If you're following the love triangle that is Jason Sudeikis, his ex-fiancée Olivia Wilde, and her new boyfriend Harry Styles (ever heard of him?), there's been a ton of speculation about what happened. We first learned of the Sudeikis-Wilde split on November 13, 2020, but the statement said they'd broken up earlier in the year. Literally that same day, Wilde praised Styles for being "a man with confidence" and "extraordinary," since the two would be starring in (and Wilde would be directing) the upcoming thriller Don't Worry Darling. The first photos of this new Wilde-Styles (Wiles?) pairing appeared in January 2021, when they were pictured holding hands at Styles's agent's wedding.
Sudeikis and Wilde were engaged for more than seven years and had been together since November 2011. The two are currently in London as part of the same quarantine "bubble" but living separately (Wilde is, apparently, living with Styles and the relationship is "very serious"; Sudeikis is filming a new season of Ted Lasso). This is what we know—so far—and when it happened.
April 21, 2021
According to ET, the pair have been spending some much needed "one-on-one" time in London for the past few weeks. Filming Don't Worry Darling was quite draining for the couple, so they opted to take some down time across the pond. "Filming during a pandemic in L.A. was pretty all-consuming," the source said. "Now they're able to unwind, relax, and really enjoy some one-on-one time."
Aside from being spotted on a pub date, the two have generally kept a low profile. "Their idea of a good time is going for a long walk and ducking into a neighborhood pub," the source said.
Jason Sudeikis was also in London for business (presumably finalizing the last season of his hit show Ted Lasso), so both he and Wilde have been co-parenting the two children they share, 6-year-old Otis and 4-year-old Daisy. "All [Olivia's] ever wanted is for them to have a united front," a source told ET. "They are and always will be a family."
April 15, 2021
As reported by The Mirror, Wilde and Styles were spotted at a pub in London after coronavirus restrictions were eased in the city. They dined al fresco and were "grinning like Cheshire cats at each other all night," according to the source. "They looked very cosy on an intimate table for two away from other diners."
"She had her legs crossed and gently nudged against him. They looked completely smitten."
April 1, 2021
After Styles appeared in Gucci's new campaign video wearing an over-the-top fur coat–he's a frequent Gucci ambassador and connoisseur of retro 'fits–the internet lit up with memes comparing the musician to Alison Janey's signature coat in the film I, Tonya. Wilde eventually got wind of the fun after writer Evan Ross Katz posted the memes on his Instagram. "Need a cinematic universe where it's Harry Styles and Allison Janney in bulky fur coats. We can figure out plot details at a later date," Katz captioned the post.
Wilde commented on the post with the crying laughing emoji.
March 16, 2021
In a post on her Instagram story, Wilde slyly congratulated Styles for winning a Best Pop Solo Performance Grammy for his smash hit "Watermelon Sugar." She shared an image of a leather-clad Mick Jagger–a reference to Styles' internet breaking leather ensemble that he wore at the award show–along with a picture of Paul McCartney biting into a massive slice of watermelon. It doesn't get much more obvious than that!
March 8, 2021
As reported by Page Six, Styles headed to L.A. to film a performance for the Grammys. Wilde and Sudeikis are both in London. The two "form a bubble to co-parent their kids." Per the same source, “Jason is still heartbroken over their split, but they are keeping things amicable for their kids. They still care about each other and are friendly, despite her romance with Harry.”
March 7, 2021
Sudeikis won a Critic's Choice Award for Ted Lasso and thanked Wilde and their children. "I want to thank my kids, Otis and Daisy, and I want to thank their mom, Olivia, who had the initial idea for this as a TV show...She was like, 'You guys like doing that so much, you should do it as a movie or a TV show,' and she was right!"
Wilde responded by tweeting her congratulations, and making a sly, funny reference to the fact that Sudeikis has been accepting awards in hoodies:
March 4, 2021
Sources confirm Sudeikis has a new relationship with model/actor Keeley Hazell after online sleuthers spotted her decor behind him while he was accepting his Golden Globe win for Ted Lasso. A source denied the rumor they were living together: "Jason has not moved in with Keeley. He remains still heartbroken over Olivia and isn’t yet ready for another serious relationship."
Apparently, "Jason is very much living with his children, they have been with him the whole time while she was filming [Don’t Worry Darling] and gallivanting with Harry [in LA].” Oof.
February 18, 2021
News breaks that Wilde and Styles had been living together in L.A. "for a while" and headed to England together after they finished filming Don't Worry Darling, where she reunited with her children). On February 6, a source said that the two "seem very serious" and "spend all their time together."
February 15, 2021
Wilde praises Styles effusively in a looooong post about Don't Worry Darling:
Little known fact: most male actors don’t want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it’s so hard to get financing for movies focusing on female stories. No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight. Enter: @harrystyles, our “Jack” . Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our “Alice”, but he infused every scene with a nuanced sense of humanity. He didn’t have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards.
January 15, 2021
Sudeikis is still devastated, apparently. "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...'He’s desperate to' win Wilde back so that they can 'repair their family.'" Oh boy.
January 8, 2021
In a story to People, a source revealed that Sudeikis is "absolutely heartbroken about the split." They added, "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...But what happens next remains to be seen." In another People story, a source said that assumptions about the timing of their breakup wasn't the true story. "Jason feels that the timeline that Olivia and Harry would like people to believe—that she and Jason split ages ago, long before she became involved with Harry—is simply not accurate."
"She began filming [Don't Worry Darling] in September, and by October, he began to get the impression that she wanted out. By November, they'd announced their split." And then this: "But that's how quickly it happened, and none of it happened until she began filming with Harry."
Page Six claimed that Sudeikis and Wilde had recently bought a house in the UK, and that the real breakup happened like this: "Jason found out about Harry and pushed the conversation. Olivia then asked for a separation and news of the split was made public."
Another source refuted all this: "Olivia and Jason were broken up as of early 2020. The recent news that she has moved on is no surprise. Olivia and Jason's relationship continues to be focused on their children and co-parenting them." The next day, a source insists, "Harry did not break up an engagement."
January 4, 2021
Outlets report the first photos of Styles and Wilde, who'd appeared together the previous weekend at his agent's wedding at Montecito, CA. A source clarified to People that they'd apparently been dating for "a few weeks." Apparently they met "organically" on set.
November 13, 2020
People first reports the end of Wilde and Sudeikis' engagement, saying per a source, "The split happened at the beginning of the year...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." (So even though the split was announced November, the original statement makes it seem like the split happened earlier.)
On the same day as the split announcement, Wilde was interviewed for Don’t Worry Darling by Vogue. In it, she said, "[We] 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. And this movie is incredibly stylistic." She added,
"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."
So that...was some really coincidental timing, given what we know now.