Jason Sudeikis is ‘still heartbroken about Olivia & Harry’s relationship’

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Early January, we learned that Olivia Wilde had started dating Harry Styles. Their relationship began weeks, perhaps months, earlier, when she directed Harry in Don’t Worry Darling. Their relationship came as a surprise to Jason Sudeikis, who had been Olivia’s partner/lover/baby-daddy for years, only to see that relationship fizzle last fall. While Olivia ran around claiming that her relationship with Jason had been pretty much over throughout 2020, sources claimed that Jason felt strongly that Olivia had dumped him as soon as she began working with Harry.

All of that began a strange era in gossip around Jason, as “sources” ran around telling Entertainment Tonight, Page Six and Us Weekly that Jason was and is hurt, jealous and not over Olivia. They said he wanted Olivia and Harry to break up so he and Olivia could work on their relationship. It was all surprisingly melodramatic. I’ll be honest: most of it read like Olivia’s version of how Jason felt, at least to me. Soon after Olivia and Harry wrapped on Don’t Worry Darling, Jason went to the UK to begin filming Ted Lasso Season 2. Olivia came with him, because of their kids, and because Harry lives in the UK. They’ve all been in London for months now. And so… we’re getting another story about how Jason is torn up about Olivia’s relationship with Harry?

Jason Sudeikis remains anguished about ex Olivia Wilde’s romance with Harry Styles, Page Six is told.

“Jason is still heartbroken about Olivia and Harry’s relationship,” a source familiar with the situation said. “They’re going from strength to strength, and he’s still massively upset and, to be honest, is still a little angry.”

Wilde, 37, was seen snuggling up with Styles, 27, last week at a cozy lunch, followed by a stroll in a nearby park. The comic, 45, is currently filming the new season of his Apple TV+ hit, “Ted Lasso,” in one corner of London, while the musician is filming his new movie, “My Policeman,” in another part of the UK capital.

The actress is also in town with her two kid, 7-year-old Otis and 4-year-old Daisy, whom she shares with Sudeikis. The children are currently dividing their time between parents. Sudeikis, who has been dating British model Keeley Hazell, is due to jet to Los Angeles this week for an Apple special to promote the new season of “Ted Lasso,” for which he won a Golden Globe and SAG Award this year.

[From Page Six]

Maybe I just have a thing about Olivia Wilde (it’s true, she’s not my fave), but again, this reads like her version of events. All of these stories have read like her version – her ex is obsessed with her, he’s jealous of how hot she is and how quickly she moved on, he’s completely torn up because she’s a beautiful princess being courted by one of the biggest pop stars in the world. I mean, if all of that is true, then good for Olivia, I guess. But Jason has been radiating a calm, peaceful energy for months, and I’m pretty sure he’s dating other women in London too. It can be both, granted. He can be dating other people and still be hung up on Olivia. But mostly I think they’re parents of two young kids and they’re trying to figure that out and balance it with their own dating lives.

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Photos courtesy of Avalon Red, SAG Awards.

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37 Responses to “Jason Sudeikis is ‘still heartbroken about Olivia & Harry’s relationship’”

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  1. Laalaa says:

    My impression of her is that she burns bridges with exes. She can’t do that this time, so she is doing this.
    But the argument is so easy to make – he, 45, is watching his ex dating a 27 yo. Like, of course he’s not completely okay with it, it’s still fresh

    • Darla says:

      Oh that’s true, Harry is only 10 years younger than Olivia but he’s nearly 20 younger than Jason, that’s gotta burn. I don’t know who’s leaking this though. Maybe it’s just made up. Who knows.

    • Jennifer says:

      She definitely doesn’t burn bridges. Her and her ex husband Tao are still close friends and he commented on her birthday posts from this year. Jason gave her a shout out at the Critics Choice Awards this year after they broke up and she responded sweetly on Twitter. Her twitter activity seems to suggest she’s even friends with Jason’s ex wife who he was married to before her. I think this is all tabloid gossip. Her and Jason seem to be on good terms and have been spotted hanging out with their kids and alone since breaking up.

  2. Princess Peach says:

    She honestly seems like such a narcissist. Her partner being insecure was the reason she claimed her marriage ended too. Like it seems odd that every one of her long term relationships end with absolutely no fault of her own. Reminds me of the Middleton “never put a foot wrong” PR.

  3. ThatgirlThere says:

    He may be sad about the relationship ending but I think he’ll be fine. I remember reading how said that she though she wasn’t cool enough for Jason. I think his ego is healthy enough to think he could still pull a hot girl.

  4. Wilma says:

    It’s probably messy because ending relationships and having children together is inevitably a bit messy, but they seem to be committed to making it work for their kids.

  5. Lena says:

    I wish their ‘sources’ would stop running to the tabloid press to tell us details. Just like Againifer I wish they would just show us their pap pictures & let us fill it in ourselves. He’s seeing a beautiful blonde now I’m sure he’s getting over Olivia okay.

    • Jules says:

      Againifer, dying!

    • Tiffany :) says:

      Tabloids don’t have to have actual “sources” to print something. They make semi-logical assumptions and run with it. It’s been this way for decades! They assume someone in the breakup will have hurt feelings, and pick a narrative.

