A Brief History of Harry Styles and Olivia Wilde

Allison Lillestol and Lianna Enright, Copy- Editor

Harry Styles and Olivia Wilde. Holivia. Olivrry.

You have probably heard these two names all over Tik Tok ever since the infamous Venice Film Festival. This couple’s extensive, and dare I say confusing, relationship has a long history. But don’t worry—we’re here to break it down for you.

September 2020:

This is the month where it all began. Harry Styles fans all over the world gathered by the nearest phone to see the announcement of the new film “Don’t Worry Darling” with Harry Styles as a lead and Olivia Wilde as a director with a role in the film.

October 2020:

This is the month when the filming of “Don’t Worry Darling” began, and thus began a plethora of behind the

The iconic couple looking fantastic! (Photo taken from Google Images via Creative Commons License)

scenes photos of Harry Styles on set. But Harry Styles wasn’t the only one breaking the internet at the time, which leads us into the events of November.

November 2020:

Olivia Wilde, actress and filmmaker, announced the end of her seven-year-long engagement to Jason Sudeikis, strengthening the relationship rumors about her and Harry Styles while also creating new speculations. Many fans thought nothing of it until the events of January.

January 2021:

At the start of the year, photos came out of Wilde and Styles holding hands at a friend’s wedding. This was one way to start the New Year off with a bang. But buckle in, this is only the beginning of the drama between the two of them.

April 2021: 

A few months later, Styles and Wilde were spotted together in London. During this time, there were rumors of their engagement floating around, which neither of them addressed. The rumors disappeared a few weeks later, and nothing has been said about it since.

July 2021: 

The couple was spotted together on vacation on the coast of Italy. They were having the time of their lives on a boat while their large fan base was going crazy over their relationship—classic Harry Styles.

September 2021:

Harry Styles’ tour, Love on Tour, began! Olivia Wilde was seen in the audience at almost every show. I think we all wish we were Olivia Wilde during this time.

March 2022: 

After disappearing for a while, Styles and Wilde were seen together holding hands while taking a stroll in London. This seems like just another spotting to any normal person; however, this interaction was a huge deal for fans, as it was the first time in 7 months the couple had been seen together. To say the fans were shocked would be an immense understatement.

Florence Pugh and Harry Styles looking fabulous in the trailer of “Don’t Worry Darling.” (Photo taken from Google Images via Creative Commons License)

April 2022:

After Styles’ several performances at Coachella that brought him even more fame, he was spotted with Wilde in the crowd watching Billie Eilish perform. Honestly, it was a little weird watching Harry Styles attend a concert rather than be the performer. But I’m not one to complain about videos of him jumping up and down to Billie Eilish, so why not let the man enjoy quality time with his girlfriend?

May 2022: 

Everything seemed to be going smoothly in their relationship until May. Styles and Wilde were spotted on yet another vacation in Italy. Seems normal right? Wrong. Styles’ dedicated fan base was quick to pick up on the fact that he and Olivia Wilde seemed to be quite distant on this vacation compared to their last one. Not only were they walking far apart the entire time, but I don’t think they were seen making physical contact once on the whole trip. This didn’t sit well for the Harries.

However, later that month the couple was seen at an airport in New Jersey. A few days later, they were spotted back in London having dinner together. At this point, the speculations about their relationship problems had died down and everything seemed normal again.

June 2022:

In June, Styles and Wilde were seen swimming at a beach in Dublin. During their beach trip, the couple was extra affectionate. They walked along the beach with their arms wrapped behind each other’s backs, leaning together as they walked. Styles even stopped to give her a kiss on the cheek.

Harry Styles wearing a full, custom-made Gucci suit. (Photo taken from Google Images via Creative Commons License)

August 2022:

Styles and Wilde were seen walking in Manhattan, New York before one of his many shows in Madison Square Garden. The same day, they were seen leaving a restaurant while holding hands.

Everything seems to be going smoothly until suddenly drama erupts once more.

September 2022:

The Venice Film Festival. What didn’t happen at the Venice Film Festival?

In only a few days, Harry Styles and Olivia Wilde managed to sit as far away from each other as they could, Florence Pugh made a dramatic entrance, and Harry Styles spit on Chris Pine (allegedly). They all did this while wearing designer brands. I guess they might as well look good while stirring up all this drama.

Fans began speculating about a break-up between the couple because of their distance during the festival. But what really shocked the internet? You guessed it, the “Miss Flo” video.

A video made by Olivia Wilde that was sent to Shia LaBeouf, came out exposing her feelings on the movie’s cast change. In the video, we find out that Shia LaBeouf was originally supposed to play Harry Styles’ role in the movie. Although the true reason why he left the movie is uncertain, this video makes it very clear that she wanted him to stay.

But the most notable moment in the video was when Olivia Wilde reffered to Florence Pugh as “Miss Flo,” and said how this might be a wake-up call for her. This may have been in reference to the tension between LaBeouf and Pugh. Naturally, the internet did not appreciate Wilde’s nickname.

What also caught fans’ attention was the press conference that Florence Pugh did not attend due to her scheduling conflicts with another movie.

The infamous movie poster for “Don’t Worry Darling.” (Photo Taken from Google Images)

During the conference, Wilde had very little to say about the drama and did not want to add any comments. But at this point, it should be no shocker that more drama followed.

Pugh made a grand entrance onto the festival’s red carpet wearing a black Valentino dress. Fans on Twitter noticed she stayed very far from Wilde during the photos and greeted all of her fellow co-stars except for Harry Styles and Olivia Wilde.

During the premiere, a video of Harry Styles sitting down next to Chris Pine became one of the biggest moments of the night. Fans were convinced that Harry Styles, our beloved British icon, spit on Chris Pine.

Harry Styles and Chris Pine’s press teams both spoke out denying the rumors. But if you ask me, it was a very convincing video.

Overall, the past two years have been a whirlwind for this couple. I think it’s fair to say, “Don’t Worry Darling ” has become very worrying.