Jason Sudeikis and Olivia Wilde broke up and ended their engagement at some point in 2020. Sources close to Olivia insisted that they were over in the summer or early fall of 2020, and that she was free and clear to fall for Harry Styles on the set of Don’t Worry Darling in the fall of 2020. Jason’s version of events is that he and Olivia split in November 2020 and Harry Styles was the third party and the reason why Olivia left him. Earlier this year, “sources” were going wild, assigning blame all over the place. It’s settled down a lot in the last half of this year, possibly because Jason is dating other people now too. Over the summer, he was seen out with Keeley Hazell, who plays “Bex” in Ted Lasso. Over the Thanksgiving holiday, Jason and Keeley were in Cabo together:
Jason Sudeikis reignited his romance with former glamor model Keeley Hazell “because he feels safe with her,” following the heartbreak of his split with Olivia Wilde, according to sources. Insiders say earlier this year the relationship between the former “Saturday Night Live” star and British model and actress Hazell had been more casual. But after the pair were caught kissing on a beach in Cabos San Lucas, Mexico, earlier this week, an insider says that British former Page Three girl Hazell is hoping to take her relationship with the 46-year-old “Ted Lasso” star to the next level.
The insider said, “Jason was and still is devastated over his split with Olivia; she’s the mother of his kids. But he has known Keeley for a long time, and he feels safe and relaxed with her. They enjoy each other’s company.”
The insider added Sudeikis’ friends were not initially sure how long his relationship with Hazell would last — because he wasn’t looking for anything serious after his split with Wilde — but they are happy he seems happy with Hazell.
“Keeley has really helped him through his split with Olivia,” the source added.
Their friendship goes back a long way: Hazell spent time with Sudeikis on the set of 2014’s “Horrible Bosses 2” where she played Chris Pine’s assistant. But the insiders say, before that, they already knew each other through friends in Los Angeles. The source added, “Jason met Keeley through friends in Los Angeles. But she now lives in London, where of course he films ‘Ted Lasso.’” He is expected to return to the UK in early January to continue filming the show’s third season.
I suspect that Jason and his PR wants everyone to know that while Jason and Keeley have been friends for years, they only became romantic over the summer, months after Olivia “left him.” That might even be the truth, who knows. While I think Olivia Wilde is kind of chaotic in relationships, I’m uncomfortable with the “Olivia left Jason for Harry” narrative which Jason seems to be pushing hard. I feel like it was way more complicated than that.
— Page Six (@PageSix) November 29, 2021
Photos courtesy of Instar, Backgrid and SAG.