Jason Sudeikis hopes that Harry Styles or Olivia Wilde will end their fling soon

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In an earlier post, I suggested that perhaps Olivia Wilde and Jason Sudeikis are pretty bland, and that’s why they’ve become the blank canvases on which people are projecting increasingly wacky opinions. I still believe that! But I’d also like to point out something else: at no point did anyone say that everyone is required to have a strong opinion about Olivia Wilde maybe-probably dumping Jason Sudeikis just as soon as Harry Styles came around. You can literally sit there and read the stories and NOT have to be “Team Wilde” or “Team Sudeikis” or even “Team Styles.” In fact, you’ll probably enjoy the stories more if you just dismiss all three people as messy and melodramatic.

So, yeah, that’s where we are now – Olivia set the narrative about how famous, beautiful, desirable and in-demand she is and how Jason was uncomfortable with that. Then Jason pushed back as soon as Olivia pap strolled with Harry and said that Olivia lied to him and their relationship fell apart as soon as she met Harry. Team Wilde counter-punched with a story about how Jason is just “jealous” because she’s moved on. Now, I guess Team Sudeikis wants us to know that he thinks Harry will end up dumping her.

Harry Styles fans were heartbroken when photos emerged of him holding hands with Olivia Wilde, but no one was more upset about the new relationship than her ex-fiancé, Jason Sudeikis.

“Jason’s had no option but to step back and let Olivia do her thing, but he [has his fingers crossed] that this is just a phase and that Olivia will snap out of it or that Harry will get bored and move on before too long,” a source exclusively reveals in the new issue of Us Weekly. “He’s desperate to” win Wilde back so that they can “repair their family.”

Sudeikis, 45, and Wilde, 36, who share son Otis, 6, and daughter Daisy, 4, had been dating for nine years and were engaged for seven when Us confirmed in November 2020 that they had called it quits. However, the timeline of their split has continued to make headlines since she and Styles, 26, went public with their budding romance earlier this month at the “Watermelon Sugar” singer’s manager Jeffrey Azoff’s wedding.

[From Us Weekly]

Is it mean to admit that I think those are really the only options as well? Either Olivia is going to snap out of it and realize that Harry looks prettier than her in a pussybow blouse and dump him OR Harry is going to move along. I tend to believe Harry will move along, probably a month or two after they wrap on Don’t Worry Darling. I could be wrong! I think Harry seems like a sweetheart, but I also think he’s at the point in his life where he doesn’t want any part of this Wilde-Sudeikis melodrama. Shades of his Taylor Swift fling, remember? She was so extra during their thing and after and he was so completely over it.

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56 Responses to “Jason Sudeikis hopes that Harry Styles or Olivia Wilde will end their fling soon”

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  1. smee says:

    I sincerely doubt she thinks this a long-term situation with HS
    More like an “inspiring” way to gtfo of a dead, long-term relationship. I would be surprised if they reunited, but what do I know!

    • Nev says:


      what do we know?
      if he’s waiting and then they reunite, what if it happens again?
      is this what it is?

    • Wiglet Watcher says:

      There are better ways to exit a long term relationship with children. Like, just being honest and not having a jump off you need to hide from your fiancé.
      Harry is probably going to move on.

      • Delilah says:

        “There are better ways to exit…like being honest”…you’re right, the exception being, not when 1 partner is still into their ex.

        All said pining dumpee wants is to have their partner back. They are not in a place to accept it’s over. They’re in denial. None of the “it’s over” message transmits to someone unwilling to accept reality, especially if still in love.

        This is why wronged parties sometimes take their exes back. All they want is them. Right and wrong or pride be damned! I absolutely believe Jason would take Olivia back no matter what.

      • whatWHAT? says:

        Harry Styles is a gorgeous rock star who is still very young.

        this won’t last long, I’m sure.

    • Still_Sarah says:

      @ Smee : and “the affair” is great promotion for OW’s new movie “Hello Darling” which nobody was noticing before the alleged scandal. Yawn. Typical PR move, I think.

  2. AlpineWitch says:

    “Jason’s had no option but to step back and let Olivia do her thing, but he [has his fingers crossed] that this is just a phase and that Olivia will snap out of it or that Harry will get bored and move on before too long,”

    If this is true, he comes across as pathetic. Even if she gets dumped, why should she go back to him? I hope those sources aren’t as close to him as they want us to believe.

    • Merricat says:


    • emma33 says:

      Yeah – and if he’s really just waiting this out,, how is spelling this out to the whole world going to help? It’s kind of pathetic, and is just going to make her annoyed. Also, probably reminding her of why she’s with Harry in the first place.

  3. Libellule says:

    I think i’m going to watch this with a glass of prosecco and maybe some sweet potato fries. This is soooo messy, it’s fun

    • Lightpurple says:

      Exactly. I could never stand Jason or Olivia so this is just delicious. And Harry Styles is not going to stick around for this.

      • Dria says:

        I think they both need to stop talking, for their kids. But on the other hand, this is the most the public has talked about either one of them, so maybe they’re enjoying it. Harry definitely seems to enjoy the drama at first, but I think he gets tired of things fast. Him and Olivia should have just hooked up quietly, still have no idea why they went all out for something that’s not clearly going to last.

