Harry Styles' rumoured romance with Olivia Wilde fascinated his fans, since they were first seen holding hands at a wedding in January 2021. They were later spotted on rare date nights, holidaying together and, of course, appearing in 2022 psychological thriller Don't Worry Darling, after director Wilde cast the former One Direction band member in the movie.
After seemingly becoming a fully-fledged couple, who've even got the same stylist (Karla Welch) and started dressing alike, the couple have reportedly split. But, there's speculation that the International mortal of affection Styles and all-round cool girl actor Olivia Wilde - known to fiercely protect their private life - are still very much fond of each other.
So, is a reunion on the cards? For the time being, we'll watch this space.
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Here's what we know:
21/11/22: 'There is no bad blood between' Olivia Wilde and Harry Styles following their rumoured break-up
In November 2022, news surfaced about Olivia Wilde and Harry Styles' rumoured break-up, after nearly two years of dating, but the pair are understood to still be on good terms.
A source told Page Six: 'There is no bad blood between them. Harry didn’t dump Olivia, or vice versa.'
They added: 'This is the longest relationship Harry’s ever had, so clearly they have a special bond.'
The Don't Worry Darling co-stars are believed to have conflicting schedules, which often means they are in different places and find it tricky to stay in contact.
'They’re on a break. It’s impossible to have a relationship when he’s in every continent next year and Olivia has her job and her kids,' the source elaborated.
'This is the right thing for both of them.'
While they pair have seemingly split, 'they’re friends, you’ll still see them together', according to the source.
A separate insider shared: 'Things have been challenging for them as a couple because of Harry’s tour, while Olivia needs to spend time with her kids in London, where they are with Jason [Sudeikis].'
When news of their split surfaced on Friday, a source told People: 'He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A., and added: 'It’s a very amicable decision. They’re still very close friends.'
23/09/22: Olivia Wilde and Harry Styles attend Don't Worry Darling premiere in sophisticated looks
Wilde and Styles made attended the premiere of Don't Worry Darling in New York City, and they dressed smartly in complementing looks.
For the glamorous occasion Wilde wore an elegant long black gown wit puff sleeves and styles donned a head-to-toe Gucci look, comprising a velvet double-breasted jacket, a blue oxford shirt, and wide-leg striped trousers.
Following the premiere, the two were seen heading to the after party together.
25/08/22: Olivia Wilde says she and Harry Styles 'go out of our way' to protect their relationship
Wilde spoke about the lengths she and Harry styles go to in order to protect the privacy.
In an interview with Variety, Wilde insisted that she wouldn't 'say anything about' her relationship with Styles 'because I've never seen a relationship benefit from being dragged into the public arena'.
She then spoke about working with the singer/actor on her upcoming film Don't Worry Darling, where they first met.
Wilde told the news outlet: '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.'
While she didn't specifically discuss Styles any further, she said: 'The whole culture of celebrity gossip is interesting as a distraction tool to numb people from the greater pains of the world.'
She continued: 'Escapism is really a very human quality, searching for something to anaesthetise the painful reality of so many people's lives.
'I don't blame people for seeking escapism, but I think the tabloid media is a tool to pit women against one another and to shame them.'
The actor and director said the last two years of her personal life were a 'restructuring and a revolution that should be a totally personal experience'. She added: 'And it's not.'
22/08/22: Harry Styles and Olivia Wilde discuss fan criticism and fascination of their relationship
Harry Styles has given rare insight into his fans' relationship with his partner Olivia Wilde.
In a new interview with Rolling Stone magazine, the 28-year-old singer opened up about compartmentalising discussions about his private and public life.
'I’ve never talked about my life away from work publicly and found that it’s benefited me positively,' he told the magazine. 'There’s always going to be a version of a narrative, and I think I just decided I wasn’t going to spend the time trying to correct it or redirect it in some way.'
In response to his fans' fascination with his relationship with Wilde, which includes some Twitter users criticising their 10-year age difference, he noted: '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.'
Wilde was also interviewed for Styles' profile interview and while she called her partner's fans 'deeply loving people', she added: '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.'
18/08/22: Harry Styles and Olivia Wilde are pictured on a rare date night in New York City
Harry Styles and Olivia Wilde were spotted on a rare date night in New York City on August 18.
They reportedly started off the day with a gym session together, which later saw them share a sweet kiss before heading to dinner.
Styles and Wilde were seen leaving Rubirosa in SoHo, with the latter dressed in a navy T-shirt and flowing midi skirt in white-and-blue toile de Jouy, which she grounded with adidas trainers.
