As a seasoned observer of Hollywood’s intricate web of relationships, I must admit that the tale of Olivia Wilde and her high-profile love life is as captivating as any blockbuster movie. The twists and turns in this narrative are enough to make even the most jaded Tinseltown resident sit up and take notice.
Harry Styles and Olivia Wilde are well-known figures in the world of Hollywood. Interestingly, they’ve both ventured into new territories that deviate from their initial fame. For instance, Harry Styles has stepped into the realm of acting, while Olivia Wilde has taken on the role of 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.
Ever since those whispers began to swirl, folks have been quick to notice the decade-long difference between us, with Harry being the younger one compared to me, Olivia Wilde. Yet, it seemed as if this age gap was never an obstacle in our budding relationship.
If you’re unsure about the specific sequence of events or simply curious about how Harry Styles and Olivia Wilde’s relationship developed following their professional collaboration, you’ve come to the right spot! Let’s delve into the chronology of their relationship.
September 2020: Olivia Wilde Casts Harry Styles in Don’t Worry Darling Film
It’s worth mentioning that in September, it was revealed that Harry Styles was joining Olivia Wilde’s directorial project titled “Don’t Worry Darling.” Initially, Shia LaBeouf had been slated for the role that eventually went to Harry Styles, who will be working alongside Florence Pugh.
According to Deadline’s report, due to complications with the filming schedule, Shia LaBeouf had to withdraw from the project, and the role was subsequently taken over by the singer.
November 2020: Olivia Wilde and her ex Jason Sudeikis’ split goes public
It’s been said that after a prolonged relationship, Olivia and Jason decided to part ways, having called off their engagement.
The former pair have two offspring – a son named Otis and a daughter called Daisy. According to a source, their separation took place early in the current year, with the children’s welfare being their top concern as reported to People Magazine.
January 2021: Harry Styles and Olivia Wilde spotted holding hands
There’s been lots of chatter online about whether Styles and Wilde might be dating. According to a report, they were seen together with their hands held at the wedding of the Watermelon Sugar singer’s agent in Montacito, California back in January 2021.
Online fans were taken aback by the charming photos of Harry and Olivia. A source revealed to the publication that they had been quite affectionate in public, often holding hands and displaying visible joy. The couple has reportedly been dating for a few weeks now.
February 2021: Olivia Wilde appreciates Harry Styles on social media
About a month following the spread of their photo online, she publicly acknowledged and commended the former One Direction member on her Instagram account. In a heartfelt post, she expressed her gratitude towards the artist.
Wilde posted a monochrome snapshot of Styles dressed in a suit, seated inside an antique black vehicle. Her acting contemporary penned, “Interesting tidbit: Many male actors express reluctance towards taking up supporting roles in movies headlined by women.”
The actress commented, “The industry instills in them the belief that taking these roles diminishes their worth (or financial value), which is one reason it’s tough to secure funding for films about women’s stories. It’s no exaggeration to say it can be challenging to find actors who understand why it could be beneficial for a woman to take center stage. Step in: @harrystyles, our ‘Jack.'”
The movie director additionally mentioned that Styles generously allowed Florence to showcase her skills independently, illuminating in her unique brilliance. In her own words, “He didn’t need to join our troupe, yet with humility and elegance, he embarked on this journey with us, astonishing us daily with his talent, kindness, and skillful driving in reverse.” Here’s the full caption for further reading: [Link to post]
October 2021: Olivia Wilde opens up about living in London
In the vibrant cityscape of London, last June, I found myself at the center of an intriguing story. The charismatic star of Tron: Legacy and the captivating X-Factor contestant were frequently spotted sharing meals or leisurely strolls, their hands intertwined. These sightings, a recurring theme, sparked whispers of a blossoming connection between these two captivating individuals.
That particular October, during an interview with Vogue Magazine, she shared that she had moved permanently to London.
Discussing her recent adventures, Wilde explained that she had taken the wheel of a car for the first time, as she no longer resides permanently in New York. Instead, she spends her time divided between Los Angeles and London.
The actress commented, “Driving has become something that makes me ponder about contributing positively to future advancements. Lately, I’ve been using an electric car, and it gives me the feeling of being a more compassionate person.”
April 2022: Olivia Wilde graces Coachella With Harry Styles
In 2022, the musician was the main act at Coachella, and the actress from Cowboys & Aliens attended to watch her partner perform. According to Billboard, Wilde was spotted in videos taken by festival-goers. She was seen encouraging Styles and later getting close during Billie Eilish’s set.
May 2022: Harry Styles tries to avoid answering questions about Olivia Wilde
In May, Harry Styles was a guest on Howard Stern’s radio show on SiriusXM. During the interview, Stern directly questioned Styles about falling in love on a film set by asking, “Did you fall in love while shooting a movie?”
In a roundabout manner, the singer chose not to directly address the query. Instead, he shared that collaborating with her was a memorable experience for him. Styles further commented, “I believe there’s something that clearly… acting can be quite unsettling at times. I think you have to rely heavily on trust.”
May 2022: Harry Styles releases Harry’s House
Since leaving One Direction behind, Harry Styles has thrived as a standalone musician. In the month of May 2022, he unveiled his third solo album, titled “Harry’s House.”
There’s been a lot of talk among the singer’s fans that several lyrics from the album might be referring to Wild. Some even believe that the song “As It Was” is hinting at her.