      I don’t think we should assume this comes from Olivia’s camp.

      • Myra says:

        People always forget this part or that paparazzi actually gets tipped off without being called by someone’s agent.

      • Meg says:

        In other cases yes but this message is olivias MO. She did this with past relationships. Her PR team works overtime for her

  6. Case says:

    Coming from the perspective of Team Nobody (or Team Kids), I feel like there’s a real bias against Olivia in a lot of these articles/comments. I mean idk maybe she really is an ahole – I truly don’t care personally about either of them enough to know — but it seems like people like his Ted Lasso character and therefore think he’s definitely the victim and isn’t playing his own games in the media (which…I feel like they both have been).

    • Oy_Hey says:

      This – all day this. There are no facts or even tabloid stories that these comments are coming from. Its all just people’s “feelings”. Like could you imagine the comments if this story replaced Jason with Brad and Olivia with Angelina? People would rightfully flip. Its just so much internalized misogyny .

    • Meg says:

      Posts here mention previous efforts from olivias team to control the narrative to paint her in a positive light, her exes are always pining for her and jealous, the relationship was over long before we knew so she didn’t cheat etc. Shes said this before

      • Darla says:

        well, maybe her exes are all pining for her. My exes have pined for me and she’s more beautiful. It’s not a stretch.

  7. Twin falls says:

    I just watched Ted Lasso over the weekend and I LOVED it.

    It’s not much of a story, after a break-up one party still has feelings about it, but I’ll take it just to be able to talk about Ted Lasso.

  8. Destiny says:

    They weren’t married. She wasn’t in love and did the decent thing and broke up with him. Why is this a bad thing???

    • Cava 24 says:

      Yeah, there’s this weird foundational thing of “well he was happy and (supposedly) crazy about her and therefore she is terrible for leaving him” in some of these articles that I don’t get. If the relationship is not working for her, she doesn’t have to stay in it. It’s not up to him to solely decide if the relationship was working.

      • Darla says:

        ^^^Two great comments here.

      • Case says:

        Totally agree. I don’t get the protectiveness over Jason in this situation. They split up, she moved on, and it sounds like he did too. I don’t understand the problem.

    • Myra says:

      I thought they were insinuating she cheated on him with Harry. So they simply separated and he hasn’t been able to move on? I know it hurts but it’s always for the best if one party breaks up with the other before the cheating happens. There’s no point in staying in an unhappy relationship.

  9. Amelie says:

    I was gonna say he should move on with a cute British celebrity and it seems he already has! I googled Keeley Hazell because i have no idea who she is and I don’t know anything about her and she seems cute. My one worry was her age but she is 34 and Jason is 45 so she isn’t some 21 year old just barely legal adult.

  10. Courtney says:

    He always looks so aloof and unmoved by her in pictures. I think this is a situation where she felt taken for granted and Harry made her feel special at a time when Jason didn’t seem to give a damn.

  11. KinChicago says:

    Doesn’t have to be one versus the other. They are all talented, sure to thrive professionally.
    I am guessing with covid pandemic restrictions ending, all parties are going to get out, move on and hopefully get past all this for the greater happiness of all parties.
    Including the kids.

  12. pottymouth pup says:

    honestly, it would not surprise me that he was completely broken up about the split & kept pushing to try to work things out with her. I remember watching his episode of who do you think you are & the men in his family line have a long history of abandoning their families and it struck me that he wanted to provide his children with a stable family life so it would make sense that he’d struggle with his partner seemingly tapping out with a jump off at the ready.

  13. MyHiddles says:

    He should be thankful the trash took itself out.

  14. SM says:

    All those “messages” in the press do come from someone, and yes, it seems like those come from her, just like the other portion of her being romanced by the one and only – Harry Styles, which felt like a form of bragging. I do not see Jason (even if he felt that way) leaking this to the press, not I think he goes around pouring his heart out to people, who then, in turn would run to the press. I mean, a guy who wears that moustache and turns up to award events stoned wearing fluffy sweaters does not seem like a guy who would be obsessing over anything really.

  15. Meime says:

    I mean…maybe he feels this way…or maybe she’s annoyed that he’s seeing someone new and doesn’t feel this way anymore? IDK. She’s pulled this stuff in previous relationships, yes? I can’t be bothered to Google it, but she always struck me as a “Cool Girl,” and I’ve always really liked him, so he actually elevated her for me. She is very talented though. I won’t deny that. Regardless of her personal life or whether she’s an a run of the mill ahole in relationships. I loved Booksmart. And I will watch the new movie when it comes out.

  16. Anne Call says:

    Don’t really care what these two adults do, but it must be so confusing for kids to go through all this. I’m sure Harry Styles is a nice person, but at 27 I find it hard to believe that he wants to become a surrogate daddy. I know it happens all the time, but it really makes me appreciate my uneventful stable growing up years.

  17. Justjj says:

    I think Olivia was an a hole in this situation and we have been hearing stuff from her side for months about how she’s beautiful and desirable etc. and she needs to chill. Jason will be fine. He’s very cute. She’s pretty, but I mean, this is over the top with all this he’s obsessed rhetoric…