Olivia Wilde ‘always seems focused on just making it all work’ with Harry Styles

Olivia Wilde at the tenth annual Art+Film Gala presented by Gucci

It’s crazy to think about how Olivia Wilde and Harry Styles have been together for an entire year. They’ve been papped together at times, but they’re not constantly seen together. Harry has been getting back to a concert schedule, and Olivia goes to his concerts when she can. They went on vacation together in Italy over the summer, and they’ll probably stay together through the promotion for Don’t Worry Darling, the release date of which keeps getting pushed back (and it’s currently set to be released in September 2022). I had the sense that Olivia and Harry were pretty much living together already, so I imagine he’s already spending time with Olivia and Jason Sudeikis’s kids, Otis and Daisy. People Magazine says that Olivia and Harry are taking that part of it pretty slowly though:

In addition to celebrating the holiday season, Harry Styles and Olivia Wilde are about to mark a special milestone: their one-year anniversary. The couple — who initially connected last year while filming the psychological thriller Don’t Worry Darling, starring Styles, 27, and directed by Wilde, 37 — “have a great relationship,” a source tells PEOPLE.

As the couple started getting more serious, the Booksmart director introduced the Watermelon Sugar singer to her two children, son Otis, 7, and daughter Daisy, 5, whom she shares with her ex Jason Sudeikis.

“Harry is slowly getting to know her kids,” says the source “Olivia is also spending time with Harry’s mom.”

The two stars are being mindful about spending time together despite two very busy schedules as Styles just wrapped his Love on Tour, while Wilde finished filming on the period drama Babylon with Brad Pitt and Margot Robbie.

“[They try] to see each other as much as possible,” says the source. “Olivia has been flying nonstop between L.A., where her kids live, to join Harry on tour.” The insider adds: “She always seems focused on just making it all work. She is really Harry’s biggest fan.”

[From People]

I hope Harry flies to see her too, and that he’s expending some time, emotional labor and effort to make this relationship work. Because that’s not the impression I get at all. I get the impression that Olivia is the one flying to see him, that she’s doing the balancing act, that it’s all about her emotional labor. Maybe I’m wrong! To be clear, I think Harry likes Olivia and maybe even loves her. But I think he likes that she’s the one rearranging her schedule for him and not the other way around. As for the stuff about the kids… who knows. I think Jason spends a lot of time with their kids and it’s possible that Harry hasn’t been around the kids that much this year.

63rd Annual GRAMMY Awards – Telecast

Olivia Wide working on the Abs

Photos courtesy of Avalon Red, Backgrid.

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71 Responses to “Olivia Wilde ‘always seems focused on just making it all work’ with Harry Styles”

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  1. Queen Meghan’s Hand says:

    Hmm…something isn’t adding up. Why do we need updates on this relationship? Also, how can Harry be “slowly getting to know” her children if he’s on tour and their with their father half of the time?
    I wish Wilde would try to keep her fame by producing good work and not selling this relationship for more than what it is.

  2. Merricat says:

    I do not understand the animosity people have toward Olivia Wilde. Is it because she’s so much older than Harry? Mr. Merricat is 8 years younger than me, and we’re celebrating our Silver Anniversary in the spring, so I don’t think their relationship is weird or inauthentic or whatever. I also don’t think she is “selling” anything about this relationship, since they’re both pretty private.

    • Wiglet Watcher says:

      I think a lot that plays against her is her PR strategy of trashing her ex’s in the tabloids while praising herself. That and how she has jumpoffs.
      If nothing else, she overshares. All celebs that over share aren’t very likable.

      She’s not a mega celeb. She could fly under the radar and not have her relationships play out on the press. She chooses not to.

      • Merricat says:

        Lol, she is typically pretty private. I don’t know, if there are no news stories about them, people say “Oh, they must be splitting up.” I don’t think what people expect of her is the same of what they accept from other personalities.

      • Wiglet Watcher says:

        Agree to disagree then?
        Only because she gives many interviews oversharing her relationships at the beginnings and the ends. The middle, yes, she’s private. But the beginning a and ends, good lord she needs her narrative out there.
        I feel people wouldn’t be as forgiving if she was a man speaking of how bad his ex wives were.

    • Pilar says:

      Maybe his fans have animosity towards her because of age but speaking for myself and WOC I know its because she epitomises performative white feminism . Also a history of homophobia. People don’t really have a problem with badass older women like Lisa Bonet or Marisa Tomei who marry or date younger men. That said I doubt anyone but his fans have animosity towards her it’s just more that people object to her being presented as someone groundbreaking woman director when she really is a pretty average talent but has been helped by growing up wealthy and connected.

