People: Olivia Wilde & Jason had ‘problems’ before Olivia started up with Harry

Here are some photos of Olivia Wilde out and about in LA on October 24th. Despite my predictions that Olivia and Harry Styles would be done as soon as the Don’t Worry Darling promotion was over, they are still together. I always thought that Harry didn’t go for this kind of romantic messiness, but maybe he’s changed. Olivia telegraphed their romantic status in these pics by wearing a “Harry’s House” hoodie. Clever merchandising. Anyway, Olivia and Jason Sudeikis’s former nanny kind of ruined Olivia’s big argument/lie that she didn’t cheat on Jason with Harry, and that she and Jason were done long before she met Harry. Throughout DWD’s promotion, Olivia kept insisting that no, of course she didn’t cheat on Jason with Harry, she would never. Except that she absolutely did. So here’s Olivia – excuse me, “a source” – telling People Magazine once again that Jason and Olivia were having problems long before she started banging Harry.

Problems between exes Olivia Wilde and Jason Sudeikis predated the Don’t Worry Darling director’s romance with Harry Styles, sources say.

“There is no easy way to end a long-term relationship,” a source tells PEOPLE in this week’s issue regarding claims the couple’s former nanny made in an interview with the Daily Mail. “There were issues between them before.” Adds the source, “Regardless of what anyone else says about their relationship, nobody but the two of them know what went on and why they split. Jason and Olivia are co-parenting and doing fine with that. The custody issues between them from before have not gotten in the way of both parents being with their kids.”

A separate industry source says despite the breakup, the exes are united in their co-parenting priorities involving daughter Daisy, 6, and son Otis, 8.

“Olivia and Jason have pretty much worked things out and are sharing custody of their children in a mature manner,” says the insider. “The split was unpleasant, but they have moved on. They will always have to communicate and be adult because they have two kids together.”

As for Wilde’s relationship with Styles, 28, they are simply trying to move forward peacefully: “Olivia and Harry have a dynamic relationship which is filled with admiration and respect for the other,” says the industry source. The couple, who started dating during production of Don’t Worry Darling, are currently spending time together in Los Angeles, where the singer is playing shows over the next several weeks.

“Harry and Olivia are great. They’re better than ever,” adds a separate source. “They rise above this sort of thing all the time, and they’re just moving forward with their relationship and are happy and thriving”

[From People]

Most of what comes out of Olivia’s mouth is a lie, and this is coming straight from her camp. None of this is true, I suspect. While Jason and Olivia are likely coparenting and trying to dial down the drama, he literally had her served with custody papers in the middle of her CinemaCon presentation. Their filings in their custody fight in New York family court were really rough. And Olivia still plans to MOVE to London with the kids, which is what Jason has been trying to block. Anyway, I kind of think the point of this People story was Olivia wanting to brag about how she and Harry are still in love.

Photos courtesy of Backgrid.

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37 Responses to “People: Olivia Wilde & Jason had ‘problems’ before Olivia started up with Harry”

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  1. Izzy says:

    Why does she think this is a good look? She still cheated. Still lied and moved into a hotel, lying about COVID protocols so she could bang her sidepiece. EVERYONE looks so messy in this. Team Kids.

  2. María says:

    Again with the lies… Hasn’t she learned that it will backfire?
    Just own up to what you did and move on, it’s that simple.

  3. Meredith says:

    I mean. Are we totally sure that Styles doesn’t like the drama? When I look back at the history of posts about him here it kind of seems like he’s almost always kind of been in some kind of drama.

    • Emily_C says:

      I think he enjoys creating drama. He manipulates the hell out of his fans, why should his personal life be any different?

    • lunchcoma says:

      Agreed. He’s not giving gushy interviews with good pull quotes in them, but he’s regularly involved in drama and has dated a series of dramatic people.

      That could mean a manipulator or a victim or someone who just needs to go to therapy, but that’s not a person who avoids messiness.

    • María says:

      I suspect he’s not the most balanced person, he gives me toxic vibes. His sudden breakup with Taylor Swift comes to mind…

      I think he definitely enjoys this whole dating a married person and creating drama.

      • Beach says:

        I agree about the toxic vibes, but how is his breakup with Taylor your main indication lol? He was 18 dating a 23 year old, and they dated for like two months. It wasn’t sudden, they probably just didn’t fit well. Plus, every move if theirs was publicly documented by their teams.

  4. Emily_C says:

    I’ve said it before: If the genders were reversed, people would be screaming incessantly that Harry Styles is a homewrecker. But the queerbaity “teehee look at me I’m so soft really so SOFT so SAFE so SOFT” creep is not being criticized for his role in this at all.

    Not that Olivia Wilde’s innocent by any stretch of the imagination. But come on.

