An Official Timeline of Harry Styles and Olivia Wilde’s (Kinda Drama-Filled?) Relationship

Starr Bowenbank
·7-min read
Photo credit: Getty Images
Photo credit: Getty Images

From Cosmopolitan

Sorry to break it to you hopefuls, but Harry Styles is now off the dating market. In case you somehow have not heard, Harry is currently dating Olivia Wilde—you know, who casually happens to the director of Harry’s upcoming film project Don’t Worry Darling. Although Harry and Olivia have been an item for, oh…five minutes, there are TONS of questions about their quickly evolving romance, like: Exactly when did Harry and Olivia start dating? and Was Harry part of Olivia and her ex-fiancé Jason Sudeikis’s breakup?? The answers to your burning questions await you below, my nosy friend.

Photo credit: Getty Images
Photo credit: Getty Images

Early 2020

Olivia and her fiancé Jason Sudeikis split after seven years together. The news won't break for a few more months, but when it does, sources report the breakup is "amicable." Keep this in mind as everything else unfolds. 👀

September 11, 2020

Deadline reports that Harry is cast in Olivia’s newest project, Don’t Worry Darling, opposite Midsommar’s Florence Pugh. Olivia serves as the director of the project and replaces Shia LeBeouf with Harry after a falling out. Harry fans everywhere rejoice!

November 13, 2020

Sounds like Olivia is juuust as excited as the fans about Harry's casting news. In Harry’s cover interview with Vogue, Olivia reveals that she and the film’s costume designer, Arianne Phillips, are extra happy to have Harry around because of his love for fashion.

“She [Arianne] and 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,” Olivia says. “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.”

But Olivia doesn’t stop there—she adds, “To me, he’s very modern, and I hope that this brand of confidence as a male that Harry has—truly devoid of any traces of toxic masculinity—is indicative of his generation and therefore the future of the world. I think he is in many ways championing that, spearheading that. It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.” Iiiiinteresting.

Also on November 13, 2020

Just a few short hours after Olivia praises Harry in print for being an amazing, talented, and fashionable human being, the breaking breakup news hits: Olivia and her fiancé Jason Sudeikis ended their engagement after seven years.

A source tells People “the split happened at the beginning of the year,” with the good news being that their breakup has “been amicable and they’ve transitioned into a great co-parenting routine. The children [son Otis Alexander, 6, and daughter Daisy Josephine, 4] are the priority and the heart of the family’s relationship.”

Photo credit: John Shearer - Getty Images
Photo credit: John Shearer - Getty Images

An Entertainment Tonight source backs up Olivia and Jason’s “amicable” split and claims “they just fell out of love in a romantic way but still have love toward one another as people.” Thankfully, Olivia and Jason “consider themselves friends and co-parents first and foremost.”

A separate ET source made a point to add “there was absolutely no drama or scandal, they just didn’t work as a couple anymore. If you’re looking for a juicy story, there just isn’t one.” File that for later.

January 4, 2021

Harry and Olivia are seen holding hands at a wedding—aka one of the most couple-y events you can possibly attend with a significant other—and all hell breaks loose on the internet. Naturally.

“They were in Montecito, California, this weekend for a wedding,” a source tells People. “They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks.” 😱

Entertainment Tonight also has a bunch of intel on Harry and Olivia’s romance and a source basically says they developed a deeper connection while on-set. “Olivia and Harry are together for long days on-set and have gotten to know each other really well, so it’s all very organic.” Olivia’s treading carefully with her and Harry’s relationship because she “wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully.”

And in case you’re wondering about Jason’s feelings about this, ET’s source reminds everyone that he and Olivia actually split over a year ago, “so it’s not like she’s rushing into something.…Olivia and Jason talk all the time and are still close because of the kids. It’s highly unlikely he was blindsided by this news.” Again—file that for later!!!

January 8, 2021

Apparently, there might be more to Olivia and Harry’s relationship than meets the eye—and it’s stirring up some drama. Well, according to a Page Six source, at least.

“People have tried to make out that Harry and Olivia have only been dating for the past few weeks, but that’s not right,” the source says. “Jason found out about Harry and pushed the conversation. Olivia then asked for a separation and news of the split was made public.”

Everyone right about now:

January 9, 2021

Despite those wedding pics leaking to the internet, Olivia and Harry swear they “were able to keep their relationship under wraps for a bit before it became public knowledge,” a source tells Us Weekly. “They were very careful about it and even sleuth-y at times, although the small group of people who were on-set with them every day eventually figured it out.”

Oh! And to make things abundantly clear, the source adds, “Harry did not break up an engagement.” Good to know.

Remember how that ET source said there was “no drama or scandal” in Jason and Olivia’s split and that it was “highly unlikely” Jason could feel blindsided by the news? Welp, People reports Jason “is absolutely heartbroken about the split.”

“There is still a lot of love there, and he would like to have hope that maybe there’s a way for them to repair things,” says the source. “But what happens next remains to be seen.”

January 10, 2021

The people—i.e., Harry fans—want to know: Did Mr. Styles factor into Olivia and Jason’s split? An Us Weekly source seems to think so, even though Olivia and Jason split long before Harry was cast in her movie.

“Olivia called off the engagement in early November but only after she already had gotten close to Harry,” the insider claims, disputing the breakup timeline. “Whether Harry knows it or not, he was a reason for the split and it blindsided Jason—he totally adores Olivia and is devastated. Family is his biggest priority.”

A second source immediately jumps in with a counter story, saying that “the engagement was called off early last year, as was previously reported. Harry was in no way the reason for their split.”

January 13, 2021

Truly would love to know who has all the intel about Jason’s feelings throughout *gestures hands* all of this, but an all-knowing source returns with another sad nugget from his side of the breakup.

“Jason’s had no option but to step back and let Olivia do her thing, but he [has his fingers crossed] that this is just a phase and that Olivia will snap out of it or that Harry will get bored and move on before too long,” a source tells Us Weekly. And if that wasn’t already…a lot, Jason is apparently “desperate” to win Olivia back so they can “repair their family.” Will Jason and Olivia ever get back together? We! Shall! See!!!

Aaand there ya have it, folks—stay tuned for any and all future developments about 2021’s hottest new couple!

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