Timeline of Harry Styles and Olivia Wilde’s relationship


Since reaching the heights of fame with One Direction, Harry Styles has carved out a unique solo career in music, winning a Grammy for his single “Watermelon sugar‘; acting, including his new role in my policeman alongside Emma Corrin; and fashion, like one of the stylish men, ever.

Naturally, when rumors began to circulate about his relationship with actress and director Olivia Wilde, some fans (perhaps the same ones who brought “I want to marry Harry” signs to One Direction concerts) were devastated. But there’s no need to get excited: Olivia is a multi-talented (and award-winning) woman, with roles in CO and disney Tron legacy, as well as directing the critically acclaimed film Booksmart. You have to admit that they are an incredibly cool couple.

Harry Styles is one of the best dressed men on the planet – just watch him win the British ‘Best Bachelor’ award

The couple confirmed their romance earlier this year (2021), after they were spotted holding hands at a friend’s wedding. Since then, we’ve been so invested in growing their relationship, from praising each other on social media, to frolicking on a yacht together. Yes, they really are living their best life.

Case in point: They were recently seen wandering through LA looking * very * in sync. With their arms draped around each other, Harry and Olivia both wore a white t-shirt, cutout jeans, sunglasses, sneakers, and a long necklace – serving up a relaxed (and beloved) vibe.

Here’s everything we know about the timeline of Harry and Olivia’s relationship so far, since they met on the set of Don’t worry darling to distribute PDAs in LA:

September 2020: Harry Styles is in the cast of Olivia Wilde’s new film Don’t worry darling

Deadline reports Harry replaced Shia LaBeouf in one of the lead roles in Olivia’s film Don’t worry darling. This is the second film she has directed (after Booksmart), and took to Instagram to celebrate the casting of Harry and Florence Pugh in the lead roles in the film, saying, “Very proud to be working with these good people.”

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November 13, 2020: Olivia praises Harry in an interview

In an interview with Vogue, Olivia described her and costume designer Arianne Phillips’ reaction to Harry’s casting, saying (via People), “She and I did a little victory dance when we heard we officially had Harry in the movie, because we knew he has a real appreciation for fashion and style.

“And this film is incredibly stylistic. It’s very high and opulent, and I’m really grateful that [Harry] is so excited about this part of the process, some actors don’t care. “

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Olivia continued, “To me he’s very modern, and I hope that mark of confidence as a man that Harry has – truly devoid of any hint of toxic masculinity – is indicative of his generation and therefore of him. future of the world.

“I think he defends that in a lot of ways, is the spearhead of it. It’s quite powerful and quite extraordinary to see someone in their position redefine what it can mean to be a man with confidence. “

November 13, 2020: Reports reveal that Olivia Wilde and her fiance Jason Sudeikis have separated

People are reporting that Olivia Wilde and Jason Sudeikis ended their engagement after seven years together. A source told People: “The separation happened at the start of the year. It was amicable and they moved into a great co-parenting routine. Children are the priority and heart of the family relationship.

Olivia and Jason have two children together, Otis Alexander and Daisy Joséphine.

Entertainment Tonight confirmed the breakup, saying, “They fell in love in a romantic way, but they still love each other as people. They see each other as friends and co-parents first and foremost. ”

Another source added: “There was absolutely no drama or scandal, they just didn’t work out as a couple anymore. If you’re looking for a juicy story, there just isn’t any more.”

November 16, 2020: Olivia responds to Candace Owens after criticizing Harry’s sartorial skills

After Harry Styles wore a Gucci gown on the cover of Vogue, author Candace Owens tweeted: “There is no society that can survive without strong men. The East knows it. The West , the constant feminization of our men at the same time as Marxism is being taught to our children is no coincidence.
It is an outright attack.

“Bring back the manly men.”

Olivia’s response was right, tweeting: “You are pathetic.”

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January 4, 2021: Harry and Olivia are seen holding hands at a wedding

Page Six gets photos of Harry and Olivia holding hands at the wedding of his agent – Jeffrey Azoff. Around the same time, People report that the couple “were affectionate with their friends, held hands and looked very happy”, confirming that “they had been dating for a few weeks”.