      • Merricat says:

        I’ve never heard anything about a history of homophobia, and I think Harry would not be interested in someone who is homophobic. I also don’t know about her “performative white feminism,” but I do know that if her talent is average, the hype won’t matter, but if you don’t hype, you don’t believe in your project. That’s my opinion.

      • Pilar says:

        Your opinion is valid. But you dont seem interested in listening to Woc and queer peoples opinions if you outright dismiss such opinions purely on the bases of “ Harry would never date someone problematic”. And btw prior to Olivia he dated Camilla Rowe who literally made racist posts and mocked gay weddings.

    • Songs (Or it didnt happen) says:

      If a male celebrity dumped his longtime partner and the mother of his children and was “suddenly” dating a much younger actress that he had just directed in a movie, he would be getting dragged left, right and center. Especially if there were stories about taking their relationship slow and her spending time getting to know his children. It ain’t cute when men do it, but because it’s Olivia Wilde and Harry Styles, everyone gives her a pass and goes YASS QUEEN, GET IT!

      • Merricat says:

        I don’t think that’s true, at least not for me. I think someone who has ended a relationship has a right to do that; why would you want someone to stay if he or she wants to go? People change, some people grow in different directions. What I don’t like is people who stay in relationships while constantly cheating. What’s the point of that?

      • SM says:

        I agree her leaving the relationship with kids for a younger jump off of whom shebis the boss, does not sit well. If it were male, we would indeed be dragging him left and right here. I also get a needy vibe from her. She wants to appear so artsy (if that Don’t worry darling that is circulating on youtube is indeed official, it is eye roll enducing), very woke and very much desired, hence those leaks about how Jasom Sudeikis can’t get over her and the teenidol Harry – enough of her. A bit too much, that’s all.

    • Aud says:

      I think it has to do with how she treats her exes. Like saying her vagina was dying or something when she was with her ex. That’s just mean. And then likely cheating with Harry.

      • BothSidesNow says:

        @ Aud, that’s the reason I dislike her. She trashed Sudeikis in her interviews and played wack-a-mole with her timeline as to when she started sharing pillow talk with Styles. I give her the stink eye due to her manipulating the timeline and her trying to cover up the fact that she was probably cheating on Sudeikis with Styles. Her character is certainly not one that I would consider kind or compassionate. As for who she is f’ing, I could care less. And how convenient for Styles for her to be making all of the concessions into making their relationship work.

      • Cava 24 says:

        Re: trashing Sudeikis – she was clever about it but her comments in Vogue about being “the happiest she’s ever been” and linking that to people she has in her life now, having made changes (which was very “we are obviously talking about Harry Styles but I am being coy”) were Ben Affleck-adjacent. If Ben Affleck had said that, or Chris Pratt had said that, people would not be giving them a pass. They would be like “wow, you are a d*ck”.

    • Merricat says:

      Lol, so many people who want to tear her down for all sins, real and imagined. And put my opinion on trial because of it. Okay, that’s your business. I’m sure you have your reasons.
      I tend to look at life analytically, because I find that often, emotion obscures reason. A relationship ended, another began. Just another day in the life.

    • JJ says:

      Agree with you, I like her. But then I guess I don’t have the insight into her PR intentions that ppl seem to have.

    • Mrs.Krabapple says:

      I don’t have real animosity towards her, but I have mild dislike. For me, it goes back to when she was married to that Italian dude. She made a point during an interview of talking about him being a PRINCE, but don’t worry because she’s still humble. But Italy does not recognize any of those titles, and hasn’t since before the guy was born. (*I* am as much an Italian prince as he is). PLUS, even if they did still recognize them, (which they don’t), titles did not pass to illegitimate anyway, so he would have NEVER been a prince. But she brought it up anyway, which seemed (to me) pretentious and humble-bragging.

    • Sudie says:

      I don’t know but I get desperate vibes from her since she’s been with Harry. I think she is a woman who met a much younger man and fell madly in love with him and is so desperate to hang on to him that she will literally do anything to keep him happy & supported. Some part of her life has to suffer and unfortunately, I think it has been her relationship/time spent with the kids. And please don’t say I’m a Harry fan, because nothing could be further from the truth.
      People mag has been known to plant stories like this for one party or the other when a break-up is imminent, guess time will tell.

  3. Stephanie says:

    Until last month, he Was on tour. And recently he was back in London filming scenes for My Policeman. Which I guess is the basis of the people magazine article. It’s the life of loving of musician. I just think it’s smart to slowly introduce your kids. My friends with kids, some of them have taken several months before their new partners have met their children.

