Olivia Wilde and Harry Styles: A Look at Their Tumultuous Relationship

olivia wilde and harry styles with a broken heart between their pictures
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Olivia Wilde and Harry Styles are two big names in the entertainment industry – she’s an iconic actress, and he’s one of the most famous singers and actors today. However, there’s a reason why people associate their names together. For several months, they were an item, but there was quite a bit of drama surrounding their time together.  

If you want to learn more about the relationship between Olivia Wilde and Harry Styles, you’re in the right place. Find a place to sit down as we dive into the dating experience of two iconic individuals, from how their relationship started to their extreme controversies in the movie Don’t Worry Darling.

How Did Their Relationship Start?

Although the rumors of their relationship didn’t emerge until much later, Olivia Wilde and Harry Styles’ relationship began around the beginning of the filming of Don’t Worry Darling. There were reportedly many long days on set, which allowed time for their relationship to flourish and grow into something stronger. From there, their love took off.

The first indication that something was at play was Olivia Wilde’s split from her husband, Jason Sudeikis, on November 13th, 2020. After seven years of marriage and two children together, they decided to part ways and began to co-parent their children.

On January 4th, 2021, Harry and Olivia were pictured holding hands at the wedding of Harry Styles’s agent. He gave a speech at the wedding and, according to some sources, Harry Styles referred to Olivia Wilde as his girlfriend as he spoke.

Related: Are You a Harry Styles Fan?

olivia wilde arriving at an event
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What is Their Age Difference?

One of the controversies in the Olivia Wilde and Harry Styles relationship was the age difference. There was a ten-year age gap between the two, with Olivia Wilde being 36 while Harry Styles was 26 when they met and began dating. While the duo seemed fine with the gap, many assumed there would be future issues with this difference. 

There were many rumors surrounding the duo’s age gap, and Olivia Wilde reported that it was hard to resist the urge to correct false narratives she’d heard about her love life. While dating, she revealed that they were happy and enjoyed their life together.

How Long Did Olivia Wilde and Harry Styles Date?

To correctly estimate the lifespan of Olivia Wilde and Harry Styles’s relationship, we need to start at the beginning. Let’s review the timeline of the duo’s time together.

As discussed, Olivia Wilde and Harry Styles were first pictured together at a wedding. The next hint at their relationship happened on February 15th, 2021, when Wilde applauded Harry’s acting ability for her movie on her Instagram account. 

When June 2021 rolled around, it was common to see photos of the pair holding hands in public. In October of 2021, Olivia mentioned living in London. The couple had become very serious at that point.

In April 2022, Olivia Wilde attended Harry Styles’s performance at Coachella. Fans took a video of her cheering him on, and they later were spotted together enjoying other performances at the festival. 

In May 2022, Harry Styles’s new album dropped. There were references to his relationship here, such as the lyrics “Leave America, two kids follow her.”

The following months involved much drama, including Wilde being served custody papers onstage from her ex at a public forum. She and Styles revealed that they wanted to keep their relationship as private as possible. 

One of the last times the duo were seen publicly enjoying their time together was at a September 2022 concert. Wilde cheered for Styles from the audience, dancing during some of his most popular song selections. 

harry styles on stage playing guitar
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Why Did Olivia Wilde and Harry Styles Break Up?

There are disputing sources on why Olivia Wilde and Harry Styles broke up. The most public opinion is that they were under a lot of pressure from the public status of their relationship and had several serious issues that they ended up being unable to work through. Although Wilde wanted to continue forward, Styles seemed less excited.

Since their initial break, there have been extensive rumors about the breakup, most centering around their time on the set of Don’t Worry Darling. However, they’ve denied many of these rumors and stated they were still close friends.

Did Harry Styles Get Back With Olivia Wilde?

Although there were many rumors about the duo getting back together, they never reconciled after their split. In fact, some sources claim that Harry Styles felt like he dodged a bullet by breaking up with Olivia Wilde and had no desire to get back together with her. Some sources claim Olivia Wilde wanted to get back together with him, but this was never proven.

One source claimed to see Olivia Wilde in one of his old t-shirts several months after the breakup. Although they stated the split was amicable, it seems Harry Styles was more in favor of the breakup than the actress, writer, and director.

Who Was Olivia Wilde’s Husband?

Olivia Wilde has had several relationships throughout her life. The relationship right before Harry Styles was with Jason Sudeikis, whom she was with for seven years and had two children with. Although they seemed to have a serious relationship, they never got married. However, they were engaged for a short period. 

Olivia Wilde did have a husband before Jason Sudeikis – Thai-Italian filmmaker and photographer Tao Ruspoli. They met through a friend of the family and were married from 2003-2011. They eloped but ended up breaking up in 2011, with Wilde reportedly feeling like she’d rushed into the relationship. 

Related: 51 Best British Singers

olivia wilde and jason sudeikis arriving at an event
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The Don’t Worry Darling Controversies

One of the biggest issues with the Wilde and Styles relationship was where they met – the set of Don’t Worry Darling. These rumors went on to hurt their relationship. 

A big rumor was the distractions Styles and Wilde caused on set. There were ample tensions, especially as the relationship began before Wilde and Sudeikis resolved all their issues.

There was also a strange rumor that Harry Styles spit on Chris Pine at the movie’s premiere, which cast a strange light on cast tensions. Wilde was forced to defend him publicly. 

There are many critics who blame the fall of the Harry Styles and Olivia Wilde relationship on the movie related controversies, but as far as we know, their relationship didn’t work because they are just two very different people.

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Written by Hope Davis

Long-time music lover Hope became a full-time writer in 2020 after being laid off from her regular job due to COVID-19. She now spends her time traveling the world to see her favorite bands while writing about them!


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