    • Mel says:

      I’m a rarity in that I don’t really believe in homewreckers the problem isn’t the person he/she left you for, the problem is the person who made a commitment and promises to you, who supposedly loves you, didn’t love you enough to tell you that they weren’t happy anymore and they ran off with someone else. So Harry isn’t the problem, she is. I predict that he will dump her by the end of the year. It was all fun and games before but now it’s getting messy, he’s probably thinking, I didn’t sign up for all of this mess……

      • Noxy says:

        Late but I totally agree with this. The home being wrecked is Olivia’s, ergo if anyone is a homewrecker, it’s her (or anyone else who is wrecking their marriage through cheating, male or female). I think it’s s*itty to screw around with a married person period, but the marriage breakdown is squarely on her shoulders. Harry isn’t inside the marriage. I also agree though that if the genders were flipped Harry would be being called a homewrecker (even though I don’t agree).

  5. Red says:

    This is the most Olivia has ever been in the press, of course she’s thriving. You think paparazzi are waiting just to get a glimpse of her walking alone with a coffee? She’s going to make sure she can stay with Harry for a long time. And honestly, Harry does not seem worth all of this.

  6. ThatsNotOkay says:

    This woman actually loves the drama. She feeds off it and wants the world to know she can pull any guy and all these men are fighting over her. Shut up, Olivia.

  7. Kate says:

    Why is drag this out? Move on. All the drama with DWD and her ex has really hurt her standing as a serious director, she has now become a tabloid fixture.

  8. Ann says:

    I still can’t get past that leaked video of her begging Shia to come back to work. The first part where she’s all sweaty cause she just came from riding. Bragging and lying and being a smug ahole all captured in one short video that really locked down the essence of why this woman is such a douche. I hope Jason gets what he wants custody wise and I hope Harry dumps her. The DWD schadenfreude sundae needs a cherry on top.

    • FormerlyLithe says:

      The Shia tape really surprised me. I know there can be a fine line between persuasion and manipulation. But I’m not comfortable with the side of Olivia that tape showed. However I’m also deeply uncomfortable with how anti-woman some of her haters sound. Which makes me feel like a hypocrite for having the feeling that Olivia thrives on attention. Her relationship with Harry will never make sense to me. He never speaks up in her defence but she always seems to be gushing over him.

      • Ann says:

        I’m not anti-women, I’m anti this woman. I do sound a bit too gleeful in her demise though so I will correct myself in saying I hope the custody situation goes as smoothly as possible for everyone’s sake, but especially their kids.

  9. Jessica says:

    If she spent half the time with her kids she spends doing pap strolls and commenting and not commenting on her drama…we’d all be better off. Especially those children.

  10. Lucy says:

    Who are they trying to convince at this point? And why?! God, it’s so boring. Move on with your life, Olivia.

  11. Maddy says:

    When do the Oscar noms come out? I feel like depending on whether or not either of them gets nominated, their relationship could end relatively soon or last through awards season.

    • Beach says:

      What would either of them get nominated for? The movie itself and Harry’s acting were panned by the critics.

      • sunny says:

        The movie was terrible- I got dragged by a friend and generally I love all things Chris Pine but the film was just not good. It was illogical, messy, overwrought, and full of half finished ideas. Not the worst film I had ever seen and visually nice but like mediocre.

        I also saw My Policeman at TIFF. The film is a middling, predictable drama with excellent acting by everyone not named Harry Styles(he is ok but the rest of the cast is very good). So no they won’t be getting nominations for anything but they probably will get invited to awards shows because of the drama they bring.

    • mia girl says:

      I think the only Oscars noms possible for DWD will be creative ones (production design, costume design). No way there are any acting or directing noms.

      I did see yesterday that the People’s Choice Awards is looking to capitalize on the DWD situation by nominating the movie for Best Drama Film and both Florence Pugh and Harry Styles for Drama Movies Star of 2022. I know the PCAs are basically PR/popularity awards, but the Styles nom for acting is ridiculous. Styles is nominated for all the key music awards (and will likely win) so his fandom is already engaged. Why pander by putting him or the film in the drama category?

  12. SquiddusMaximus says:

    Yeesh. Messy, yes, but my hackles rise at vilifying her to the extent we have. Relationships are nuanced; breakups can be complex. May be understandable that by the time she met Harry, she was disengaged from her relationship with Jason while still technically “in” it.

    Sure, we can moralize and tut tut tut that she should have ended it first, but there are kids. And financial factors. And some people (say, a certain squid) have a really hard time plugging the final plug. It ends up being a slow death as opposed to a clean break.

    So I’m conflicted. I don’t care for her much for unrelated reasons, but I’m surprised there is SUCH an anti-Olivia bent in a typically feminist gossip site. Makes me feel hypocritical.

    • diANNa says:

      Thanks for pointing out how Olivia is being vilified here. I don’t really get it either. Her ex has shown by his actions of having her served onstage and by the sad tale shared by the nanny that there were huge issues with his drinking and anger. I find it completely credible that she told him she was moving on and he chose to misunderstand or ignore that.

      • Kebbie says:

        “I find it completely credible that she told him she was moving on and he chose to misunderstand or ignore that.”

