Everyone was pretty shook when news hit the web that Harry Styles was dating Olivia Wilde. Yep, for those who missed it, the One Direction member and the actress were spotted holding hands on January 4, 2021, at Styles’ manager, Jeff Azoff‘s wedding, and the internet quickly went into a frenzy over the new pairing.
“They were affectionate around their friends, held hands and looked very happy,” an onlooker told People Magazine at the time. “They have dated for a few weeks.”
Plus, get this — a source even revealed to Us Weekly that the singer referred to the star as his “girlfriend” during his speech at the wedding!
Although they seemed as happy as could be together, things got a little complicated when reports started to emerge that claimed Styles was the reason that Wilde ended her seven-year relationship with Jason Sudeikis, and that he was “beyond distraught” about the entire thing. So did Wilde’s feelings for the “Sign of the Times” crooner really cause her and her fiancé to end their engagement? And did their relationship start before or after her split from Sudeikis? Not to worry, you guys, because we went ahead and broke down their entire love triangle for you. Here’s what you need to know…
First Off, When And How Did Olivia Wilde And Harry Styles Meet?
The two stars first met in late 2020, after Styles was cast in Wilde’s upcoming movie, Don’t Worry Darling. And after Styles landed his role in the new flick, the 36-year-old, who is directing and starring in it, couldn’t stop gushing over him to Vogue Magazine.
“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,” she explained. “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. 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.”
It’s still unclear when Styles and Wilde officially started dating, but according to Entertainment Tonight, they grew super close during their time on set, and romantic feelings started to develop.
“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,” a source said. “[Wilde] wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully. So it’s not like she’s rushing into something.”
When Did Olivia Wilde And Jason Sudeikis Break Up?
In November 2020, People Magazine reported that Wilde and Sudeikis, who share two kids together — son Otis Alexander, 6, and daughter Daisy Josephine, 4 — and were gearing up to get married, had broken up. At the time, the outlet claimed that their split actually happened “at the beginning of the year” and that there was no bad blood between them.
“It’s been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship,” a source told them.
Plus, Entertainment Tonight also reported that there was “no drama” whatsoever surrounding their split.
“There was absolutely no drama or scandal, they just didn’t work as a couple anymore,” an insider dished. “If you’re looking for a juicy story, there just isn’t one. They adore each other and have nothing but the utmost respect for one another. They will continue to be each other’s biggest supporters, especially when it comes to parenting their children and their careers. They see each other all the time still.”
A second source added, “They just fell out of love in a romantic way, but still have love towards one another as people. They consider themselves friends and co-parents first and foremost. They are committed to co-parenting successfully for the sake of Otis and Daisy and have done a great job so far at staying connected in a healthy way for their relationship and for their children.”
But when Styles and Wilde were caught holding hands in January 2021, the story quickly changed. New reports emerged that claimed that Wilde actually started dating Styles in October, and that she and Sudeikis didn’t split until one month later — in November — and that he was not happy about the new relationship.
“Olivia and Jason were having issues, like any other couple, but Jason loves Olivia — he completely adores her, and that’s what makes this so sad. He’s always been committed to making their family work,” a source told Page Six. “People have tried to make out that Harry and Olivia have only been dating for the past few weeks, but that’s not right. Jason found out about Harry and pushed the conversation. Olivia then asked for a separation and news of the split was made public. Harry Styles is basically the reason for Olivia and Jason’s split.
ET also reported that Sudeikis was “in absolute shock” over the whole thing.
“Jason is beyond distraught. Of course Jason still has feelings for [Wilde]. This is a fresh split,” an insider explained. “He’s in absolute shock. He would like to repair things with Olivia and have his family back together.”
Another source told Us Weekly, “Olivia called off the engagement in early November but only after she already had gotten close to Harry. 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.”
However, days later, conflicting reports started to emerge. In a different article, Us claimed that this wasn’t the case after all, and that Wilde and Sudeikis were “already done” before she started her relationship with Styles.
“Harry did not break up an engagement,” another source insisted. Confusing, we know.
One final friend of the pair claimed, “Olivia and Jason talk all the time and are still close because of the kids. It’s highly unlikely he was blind-sided by this news. Olivia and Harry got close through working together on Don’t Worry Darling. Since her split from Jason, she has been more open to seeing new people. She’s always liked Harry and it was one of the reasons she cast him and, since then, she’s developed a thing for him.”
What Else Do We Know About Harry Styles And Olivia Wilde’s Relationship?
According to Us, Styles and Wilde were “very careful” to keep their relationship private at first.
“Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge,” an insider explained. “They were very careful about it and even sleuthy at times, although the small group of people who were on set with them every day eventually figured it out.”
Page Six also reported that talk show host James Corden helped them cover up their tracks!
“Harry had been staying at James Corden’s house near Palm Springs during filming, and so they were able to be alone and keep their relationship very secret,” they explained. “So everyone was really surprised — and rather delighted — when Harry brought Olivia as his date to the wedding, and introduced her as his girlfriend.”
The Sun added that their 10-year age gap definitely wasn’t a problem for them.
“They clicked immediately — they’re both very artistic, passionate people and it was one of those things where straight away everyone could see they had a spark,” a source said. “Clearly they’re enjoying themselves and the age gap really isn’t a thing. Harry has obviously famously had a thing for older women but he’s just extremely mature himself, you’d never think there was a decade between them.”
Despite rumors that the couple is already moving in together, E! News claimed that this wasn’t the case. An insider told them, “She stays with him when she doesn’t have kids. But she still has her house.”
We can’t wait to see what’s next for the couple!