From Taylor Swift to Kendall Jenner (twice) … An exhaustive guide for anyone Harry Styles dated as he spotted Olivia Wilde hand in hand

January 5, 2021: Harry reportedly called Olivia a girlfriend during wedding speech

A source tells Page Six that Harry introduced Olivia as his girlfriend, saying, “A source said,” This relationship between Harry and Olivia is very new. Olivia directed Harry in the movie to Palm Springs, and there were literally 10 people on set, as they were strictly following COVID rules.

“Harry had stayed at James Corden’s house near Palm Springs during the filming, so they were able to be alone and keep their relationship a secret.

“So everyone was really surprised – and quite delighted – when Harry brought Olivia on a date to the wedding and introduced her as his girlfriend.”

January 9, 2021: Source reports Harry and Olivia initially kept their relationship ‘a secret’

US Weekly reported that an insider revealed, “Olivia and Harry were able to keep their relationship a little secret before it became known to the public. They were very cautious about it and even detectives at times, although the small group of people together with them every day finally understood. “

January 22, 2021: Source reports that Harry and Olivia’s relationship is not a publicity stunt

According to Entertainment Tonight, a source reports that the photos of Olivia and Harry holding hands are not staged, suggesting their relationship is really the real deal, saying: “[The wedding photos were] absolutely not disclosed or staged for any sort of promotional reason. “

February 6, 2021: Harry and Olivia would be very happy together

Source tells People Harry and Olivia “seem very serious” and “spend all their time together” as they continue to shoot Don’t worry darling. The source added that Olivia is “very happy with Harry,” the source adds.

February 14, 2021: Olivia shares a sweet tribute to Harry on Instagram

Olivia posted a photo of Harry lying in a car with a very cute caption, praising him for playing a supporting role in a project led by women. She wrote:

“Little known fact: Most male actors don’t want to play supporting roles in movies directed by women. so hard to get funding for films with a focus on female stories. No kidding, it’s hard to find actors who understand why it might be worth allowing a woman to take center stage.

Enter: @harrystyles, our “Jack”. Not only did he relish the opportunity to let the brilliant @florencepugh take center stage as our “Alice”, but he infused every scene with a nuanced sense of humanity. 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, his warmth and his ability to back down. “

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February 2021: Olivia and Jason Sudeikis would be on better terms

Entertainment Tonight reports that, according to an insider, “Jason was initially very hurt about Harry and Olivia’s relationship, but now that he’s doing his own thing, things between him and Olivia have improved. They’re rebuilding their relationship again. friendship and co-parents together. “

March 16, 2021: Olivia posts not-so-subtle tribute to Harry on Instagram after his Grammy win

After Harry won his first Grammy for Best Pop Solo Performance for his single, “Watermelon Sugar” Wilde appeared to offer a subtle form of kudos for his Instagram stories. She posted a snap of Paul McCartney slipping into a watermelon, which is clearly a reference to Harry’s hit song, isn’t it?

June 4, 2021: Harry and Olivia are reported to be getting closer as a couple

According to ET Online, a source reported that Harry and Olivia had “had a great time” in London together. Adding that they “took a walk outside in the park and made no secret of their relationship” and that they “became even closer as a couple”.

The source continued, “Yesterday they enjoyed lunch outside and looked incredibly cute together. They were both in a good mood and left the restaurant holding hands. Harry put his arm up. around Olivia as they walked home. “

A second source added: “Harry and Olivia have been inseparable. Of course, that’s partly because they’re in a bubble for their movie, but even since it’s over, they still spend all of their time together. . “

July 5, 2021: Harry and Olivia are seen frolicking on a yacht

Page Six obtains pictures of Harry and Olivia kissing on a yacht in Italy. Jealous? We?

Keep the PDAs coming, folks!

For more on Glamor UK’s Lucy Morgan, follow her on Instagram @lucyalexxandra.


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