        I agree with this. Just because he didn’t accept they were done, doesn’t mean they weren’t actually done.

      • Tiffany:) says:

        Yes, I agree. She also said in a text to nanny that she couldn’t stop by for breakfast kisses with the kids as she always did, because the last time Jason was confrontational and she didn’t want to provoke him further.

    • Twin Falls says:

      +1 to all of this

    • Acclaim says:

      I agree w/ you 100%, squid.


      People, meaning women & men, have the right to want out of ANY relationship they’re in, whether it be with family members (excluding small children shared with a former partner), or with a company that employees them, or with friends and even with any house of worship that they attend.

      We’re human beings, FFS!

      We fall out of love, fall in love, change our minds, or just need a break from things and/or people we may find ourselves questioning.

      This is life!

      Life, at times, even multiple times, is messy AF, and I too, take issue with how this woman is being dragged.

      She may have not had a clean break in this. Perhaps she panicked and f*cked up by lying for reasons only she knows and is aware of.

      SHE KNOWS her ex husband, JS, and is/was particularly aware of their dynamic, and she wanted OUT.

      Ladies & Gentlemen, sometime the ball bounces to a rhythm you may not recognize, or even appreciate, but that’s OK, because the ball isn’t always yours, or even in your court.

      Peace to everyone involved in this and may the kids feel loved, prioritized and cared for by all involved. ❤️

    • sunny says:

      I think any Harry Styles fans were deeply anti Olivia. I think most of Celebitchy responses except for some very pro-jason outliers was that they are both awful. The leaked Shia video however did a ton of damage to OW and the response to posts about her have been increasingly negative since then.

      She seems like a terrible person and has been shown to be a liar repeatedly but that doesn’t mean there isn’t a grey area around this. Couple can have different opinions on when a relationship ended or how healthy/solid a relationship is.

    • Tiffany:) says:

      I agree. So many frame it like she ran off with Styles, but a woman moving into a hotel before she broke it off with her long term partner could be for safety when you know the partner drinks and is volatile.

      Also, people have made a big deal about the “child free” hotel…but it was in Palm Springs, so it was likely paid for by production, and there are dozens and dozens of child-free hotels there because of the clientele the city caters to.

  13. Lola says:

    In my 20’s before I got therapy, I went straight from my mother’s severely abusive household to a much older boyfriend’s household. He had previously dated a woman with severe bipolar who he constantly trashed to me. I was soo different, you see, as I only had crippling anxiety and depression and was meek and unable to assert myself. I didn’t know it but this guy EXCLUSIVELY dated troubled women with severe mental illness. I was the perfect prey for him. Troubled women with severe mental illness are the easiest prey in the world because everyone agrees they are crazy, they struggle to have social connections and friends, and nobody believes them.

    This guy was extremely warped, twisted, and sick, and derived extreme pleasure from non-stop tormenting and provoking my mental illness. He did everything he could to get me to act out or meltdown, the more publicly the better. The most he could get out of me was hysterical sobbing, but that was enough to make me seem unhinged and overreacting to “nothing.” But in his past, and then, in his future, he dated women with different / more severe mental illnesses who were much easier to torture into “acting out.”

    Beware of the “innocent” “empathic” “giver”/”caretaker” types of men who EXCLUSIVELY date extremely troubled or problematic women and are just so constantly mistreated by them as they flip out over absolutely nothing. What patience he has to keep dealing with her as she is just so psycho and horrible to him for no reason.

    I would come home and see that sick smile on his face and know that he would spend all evening trying to get some kind of reaction out of me and literally wouldn’t let me sleep until he got it, which he would often film, and I had nowhere else to go.

    I’m not saying anything here is such an extreme case, but when a person is oh so innocent and just constantly happens to date women who are oh so psycho and awful, that’s a red flag to me.

  14. C says:

    All three of these people are messes. And she needs to get some self-respect and stop doing things like wearing his merch when he barely acknowledges her ever.

  15. HeyKay says:

    I have questions.
    How did OW get to direct a film? I only know her from House and she was only on that a few years. Seen her be full of herself on Letterman. That’s about it. Suddenly she is a director and all over SM, mag covers, talk shows, etc. IMO, she has an iron clad ego, but minimum level of talent.
    She is a cheater, who dumped her kids for a mid-life fling. No class. Just my opinion.
    In 5 years she will be a has-been.

    Harry wants to be a movie star but, the truth is he is hired to pull his fans into the movie just to see him. John Lennon was in a few movies too. Didn’t make him an actor, made him a box office draw.
    Harry has 1Direction $, and he’s touring, not yet 30.

    I don’t find JS funny. Only seen his SNL work.

    I bet OW & JS had “problems” Geez, the info that Nanny gave out….these 2 should have never had kids. Team kids all the way.

    • Sallyhoo says:

      She has been working towards this for a long time… I think she started directing music videos, and shorts, then directed “Booksmart” which was pretty well-received.