She wore her hair down in an effortless tousled style and accessorised simply with a delicate necklace.
Styles, meanwhile, opted for a crochet knit layered over pinstriped tailored trousers and white trainers.
13/06/22: Harry Styles alludes to how he felt on meeting partner Olivia Wilde for the first time
During an interview on the Spout podcast Styles opened up about the inspiration behind his hit single 'Cinema'.
'I think it’s, like, when you like someone, that initial phase. "Am I doing things right?" Before you get comfortable with each other and it’s kinda, like, all of that stuff happens at the start of something,' he said.
When host Tamara Dhia suggested that no one was 'too cool' for Styles, he replied: 'We are all human.'
The quote came days before the singer played a concert in his hometown of Manchester and paused the show to locate his school teacher.
'I just want to thank you for everything in those formative years. Thank you so much,' he told his teacher, Mrs Vernon, after fans found her in the crowd and her face beamed on the screens at the Emirates Old Trafford Stadium.
'It means a lot to me that’s you’re here tonight, you were truly a wonderful teacher. Thank you from the bottom of my heart and it means a lot that you’re here and I’m dedicating this next song to you.'
19/05/22: Harry Styles responds to a question about falling 'in love' with Olivia Wilde on the set of Don't Worry Darling
In an interview with Howard Stern for the presenter's SiriusXM show on Wednesday May 18, Styles opened about what it was liking working with Wilde on their movie Don't Worry Darling.
Styles was asked: 'You fell in love on a movie set?', before the former One Direction band member replied: 'Oh, wow, how to answer this question?'
He continued: 'I had a wonderful experience being directed by Olivia. I think there is something that obviously … acting is very uncomfortable at times. I think you have to trust a lot.'
In reference to Wilde, Styles went on to say: 'Being able to trust your director is a gift.
'That was very helpful, and it really meant for a really nice experience working on that movie.'
This followed on from them being spotted out in Italy together the previous week.
10/05/22: Harry Styles opens up about the power of therapy
In an interview with Better Homes & Gardens, Styles candidly opened up about coping with his emotions, explaining that he started therapy about five years ago.
Admitting his previous perplexed feelings about seeking help for his mental health, he said: 'I thought it meant that you were broken. I wanted to be the one who could say I didn't need it.'
The 'As It Was' singer has clearly since found solace in attending therapy, as he told the publication it's helped him to 'open up rooms' in himself that he wasn't aware he had.
He added that it's enabled him to feel things more freely after 'emotionally coast[ing]' through life before'.
Seemingly, Styles' healthier approach to handling his emotions helps when it comes to having an open and honest relationship with rumoured fiancé Olivia Wilde.
He continued: 'I think that accepting living, being happy, hurting in the extremes, that is the most alive you can be. Losing it crying, losing it laughing—there's no way, I don't think, to feel more alive than that.'
27/04/22: Harry Styles discusses labels and sex shame
Styles has opened up about his sexuality and the intense public scrutiny over his sex life in recent years.
Since launching to fame with One Direction as a teenager, the ‘As It Was’ singer has been romantically linked to several famous women including Taylor Swift and Kendall Jenner. Last year the 28-year-old began dating actor Wilde, with the pair being spotted on numerous dates in the last year both in the US and UK.
However, in an interview, the former Coachella 2022 headliner said he felt ashamed for many years over the public knowing so much about his sex life.
‘For a long time, it felt like the only thing that was mine was my sex life. I felt so ashamed about it, ashamed at the idea of people even knowing that I was having sex, let alone who with,’ he told Better Homes & Gardens.
‘At the time, there were still the kiss-and-tell things. Working out who I could trust was stressful.
‘But I think I got to a place where I was like, why do I feel ashamed? I’m a 26-year-old man who’s single; it’s like, “yes, I have sex”.’
The now 28-year-old also discussed labels and why he’s chosen to be ‘really open’ about his with friends following years of speculation over his sexuality.
‘That’s my personal experience; it’s mine,’ he said, adding that he is focussed on moving towards a place of ‘accepting everybody’ and not caring to ‘clarify what boxes you’re checking’.
21/04/22: Harry Styles and Olivia Wilde Are Rumoured To Be Engaged
A few days after Harry Styles' headline Coachella performance, rumours of an engagement started swirling – all thanks to an Instagram Q&A with celebrity gossip account Deuxmoi. It's important to note that the account’s bio states that it 'does not claim any information published is based in fact' – but there have been numerous instances of Deuxmoi's claims being scarily on the money.