    • SarahCS says:

      I’m very much enjoying the drama from the sidelines. I have no horse in this race but I do enjoy gossip (why else would I be here).

  4. Lucy2 says:

    I feel like us weekly is probably exaggerating a lot of this, due to the lack of other celebrity news right now.

    • Tiffany :) says:

      Exactly, Lucy. The tabloids invent people’s “feelings” all the time. They just fill in the gaps around what is known (they’ve split) with things that are believable. That’s standard procedure for US tabloids.

  5. Snuffles says:

    Harry could very well be a temporary (and DELICIOUS) fling. A passive aggressive way of letting Jason know she’s done with him. I seriously doubt she’s going back to him.

  6. Daisy says:

    I honestly think 90% of those stories are exaggerated. But if it’s really coming from Jason’s camp, they need to chill a bit. It’s just making him look pathetic.

  7. sassy pomeranian says:

    Yes, this is second hand gossip (about 5 years ago) but my friend lived in their building in NYC and said Jason would always bring home women late nights, whenever Olivia was out of town. He said it was pretty messy.

    • Julie says:

      I also have a pretty reliable third party account that has Jason as a dog a few years ago. I gathered this was why they never actually married. I actually think that HIS cheating was the real basis for the breakup. I think Jason got busted again in early 2020 and Olivia didn’t break it off cleanly but rather seemed to be allowing him space to redeem himself. Basically they were occasionally hooking up as recently as late 2020 but not fully reconciled. I even think they set up separate living arrangements but it was nebulous since they were still hooking up. He was just blindsided that the breakup stuck.

      It would explain why they have differing narratives of their couple status.

      • Normades says:

        This makes total sense to me.

        I think Olivia and Harry will last 2 years.

      • Xoxo says:

        I don’t think cheating was a factor or matter to them. Olivia gave a whole speech about how in Olivia land she would normalize hiring “clean” sex workers to satisfy her partner.

      • ennie says:

        One thing is an honest open to others relationship/marriage, and another dishonesty. Who was dishonest here, only they know.

    • Tiffany :) says:

      Yikes, that’s not good if true.

    • Lizzie Bathory says:


  8. LaurenMichelle says:

    This is all very entertaining and has made me forget about Ben & Ana! Harry has a beautiful voice and is very charismatic.
    He also comes from a stable family and tends to treat women very well.

    Harry actually is good for Olivia’s image, and makes her seem more relatable. Jason and Olivia together are the Smug Twins and burned eachother out with their smugness.
    Stop blaming sweet Harry!

  9. Sean says:

    To be honest, I’m loving this drama as a distraction from the realities of what is happening in my country (USA). Does that make a bad person?

  10. TheOriginalMia says:

    Have some pride, man. She left you. It’s over.

    • AnneSurely says:

      Seriously, this is embarrassing. Alternatively trading on misogynistic tropes and pathetic whining. If he really wanted to play the game, he could find someone cool, single, and childless in Olivia’s age range who needs some exposure in stead of this sad man baby shit.

  11. Tuntmore says:

    I think people need to lay off Jason a bit. This is a fresh wound — the end of a long relationship in which children are involved. I don’t think wanting your ex to “smarten up” and come back is pathetic, not when he’s only had weeks to process it. If he’s still waiting for her to come back after a year, then it starts to become pathetic.

    I love Harry, but I think this is a fun short-term fling for him and Olivia. That doesn’t mean she’ll reconcile with Jason once it’s over. It sounds like she’s been done with the relationship for a while.

    • AlpineWitch says:

      No, he’s definitely either pathetic or manipulating the public. If you read above, there are accounts of him cheating over the years and it might have been a case of ‘she left, only I could’ case. It doesn’t paint him in a good light, regardless of the fact there are children involved (also… I remember all the gossip about him, January Jones and her kid.. I always side-eyed him after that).

      • Tiffany :) says:

        We need to remember that tabloid stories that are sympathetic to him don’t necessarily come from his “camp”. I can see why people make that assumption, but a lot of times tabloids form a narrative without help from either party.

  12. Emily says:

    Speaking in Taylor Swift metaphors, Harry ‘s love is red, Jason’s must be blue and Olivia needs to find a love that’s golden 😛

    Joking aside, Harry will 100% move on. He’s a nice guy but he’s also strikes me as being very free love and not a step daddy type.

  13. Cava24 says:

    This is actually a sick burn from Jason, it sets up the idea that Harry “got tired of her” if she and Harry break up. Which they will do. Who knows when they will break up but this was partially fueled by having the cast/crew of that movie in a pandemic pod and those two crushing on each other in a work setting- they have no idea whether normal life is going to suit them. And their work product – his recent video, their film, is totally getting overshadowed by this.

    Jason does not want her back, he wants her and Harry to break up so he can tell people she tried to come back to him and he rejected her.

    • J.Mo says:

      Your observations are spot on, except I think he is setting it up to look like he let her come back after she gets dumped or comes to her senses.

