy.
Many people online also speculated that the lead actress, Florence Pugh also had a falling out with Wilde.
September 2022: Olivia Wilde talks about being accused of cheating
It was speculated that Wilde allegedly left her ex-fiance for Styles, but the speculation elevated especially after the CinemaCon event. In her Vanity Fair cover story, she stated, “The complete horses**t idea that I left Jason for Harry is completely inaccurate,” adding that their relationship was long over before she met the singer. Wide contained, "Like any relationship that ends, it doesn’t end overnight.”
The actress also shared that they were raising two children during the lockdown, so they co-parented during that time. It became clear to the former couple that living with each other was not beneficial for their kids. Wilde stated, “It became the responsible thing to not because we could be better parents as friends who live in different houses.”
September 2022: Olivia Wilde attends Harry’s MSG show
In September of 2022, the House actress attended the Steal My Girl singer’s Madison Square Garden concert. There, he was greeted with a unique banner that hung from the rafters at the venue, honoring his historic Love on Tour engagement, which consisted of 15 sold-out shows. She was seen supporting her beau and enjoying the show.
September 2022: Olivia Wilde elaborates on SpitGate
During Wilde’s appearance on The Late Show With Stephen Colbert, she touched up on her beau’s ‘SpitGate’ video that was making rounds on the internet. The video was about Styles allegedly spitting on Pine during the Venice Film Festival.
Wilde stated that it was a perfect example of how people will look for drama anywhere. She clarified that her beau did not spit on Pine.
While conversing with the host, she also stated that she did not think that her male director colleagues were answering questions about their cast.
She added, “ (Male directors) are praised for being tyrannical. They can be investigated time and time again. It doesn’t overtake conversations about their actual talent or the films themselves.”
November 2022: Harry and Olivia reportedly decide to take a break
As reported by People, after two years of being together, the couple decided to take a break. Multiple insiders claimed that both individuals were focusing on different priorities.
A source said, “He's still touring and is now going abroad. She is focusing on her kids and her work in L.A. It's a very amicable decision.” A friend of the couple stated that they had different priorities that were keeping them away. They added that the public pressure on the couple was hard and they have had their “ups and downs throughout their relationship,” per the outlet.
February 2023: An insider reveals that the ex-pair are still “close friends”
An insider told the aforementioned publication, “They're still very close friends.” The source added that there was no “animosity” and adding to that the actress had multiple directing ventures in the works.
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