When asked by a follower during a Q&A session whether Harry and Olivia were 'really engaged', Deuxmoi responded: 'I think there is a high probability that they are. I’ve been saying for literal months that they are VERY serious and no one ever wants to believe me.'
Neither Harry nor Olivia has come out to comment on the rumours yet, but as you can imagine, the internet has already gone into overdrive.
Only time will tell...
7/2/22: Harry Styles And Olivia Wilde Went On A Museum Date For His Birthday
Styles reportedly celebrated his 28th birthday on February 1 with a London outing with Wilde.
They were seen at the Royal Academy of Arts, a couple of days after Styles' birthday, viewing the Francis Bacon: Man and Beast exhibition.
Fans spotted the couple, dressed casually and wearing face masks, with one later telling the Daily Mail: 'Harry and Olivia looked like they were having lots of fun as they browsed the gallery.
'Only a few One Direction fans noticed that Harry was around, so they mostly remained undisturbed....They didn't hold hands, but you could still see their closeness as they admired the art together.'
Wilde went on to share a post about the pair's visit via her Instagram stories.
Encouraging others to visit, she wrote: 'Francis Bacon at Royal Academy if you're in London go, go, go. [sic]'
The actor also showed us a glimpse into Styles' birthday dinner party at St John's Bread and Wine near London's Spitalfields Market.
She shared a photo of herself on Instagram standing by a candle-lit and flower-decorated table, accompanied by a message that read: 'Happy, happy. [sic]'
22/12/21: Harry Styles Is Reportedly Getting To Know Olivia Wilde's Kids
Ahead of Harry Styles and Olivia Wilde's apparent one-year anniversary, a source told People: 'Harry is slowly getting to know her kids.'
The source added: 'Olivia is also spending time with Harry's mum.'
In the midst of the pair's busy schedules, it has also been said that they aren't letting that get in the way of trying 'to see each other as much as possible'.
The same news outlet reported that Wilde had been constantly flying to and from LA, where her kids live, to join Styles on tour.
16/11/21: Harry Styles explains why he doesn't talk about his love life
In an interview with Dazed the Pleasing entrepreneur explained why he doesn't discuss his romances.
'I’ve always tried to compartmentalise my personal life and my working life,' he told the publication.
The star has been romantically linked to several women in the public eye including Kendall Jenner and Taylor Swift.
The comments come months after Style and Wilde sparked relationship rumours and have since been spotted on numerous occasions together.
06/09/21: Olivia Wilde appears backstage at Harry Styles' concert
On Saturday, September 4 the actor was seen hanging out backstage at Style's 'Golden' concert in Sin City.
For the occasion, the star wore a baby blue suit and face mask and was filmed in footage, shared on Twitter user Genna Baker's account, being directed to her seat.
07/07/21: Harry Styles and Olivia Wilde photographed on holiday together
Styles and Wilde's relationship appeared to be going from strength to strength, judging by grainy Paparazzi photographs from their holiday together.
In photos obtained by Page Six, the rumoured couple were seen kissing, cuddling, sunbathing, sipping wine and reading on a boat together in Tuscany. Jealous? Us? Yes.
The pair fitted in perfectly with the chic aesthetic of their Italian trip with Wilde wearing a high-waisted navy bikini while the former One Direction band member wore an open navy shirt, cap and black swim trunks.
21/06/21: Olivia Wilde expertly dodges Harry Styles questions from Paparazzi
After what was reportedly a long, 10 hour flight from London, instead of grabbing a takeaway, watching TV and catching up on sleep, Olivia Wilde arrived back in Los Angeles this week and was greeted with a barrage of questions from awaiting Paparazzi.
In a video shared on E! News, the aforementioned Paparazzo had many questions for Wilde, but particularly about her rumoured boyfriend, Styles. Questions like, 'does Harry Styles - who Wilde met while directing on her upcoming film Don't Worry Darling - have an Oscar in his future' were met with a stoic face from Wilde who remained polite, telling the cameraman: 'You know I'm not gonna talk. You know it's not gonna happen.'
The only moment Wilde let up slightly was when the persistent Paparazzo said: 'I think he's really good, he's got a lot of potential right?' to which Wilde smiled and gave a slight nod.
Wilde was believed to have spent time with Styles in London over the past few months. According to reports, she was also there with her children as her ex-partner Jason Sudeikis had been filming the second season of his Golden Globe-winning football comedy Ted Lasso.