  14. Wilma says:

    I love both Harry Styles and Jason Sudeikis. I’m hoping for a bromance after they put Olivia behind them. But, I also always believed Aniston and Jolie should have both forgotten about Pitt and do a project together so what do I know.

    • Dria says:

      Honestly, I think Harry and Jason would be a cuter couple than Olivia with either one of them.

      And so would Angelina and Jennifer. Very opposites attract, but both hotter than Brad.

  15. Lory says:

    This is LITERALLY the first time either have them been remotely interesting and it’s all because of a Harry Styles. They should both thank him for raising their profiles.

  16. Lillyfromlilooet says:

    Oh, Jason, honey. She’s not coming back to you.

    @kaiser you are right–the whole point of gossip is to project–I got a blissfully peaceful life and an active mind looking for intrigue.

    • Amanda says:

      Exactly. I don’t see her and Harry lasting, but I don’t see her going back to Jason either.

  17. Jessie says:

    She has said in an interview back when she got with Jason Sudeikis, that after a while in a relationship you vagina just NOPEs at the person you’re with and that’s how you know it’s over, no matter how fond of them you are.

    Pretty sure him publicly begging like this will not bring back her vagina.

  18. NYStateofMind says:

    It’s new sex. Period. They won’t last but she will never go back to Jason. She could have handled it in a better way. Pretty shitty of her.

  19. Valiantly Varnished says:

    I mean…he’s right. There is a 10 year age gap between them and Olivia has two kids and is fresh out of a long term engagement. That’s a lot for a 26 year old single dude to take on. And I think the moment it stops being fun, Harry will bounce. And I can totally see Olivia just going back to Jason. All of this sounds likely to me.

  20. Marigold says:

    I don’t think wanting your family back is pathetic. That is such a weird take. That shows that he is human. I went through a divorce when my children were young and I had dreams about my family getting back together for years. Why do we label men or women as pathetic when they show real human emotions. Would we rather have had him be a jerk about it?

    • whateveryousay says:

      Yeah. There’s a lot of ugliness coming from some of the comments here. If this was Olivia and Jason had ran off with Demi Lavato or someone else like that everyone would be up in arms.

  21. L4frimaire says:

    Why is everyone assuming this is serious for Wilde? She has two kids, seems busy enough, and has to coparent with Sudeikis. Maybe she just wants to be with someone who is fun, cute, won’t interfere in her family life and won’t make commitment demands on her, because they’re both busy with their respective careers. He’s too young and she’s just got out of a long term relationship. Her ex needs to take this conversation offline and mind his business. Can’t believe how this has blown up but the sexism and double standards is just bothering me.

    • AnneSurely says:

      Right? This is a othing serious since she has a ton of responsibilities. Heaven forbid she want to have some fun after what I can only imagine was a slog with a whiny manchild, considering the way he’s reacted to this. She is for sure not looking to put a ring on Harry Styles. Some times this site goes way overboard on misogyny.

  22. HeyJude says:

    I’m going to go against consensus here- Olivia and Harry could go on for a few years. They’re both about the same kind of weird. Harry’s getting to an age where flings are losing their luster. They can share interests. They can shop for loud blouses together. He can shop for absurd amounts of rings to wear at once, while she shops for absurd amounts of earrings to wear at once. They both got that “oh we’re bohemian artistes!” thing going on.

    But more practically- Harry wants to be a serious actor, Olivia is the next big up-and-coming woman director. She’s been anointed, she’s got a Marvel deal to prove it. She opens doors, will have roles to hand out, and will be able to let him mingle with big movie execs. Harry might see benefit there. She might see the benefit in a guy with headline press ability. And she got her director’s standard package of a young, pretty starlet partner in him.

    • Julia K says:

      Quid pro quo? You have nailed it.

    • J.Mo says:

      I foresee a blouse label and maybe jewelry making lessons? Possibly a sofa, drapes and velvety cushion empire. I don’t think I’m even being facetious anymore.

    • Cava24 says:

      He’s already in The Eternals (at least according to rumor) and has one other film lined up. I don’t think there will be any industry parties for them to make an appearance at for quite awhile. The earliest would likely be the fall film festivals – Telluride, Venice, Toronto and New York and then they would only be going if Don’t Worry Darling is chosen for the festival, in which case the rest of the cast will be there as well and he would only go if it doesn’t conflict with his tour.

    • “they can shop for loud blouses together” omg dying. 🙂

  23. L says:

    His comment is so rude- he is saying Olivia is boring! Now im no Olivia Stan, don’t even like the woman, but why would she want to go back to a man who disses her in the press? If he wanted her to stay with him for life, he should have married her, wtf is with this long term engagement??? Thats not how it works.

    Losers gonna lose JASON.

  24. Dana Dayen says:

    He deserves the misery coming his way as punishment for all the dog shit movies he has helped inflict on the world.

  25. Kelly says:

    I think some is true some is made up by media to sell magazines . I think they broke up about March and were already living in different houses . I think she finally announced it cause she wanted to start dating again ! It was announced on nov 13 that they broke up earlier this year if Jason was upset he would of said wait no we didn’t right then but they were living in separate houses . Then when Olivia and Harry went to wedding he got mad doubtful