  4. Sinead says:

    I’ve been a fan of Olivia’s since she was in House but I don’t remember ever reading much about her personal life, yet since she’s been with Harry we’re hearing regular updates… it’s weird that Olivia or Harry would be releasing info about their relationship (neither have been like that before) yet here we are!

    • Tiffany :) says:

      Just because a tabloid prints an article about a relationship, it doesn’t mean anyone spoke to them. 80% of tabloid content is speculation and conjecture told as if it was fact.

      • Stephanie says:

        There really isn’t anything new in that article at all.

      • milliemollie says:

        When People Magazine writes something then someone from that celeb’s circle talked to them. In most cases it’s the publicist who provided the quotes.

      • Jules says:

        Not true. Where did you get this 80% stat from? People, US mag and ET all quote from “sources”, which are straight from the publicist. Online gossipy sites can use reader sightings or anonymous reports- that is not speculation though. Generally, where there is smoke, there is fire.

      • Tiffany :) says:

        My understanding comes from my experience.

        The phrase “Sources” can be used when there is no source…just assumptions based on what is public knowledge. Everyone knows they have been together for almost a year, so “they’re making it work” is an obvious un-risky headline to run with.

        Sometimes publicists do work with tabloids, but frequently they don’t. In the US the liable laws protect you if you say something and don’t actually know if it is true or not.

        “Where there is smoke there is fire” is not true when it comes this kind of thing. They publish content that is 100% made up ALL THE TIME. Again, I know this from experience. It’s a phrase that is used to justify belief in a source that has no credibility.

      • milliemollie says:

        First it was 80%, now it’s 100%…

      • Jules says:

        @milliemollie lol, now this sounds like an expert source.

      • Tiffany :) says:

        Millie needs work on reading comprehension! I didn’t say that 100% of stories were made up, I wrote that stories that are entirely fiction are printed all the time. Try to keep up, dear.

        And yes, I do know the truth behind situations and I can compare them to what is printed, so I do have actual knowledge about this system. Go ahead and believe whatever it is you think you are reading. Must be challenging for you.

      • milliemollie says:

        I know how you meant it.
        You’re throwing in percentages to make your claims look legit, Tiff.
        This update came directly from Olivia’s team, We all know here how celebs and People Magazine work together. People does not need to make anything up, they’re not Intouch or OK Magazine.
        Happy Holidays and try to be less condescending next year, dear!

      • Tiffany :) says:

        If you knew how I meant it, you wouldn’t have written what you wrote. I know my claims are legit because it’s been my lived experience for over a decade. When you say “This update came directly from Olivia’s team”, you are trying to sound certain when really you don’t know. You are doing exactly what tabloids do, sounding certain when they are only speculating.

        So while you might not grasp how false information travels, you are showing an example of how it is done.

      • milliemollie says:

        I don’t know that for certain. Yes, that’s true.
        You literally wrote that 80% of tabloid stories are speculation. Where’s the study that came to that conclusion? You’re speculating as well.
        Let’s agree to disagree. We’ll never agree.
        I can’t proof 100% these quotes are real and you can’t proof 100% that the quotes are fake.

      • Tiffany :) says:

        Offering an opinion based on years of life experience is different than making a guess based on what you’ve read online (and then presenting that guess with certainty). I’m sorry, but our positions don’t have the same value. I’m fine with agreeing to disagree.

    • Scout says:

      It’s interesting how much more high profile her love life has become now that she is dating the talent in her movie that is about to be released.

      Let’s see how this relationship does after the movie leaves the theaters and the financial incentive isn’t so strong.

      Reading between the lines……it doesn’t sound like they will last.

  5. BlueSky says:

    This story seems random as if she is trying to get ahead of something. I don’t know why we would need an update.

  6. Mia4s says:

    Uh-oh, not the People magazine “They have such a great relationship!” story. They’re doomed. Couple of months, tops. 😂

  7. girl_ninja says:

    I have dated 10 years older than me an 7 years younger than me. It all depends on the connection with the person. Those relationships with those men didn’t work out but I’m not willing to allow age limits to dictate who I date. I think what people were freaking out about is the fact that Olivia is a mother of two with a partner. People concern troll over how this will affect the children. We don’t know what her relationship with Jason was, it may have been falling apart and meeting Harry put the nail in the coffin.

    I DO hope that all the effort is being made on her end to make this relationship work…because it won’t if that’s the case.

  8. Hyperbolme says:

    Well of course she is – she has to justify blowing up her life for this guy.

  9. Concern Fae says:

    If he’s in tour, it’s natural that she’d be the one flying to see him. The test will be when he’s got some down time and she’s working.

