Olivia Wilde and Harry Styles Breakup: Look Back at Their Relationship

You know it's not the same as it was.

Harry Styles and Olivia Wilde were together for nearly two years before calling it quits in November 2022.

The news comes months after the controversy surrounding their movie Don't Worry Darling—and after they'd each spoken out somewhat publicly about their relationship.

Just before the release of Styles' album Harry's House in May 2022, Howard Stern asked Styles in an interview, "You fell in love on a movie set?"

Styles, a bit flustered, replied, "Oh, wow, how to answer this question ... 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. 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."

Stern also asked the singer about his racy song "Cinema," which the King of All Media assumed was about Wilde.

"When I write songs, they kind of start out just, I guess, mine," the one-time One Direction heartthrob said. "I think it's important to write from what you're going through at the time and trying to turn life into what you make. I guess it's like, the most you can kind of capture a moment is kind of being true to that."

For her part, Wilde told Vogue in January 2022, "It’s obviously really tempting to correct a false narrative, but I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you. All that matters to you is what’s real, and what you love, and who you love. In the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us. I’m happier than I’ve ever been. And I’m healthier than I’ve ever been, and it’s just wonderful to feel that."

We suppose it was good while it lasted!

Related: The Drummer and the Hambone! Get to Know Olivia Wilde and Jason Sudeikis’ Kids, Otis and Daisy

Are Harry Styles and Olivia Wilde dating?

In early January 2021, a source told PEOPLE that the 36-year-old Wilde and 26-year-old Styles had already been dating “for a few weeks.” Wilde and Styles reportedly were getting serious as of December 2021. Since then, they've been photographed together quite a bit all around the world. However, as of November 2022, the pair were reportedly "taking a break" from the relationship.

How did Harry Styles and Olivia Wilde meet?

She was actually his director on the set of the upcoming feature film Don’t Worry Darling, which costars Oscar nominee Florence Pugh and will mark one of Styles’ most significant acting roles to date. Styles’ role as Pugh’s husband had originally been filled by Shia LaBeouf, but Wilde fired him from the production because he violated what she has called her “no a**hole” rule.

In a sitdown between Wilde and fellow female director Emerald Fennell, who helmed this year's critically-acclaimed Promising Young Woman, Wilde explained that the rule “puts everybody on the same level” on set.

Wilde also spoke to Vogue back in December 2020 about landing Styles to replace LaBeouf. “I did a little victory dance when we heard that we officially had Harry in the film…I’m really grateful that he is so enthusiastic about that element of the process—some actors just don’t care.” She added, “To me, he’s very modern,” said Wilde of Styles, “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.”

In August 2022, she told Rolling Stone of her choice to hire Styles for Don't Worry Darling, “We were looking for someone with innate warmth and palpable charm. The entire story depended on the audience believing in Jack.”

Related: Find Out Olivia Wilde's Net Worth

Are Harry Styles and Olivia Wilde engaged?

That's a hard no. Back in late January 2021, a tabloid magazine claimed that the brand-new couple was "already planning to say 'I do,'" but there's been no proof of that. Wilde has never been seen wearing an engagement ring during their relationship.

That said, even if they were, we doubt they'd reveal it to the world—they never even stood next to each other during the Don't Worry Darling press tour!

What do Olivia Wilde and Harry Styles think of his fans?

A small but very vocal section of Styles' fandom spends a lot of time hating Wilde. "That obviously doesn’t make me feel good," Styles told Rolling Stone in August 2022, adding, "Can you imagine going on a second date with someone and being like, ‘OK, there’s this corner of the thing, and they’re going to say this, and it’s going to be really crazy, and they’re going to be really mean, and it’s not real.… But anyway, what do you want to eat?’ "

"It’s obviously a difficult feeling to feel like being close to me means you’re at the ransom of a corner of Twitter or something," he continued. "I just wanted to sing. I didn’t want to get into it if I was going to hurt people like that."

Wilde, for her part, described Styles' fans to Rolling Stone as "deeply loving people," adding diplomatically, “What I don’t understand about the cruelty you’re referencing is that that kind of toxic negativity is the antithesis of Harry, and everything he puts out there. I don’t personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness.”

Related: Harry Styles' Net Worth From One Direction and Solo Success

Why did Olivia Wilde and Harry Styles split?

Friends of the couple explained that there were a few factors leading to the November 2022 breakup.

"He's still touring and is now going abroad. She is focusing on her kids and her work in L.A.," a source told PEOPLE, adding, "It's a very amicable decision. They're still very close friends."

A friend of the couple explained, "Right now, they have different priorities that are keeping them apart." The pal added, "The public pressure on them has been difficult. They've had ups and downs throughout the relationship."

When did Olivia Wilde and Jason Sudeikis break up?

News of their split (after a lengthy nine years together) broke in November 2020, but it was reported at the time that they'd actually called it quits on their relationship months prior and had managed to keep the news on the down-low. "It's been amicable and they’ve transitioned into a great co-parenting routine," an insider told PEOPLE. "The children are the priority and the heart of the family’s relationship." The exes share 6-year-old son Otis Alexander and 4-year-old daughter Daisy Josephine.

Wilde made it clear while promoting Don't Worry Darling, however, that she didn't cheat on Sudeikis with Styles.

"The complete horses—t idea that I left Jason for Harry is completely inaccurate," she told Vanity Fair in an interview published Thursday, Sept. 8, 2022. "Our relationship was over long before I met Harry."

"Like any relationship that ends, it doesn't end overnight," she continued. "Unfortunately, Jason and I had a very bumpy road and we dissolved the relationship towards the beginning of the pandemic. We were raising two kids during lockdown, so we co-parented through that time. Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to not, because we could be better parents as friends who live in different houses."

"I don't understand the need to create false narratives around this kind of stuff," she said. "It's like, haven't the kids been through enough?"

Related: Did Olivia Wilde Really Fire Shia LaBeouf From Don't Worry Darling?

Why didn't Olivia Wilde and Jason Sudeikis ever get married?

"Bottom line: they had issues and they were never going to get married," a source alleged to Us Weekly about the longtime couple never actually making it down the aisle after getting engaged in January 2013, about two years after they started dating. "Of course, there were arguments and fights over career decisions and where to live. Like most couples, they had disagreements, they were bicoastal but Jason loved living in New York and Olivia, who was born in NYC, was leaning more toward Los Angeles." Neither Wilde nor Sudeikis has confirmed or denied this, however.

Related: Harry Styles Speaks Out On 'Spitgate'

Who else has Harry Styles dated?

Uh, you may have heard about his fling with a certain world-famous pop star named Taylor Swift. The two dated briefly from October 2012 to January 2013, when he was at the height of his 1D fame. Their rough breakup famously occurred during an excursion to the British Virgin Isles, which resulted in the famous "sad Taylor Swift on a boat" photo.

"Certain things don't work out," Styles said in a 2017 interview withRolling Stone. "There’s a lot of things that can be right, and it's still wrong." Rumor has it that Swift got her revenge by going on to write two of her best breakup songs about Styles, including "Out of the Woods" and "Style." (Subtle!) Some say there was an Easter egg for him on her latest album evermore.

Styles later on-off dated model Kendall Jenner, but the two had a much more amicable split.

He even interviewed her once while guest-hosting The Late Late Show With James Corden, where he convinced her to play a hilarious (and somewhat revealing) game of "Spill Yer Guts or Fill Yer Guts."

Jenner's not the only model in Styles' dating history; he's also been linked to such Victoria's Secret angels as Nadine Leopold, Sara Sampaio, Georgia Fowler and Camille Rowe.

Next, learn all about Florence Pugh's love life.