Earlier this month, news broke that Olivia Wilde and Harry Styles were dating, nearly two months after it was announced she and longtime fiancé, Jason Sudeikis, had split.
At the time, it was reported that Wilde and Sudeikis’ breakup was amicable and that they remain on good terms with each other as they “transition into a co-parenting routine” and navigate a new normal. However, insiders are now claiming that Sudeikis was blindsided by the split, claiming Wilde had formed a connection with Styles right before calling off their engagement.
Jason Sudeikis and Olivia Wilde broke up in 2020
For years, it seemed like Sudeikis and Wilde were going to be together forever.
The couple first met at a Saturday Night Live afterparty in May 2011 but didn’t start dating until six months later.
“I actually came off looking a little cooler than I really am because I had heard through the grapevine, through mutual friends who weren’t exactly her best girlfriends, who would report back, ‘Oh you know, I think she’s dating someone,’” Sudeikis told Stephen Colbert in 2017. “So I didn’t make any moves. I was just very, very busy with other things. And next thing you know, I stopped being busy, she stopped dating someone, and then it was off to the races.”
As Wilde tells it, she and the actor just kept crossing paths after their initial meeting. “Over the next six months we kept running into each other,” she shared with Allure in 2013. “[One night], my best guy friend walked up to him and said, ‘This is Olivia’s number. Use it.’ That was the beginning.”
After two years of dating, the Horrible Bosses star proposed to Wilde in January 2013. Later that same year, the Tron: Legacy actor became pregnant with their first child.
In April 2014, Wilde gave birth to their son, Otis, and two years later, the couple welcomed their daughter, Daisy.
From then on, it was clear Sudeikis and Wilde were truly in love with each other. But like many other celebrity romances, their relationship eventually fizzled out as the pair went their separate ways in early 2020.
“The split happened at the beginning of the year,” a source told People in November. “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.”
Olivia Wilde and Harry Styles recently sparked romance rumors
A few weeks after it was reported that Wilde and Sudeikis had split, the Book Smart director began sparking romance rumors with One Direction singer Harry Styles.
According to reports, the pair struck up a close friendship while working together on the upcoming film, Don’t Worry Darling. Their connection soon turned into a romance, which they reportedly kept under wraps until the beginning of January 2021, when they were photographed holding hands at a friend’s wedding in Montecito, California.
“They were affectionate around their friends, held hands and looked very happy,” insiders told People. “They have dated for a few weeks.”
Is Harry Styles the reason Olivia Wilde and Jason Sudeikis called it quits?
Back in November, it was reported that Wilde had kicked off a romantic relationship with Styles while on the set of Don’t Worry Darling.
But insiders now tell The Post (per Page Six) that the actor’s relationship with Styles has actually been going on as far back as October, which has reportedly left Sudeikis distraught.
While there were reports that Wilde and Sudeikis split in early 2020, separate sources say that the couple actually broke up in early November — and cite Wilde’s relationship with the singer as a reason for the split.
“Olivia called off the engagement in early November but only after she already had gotten close to Harry,” an insider tells Us Weekly. “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, a second source claims Sudeikis and Wilde broke up at the beginning of 2020 and notes that Styles “was in no way the reason for their split.”
But whether Styles was the cause of Sudeikis’ split from Wilde or not, the Saturday Night Live alum is still “really hurt” by his ex’s new romance with the singer.
“Olivia and Jason ended amicably and both wanted to remain close and stay friends for the sake of their kids and because they have mutual respect and love for one another,” a source revealed to Entertainment Tonight.
The insider adds that Sudeikis had hoped he and Wilde “would eventually reconcile and get back together.” But seeing as that might not happen now, “he has been really hurt and somewhat jealous that Olivia has moved on with Harry.”
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