August 2022: Olivia Wilde and Harry Styles spotted in New York
During the brief run of shows at Madison Square Garden by the actor from Dunkirk, beginning in late August, they were frequently seen dining together and working out at the same gym on multiple occasions. Discussions about this couple continued to circulate online.
August 2022: CinemaCon controversy surrounding Olivia and ex Jason takes over
At the 2022 CinemaCon, she discussed her upcoming directorial project and mentioned her partner, whom she referred to as a “surprise.” She playfully quipped, “a rising star in acting, with no other profession I’ve heard of that I know of.”
According to Billboard, the evening became contentious when someone acting on behalf of her former fiancé handed her custody documents during her performance on stage.
August 2022: Harry and Olivia speak out about the hate their relationship received
Based on reports, in a Rolling Stone magazine feature published in 2022, Harry Styles and Olivia Wilde discussed experiencing online harassment, particularly from some members of his fan base.
As a devoted admirer, I’d put it like this: The vocalist confided that such an experience didn’t sit well with him. He went on to illustrate a hypothetical scenario: “Imagine, if you will, ending a first date and suggesting a second one, only to reveal that there’s a corner where they’ll say something outrageous, be unkind, and it’s all an act… It’s not genuine. Yet, I find myself asking, ‘So, what would you like 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 expressed, “I find it hard to comprehend the harshness you’re mentioning since such destructive negativity contradicts everything positive and embodied by Harry, as portrayed in his work.”
She went on to clarify that she doesn’t think the harmful attitude characterizes his fan base as a whole. Instead, she emphasized that most of them genuinely embody kindness.
August 2022: Olivia Wilde on keeping their relationship private
Simultaneously with Styles’s Rolling Stone feature, Wilde graced the cover of Variety as well.
In her chat with the media, she discussed why she and her partner opt for a private approach when it comes to their romantic life.
The actress mentioned that she wouldn’t comment on the matter since she believes no relationship thrives when exposed to the public eye. She further explained, “We make an effort to shield our relationship because we believe it’s beneficial and stemming from our past experiences as well as our profound affection for each other.”
September 2022: Don’t Worry Darling cast attends Venice Film Festive for its premiere
At the Venice Film Festival, the actors from Don’t Worry Darling walked the red carpet as a group. However, this particular event marked the first occasion that this specific duo stepped onto a red carpet side by side.
As a longtime fan of both Harry Styles and Chris Pine, I found myself deeply disappointed and saddened by the recent allegations that surfaced regarding their altercation during an event. Having followed their careers for years and admiring their talent, it’s disheartening to see such negative headlines associated with them. If this incident is indeed true, it tarnishes not only their professional reputations but also the positive image they have worked hard to maintain throughout their careers.
It was also rumored among many internet users that Florence Pugh, the main actress, might have had a disagreement or fallen out with Wilde.
September 2022: Olivia Wilde talks about being accused of cheating
It was rumored that Wilde may have ended her engagement with Jason and started dating Harry Styles, but these rumors gained more traction after the CinemaCon event. However, in an interview with Vanity Fair, she clarified, “The notion that I left Jason for Harry is entirely false.” She explained further that their relationship had already ended before she met Styles, and as she stated in her article, “Any relationship that ends doesn’t end overnight.”
During the lockdown, the actress mentioned she was caring for two children alongside her ex-partner. They found it necessary to co-parent during that time. However, it eventually became evident that living together wasn’t advantageous for their kids. Wilde expressed, “It was the responsible choice to no longer live together because we could be better parents as friends who reside in separate homes.”
September 2022: Olivia Wilde attends Harry’s MSG show
In September 2022, the actress who played on House TV series attended the concert of the singer known for Steal My Girl at Madison Square Garden. At this venue, he was given a special banner hanging from the rafters, commemorating his record-breaking Love on Tour event with 15 sold-out shows. Photos showed her cheering on her partner and enjoying the performance.
September 2022: Olivia Wilde elaborates on SpitGate
During her interview on The Late Show with Stephen Colbert, she discussed the viral video involving her boyfriend, known as ‘SpitGate’, which claimed that Harry Styles might have spat on Chris Pine at the Venice Film Festival.
Wilder pointed out that it was a flawless demonstration of how individuals seek out drama even in the most ordinary circumstances. To set the record straight, she emphasized that her boyfriend did not spit on Pine.
During our chat, she mentioned that she believed her male counterpart directors weren’t addressing queries regarding their actors.
As a film critic with years of experience under my belt, I’ve noticed a recurring pattern that has left me quite disheartened. Time and again, male directors who exhibit tyrannical behavior are showered with praise for their work. It seems as though their questionable conduct is often overlooked in favor of discussing the films themselves or the supposed greatness of their talent.
November 2022: Harry and Olivia reportedly decide to take a break
According to People’s report, following two years as a couple, they chose to pause their relationship temporarily. Several sources suggested that each person was concentrating on distinct personal priorities.
According to a close acquaintance, the couple has chosen to pursue separate paths due to differing commitments. This individual mentioned that both of them are dealing with challenging circumstances – he’s currently traveling overseas while she concentrates on her family and work in Los Angeles. The source emphasized that their decision was amicable. The friend also hinted at the couple facing various trials throughout their relationship, as reported by the media outlet.
February 2023: An insider reveals that the ex-pair are still “close friends”
A trustworthy source disclosed to the mentioned media outlet that they remain good friends. Notably, there is no lingering resentment between them, and furthermore, the actress has several upcoming directorial projects on her agenda.
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2024-08-06 19:53