Harry Styles Responds To Question About Falling 'In Love' With Olivia Wilde On 'Don't Worry Darling' Set

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Harry Styles And Olivia Wilde Have Reportedly Taken The Next Step In Their Relationship
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Photo credit: Cindy Ord - Getty Images
Photo credit: Cindy Ord - Getty Images

Harry Styles has had quite a busy year, what with a concert tour and the launch of his new beauty brand Pleasing, but fans continue to be fascinated by his rumoured romance with Olivia Wilde.

Last year's Hollywood news kicked off with reports that boyband star turned critically acclaimed artist and international mortal of affection Harry Styles and respected feminist and all-round cool girl actress/director Olivia Wilde are dating.

The rumour mill went into overdrive in January when the pair were spotted together... and not just on the set of the upcoming movie they're working on.

Here's what we know:

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 a new 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.

Photo credit: Neil Mockford - Getty Images
Photo credit: Neil Mockford - Getty Images

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 a new interview, the Coachella 2022 headliner has said that 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.

Photo credit: Kevin Mazur - Getty Images
Photo credit: Kevin Mazur - Getty Images

‘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]'

Photo credit: Instagram
Photo credit: Instagram

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 has 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 has 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 a recent 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 rumoured relationship appear to be going from strength to strength, judging by grainy Paparazzi photographs from their recent 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 is 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 has been filming the second season of his Golden Globe-winning football comedy Ted Lasso.

Poor Olivia Wilde, let's leave her to put her feet up shall we.

15/03/21: Olivia Wilde shared a subtle post after Harry Styles won a Grammy

Harry Styles won his first ever Grammy award on Sunday evening (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.

Photo credit: Kevin Winter - Getty Images
Photo credit: Kevin Winter - Getty Images

However, among the mass hysteria celebrating Styles there was another reaction which might have gone unnoticed.

On Monday, Wilde - rumoured to be dating Styles (you can read all the evidence below, though they have not confirmed or denied rumours) - shared a photo of Beatles legend Sir Paul McCartney biting into a watermelon along with a *raised hands* celebratory emoji.

Photo credit: Olivia Wilde - Instagram
Photo credit: Olivia Wilde - Instagram

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 you can read more about below), 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 (included 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.

Why do people think Harry Style is dating Olivia Wilde?

On Monday January 4, 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, but we'll let that slide for now.

In additional photos, the 26-year-old (wearing suit trousers, a blouse-style shirt and a velvet tie) is seen holding hands with Wilde - also dressed in a floral wedding guest-appropriate dress while both wearing face masks - as they walk towards the ceremony.

According to Page Six, the photos are evidence that the two are officially dating, reporting that 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 have addressed the rumours or reports but, of course, the internet had thoughts:

Are Harry Styles and Olivia Wilde single?

Yes. 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.

At the end of last year, 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.

Photo credit: Kevin Mazur - Getty Images
Photo credit: Kevin Mazur - Getty Images

But aren't they just working on a new film together?

Yes, they are, as we've mention above. So it is also a possibility that Wilde and Styles are just friends having recently 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.

Friends can hold hands too. And, in fact, this is what a lot of Styles' fans have suggested on Twitter:

Wilde cast the British singer - who previously starred in Christopher Nolan's film Dunkirk - opposite Florence Pugh in the upcoming 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 last year, 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 between the stars, we can'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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