15/03/21: Olivia Wilde shared a subtle post after Harry Styles won a Grammy
Harry Styles won his first ever Grammy award on March 14, 2021 when he was awarded the Best Pop Solo Performance Grammy for his hit song 'Watermelon Sugar'.
Styles pretty much dominated the internet the next day (along with Beyoncé and Megan Thee Stallion, of course) with celebrations of his win, his two-piece Gucci leather suit, minus-shirt, but plus feather boa situation which he wore to perform, the very cordial exchange he had with fellow Grammy winner and ex-girlfriend Taylor Swift, who also gave him a standing ovation when he won the award.
However, among the mass hysteria celebrating Styles there was another reaction which might have gone unnoticed.
On Monday, Wilde shared a photo of Beatles legend Sir Paul McCartney biting into a watermelon along with a *raised hands* celebratory emoji.
We see what you did there, Olivia Wilde.
What have Olivia Wilde and Harry Styles said about each other?
After wrapping on her second directorial movie, Don't Worry Darling, which was released on September 23, 2022, Wilde paid tribute to her cast and crew for working so tirelessly on her film, during a pandemic.
Among the tributes the House alum shared (including a post devoted to lead actress Florence Pugh) was one dedicated to Styles. Naturally, the post did not suggest or hint that the colleagues were anything more than friends, Wilde was simply paying tribute to the former One Direction singer as an actor and person.
Sharing a picture of Styles sat in a suit on an old school American car (the film is set in the 1950s), Wilde begun by praising the 'Adore You' singer for 'relishing' the chance to play a supporting role in a female-led film which she said is a rare feat for a male actor in Hollywood.
'Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold centre stage as our “Alice”, but he infused every scene with a nuanced sense of humanity,' Wilde wrote.
Writing of Styles' 'humility and grace' while working on the project, the director also paid tribute to the star's talent, saying he 'blew us away every day with his talent, warmth, and ability to drive backwards.'
Wilde and Styles were then pictured in a group shot of the cast and crew taken by actor Asif Ali, as the project wrapped.
When did rumours start swirling that Harry Styles was dating Olivia Wilde?
On Monday January 4, 2021, the New York Post's celebrity gossip column Page Six shared photos of Styles attending his agent's wedding in Montecito, California - wearing a dressing gown in some pictures.
In additional photos, the Styles (wearing suit trousers, a blouse-style shirt and a velvet tie) was seen holding hands with Wilde - also dressed in a floral wedding guest-appropriate dress while both wearing face masks - as they walked towards the ceremony.
According to Page Six, the photos were evidence that the two were officially dating, and reports suggested the couple 'took their romance public' by attending the wedding together and holding hands while doing so.
Following the wedding guest photos, more pictures were published by the Mail Online showing Wilde and Styles arriving back at the 'Adore You' singer's home in Los Angeles after the wedding.
Neither Styles nor Wilde addressed the rumours or reports but, of course, the internet had thoughts:
Are Harry Styles and Olivia Wilde single?
Other than Wilde, Styles has not been linked to anyone in the public eye since his relationship with the model Camille Rowe, which ended in 2018. Prior to that, Styles famously dated both Kendall Jenner and Taylor Swift.
In 2020, it was reported that Wilde had ended her long-term relationship with Jason Sudeikis, with whom she shares two children. According to sources, the couple ended on good terms, remaining close and are committed to co-parenting together, with photos of the two hugging and talking in December suggesting just this. In fact, shortly after the pictures of Styles and Wilde did the rounds, the Booksmart director was photographed chatting to Sudeikis.
Did they work on a film together?
Yes, they did. So when rumours first started swirling about their romance, we knew it was a possibility that Wilde and Styles could just be friends. This was due to them having got to know each other very well on the set of Wilde's Booksmart directorial follow up, Don't Worry Darling, which wrapped in February 2022.
Friends can hold hands too. And, in fact, this is what a lot of Styles' fans suggested on Twitter at the time:
Wilde cast the British singer - who previously starred in Christopher Nolan's film Dunkirk - opposite Florence Pugh in the psychological thriller about a married couple set in 1950s suburbia (Gemma Chan, Kiki Layne and Chris Pine also star). Speaking to Vogue when Styles covered the issue in 2022, Wilde gave her thoughts on why she picked the singer (who reportedly replaced original choice, Shia La Boeuf).
She noted:
'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. And 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.'
Whatever the situation appeared to be between the stars, we couldn't wait to watch Don't Worry Darling, and as Styles recently said (with the help of Phoebe Waller-Bridge), it's important to 'treat people with kindness'.
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