Jason Sudeikis Is Reportedly ‘Hurt’ Over Olivia Wilde and Harry Styles’s Rumored Relationship

When news first broke in November 2020 that Jason Sudeikis and Olivia Wilde had split, it looked like one of the cleanest and most amicable breakups in recent Hollywood history. They’d managed to keep it quiet for months, and both halves of the low-key couple were reportedly focused on their kids. But now that Wilde has reportedly moved on with pop star Harry Styles, sources are painting a different picture. 

Sudeikis is reportedly “absolutely heartbroken about the split,” according to a source who spoke to People. “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.” The source added, “But what happens next remains to be seen.”

Meanwhile, a source at Entertainment Tonight says that “[Sudeikis] has been really hurt and somewhat jealous that Olivia has moved on with Harry,” perhaps partly because he thought they “would eventually reconcile and get back together.”

Someone—or multiple someones—spreading rumors of unrequited hopes for reconciliation is one thing, but there’s another wrinkle in this story: the timeline, and Styles’s place in it.

The former One Direction member joined the cast of Wilde’s movie Don’t Worry Darling in September, after Wilde fired Shia LaBeouf. According to one timeline, that was long after she and Jason Sudeikis split (reportedly at the beginning of 2020). But how definitive was that split? According to another source who spoke to People, “[Olivia] and Jason were very much together as recently as this fall,” and  “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.” The implication here seems to be that Styles was part of the reason Wilde wanted out. Said that source from People’s story, “She began filming [Don’t Worry Darling] in September, and by October, [Sudeikis] began to get the impression that she wanted out. By November they’d announced their split…. That’s how quickly it happened, and none of it happened until she began filming with Harry.”

A source who spoke to Us Weekly put it more bluntly. “Whether Harry knows it or not, he was a reason for the split and it blindsided Jason—he totally adores Olivia and is devastated,” they said. Though another source claims, “The engagement was called off early last year, as was previously reported. Harry was in no way the reason for their split.”

So there you have it. He reportedly said; she reportedly said. None of the three people involved have directly commented on the matter, so we don’t really know anything concrete at this point.