    Trying to keep things 50/50 when people’s schedules are incredibly variable is a fool’s game. You do the work and make up for it later.

    • ItReallyIsYouNotMe says:

      I hope it isn’t just convenience for styles and he puts in effort too. it may actually be easier than we think for her to join him when the kids are with their dad. Celebs jump on planes all the time, it isn’t the big logistical nightmare like for the rest of us. She may enjoy jetting off for a getaway in new places when she doesn’t have childcare or work responsibilities. At least I hope that’s what’s happening here.

  10. Lena says:

    Yeah this “source” stuff is always suspect. I only really believe if people who are speaking about a couple go on the record. Otherwise I think sources are just gossips like us, and it’s what they think is true. Like I’m sure it’s been pretty slow getting to know her kids considering their touring and filming work schedules and Jason has them half the time, even though it’s been a year.

  11. Cava 24 says:

    I would be surprised if either of them does a lot of traveling for the next few weeks 😬. She is in pre-production for another film, he supposedly has an album coming in the spring (maybe, Sony hasn’t officially announced it). It may not be that practical to be in the same place at present.

  12. KC says:

    I mean I liked her character in House but I do not get the big deal over her. She has big/distinctive eyes? Maybe that’s what the fellas are into? I really haven’t paid her that much attention but it always seems her relationships ended messily. I get that her ex was caught off-guard and smitten so still having a hard time but she seems kinda normal-ish to me-no big deal. I never really get what guys go for though. Maybe she does special tricks?🤷🏽‍♀️

  13. Basi says:

    Celebitchy friends….we, as “advanced” celebrity gossip followers, agree that this relationship is for PR right??

    • Stephanie says:

      Pr for what? I hope you don’t mean a movie that is not coming out until late 2022?

      • milliemollie says:

        Some fans (of Harry) seem to be in denial.

      • Eleanor says:

        I think it’s PR mostly to revamp Olivia’s personal celebrity and put her back in the public eye. She hasn’t had a big acting gig in awhile and she’s not really known for directing yet. For Styles, it was probably a big loss for him to not be able to tour his last album. This is a relatively low maintenance gig for him that keeps his name in the public eye until he can release new music / fully tour globally again. It definitely helps to promote the movie too, and probably the movie was not originally intended to be pushed back so late.

    • Truthiness says:

      One of the Real Houseflies of NY said that Harry is a fan and that he hooked up with the late night show host everybody loves to hate. So it could be PR to backtrack and cancel out those whispers. I think Harry usually keeps his private life quiet so this is a weirdly placed item.

  14. Jenny says:

    Uh. He’s cute. She’s been posting some really sexy snaps recently. The Dolly Parton costume bugged me.. smacked of body shaming but maybe I’m just sensitive.

    other than that – enjoy life!

    • Market Street Minifig says:

      The Dolly Parton costume bugged me too. Surprising that a feminist would reduce an icon like Dolly to a pair of boobs.

  15. LeonsMomma says:

    I am a fan of her acting and the movies she has directed, BUT she trashes her exes and is a performative feminist, and that always makes me pause about her. She is kind of stuck with Harry because there is no way she can trash talk him after they break up like she did with her first husband and then Jason. Harry’s fans, who already dislike her, will cut her down, and then some. (BTW: The age difference between the two means nothing to me.)

  16. Bobbie says:

    He doesn’t have to do his half of the labor in the relationship. He’s famous. He’s in his 20s. At the height of his handsomeness. The women are lined up, I’m sure.

    • Mcmmom says:

      Yeah, I tend to agree. I can’t imagine many men in their 20s putting in the emotional work for a balanced relationship with an older woman with kids – which is why as talented and engaging as Harry Styles appears to be, you couldn’t pay me to be in a relationship with him (plus the fact that he’s way too young for me). It seems that he’s probably very happy if a woman wants to go along for the ride (which she seems to), but he’s not presenting any false scenarios. He’s who he is and she is welcome to Join him – or not.

      I don’t have a strong opinion about her, other than her comments about her ex husband (before Jason) were tacky. People fall out of love all of the time and I don’t judge her for ending it – but why kick the dead body by saying such disrespectful things about your marriage? Tell your best friends that the physical attraction was gone, but keep it out of the press.

      • Bobbie says:

        I can’t see him wanting to do it if he was in his 40s. Famous, women lined up. There’s no incentive.

  17. washappy21 says:

    I don’t for one second think he’s 100% into her. Yeah he’s having fun but I just don’t see this being totally exclusive and all that long lasting. Maybe he hasn’t been papped with anyone else but I just don’t get the feel that he’s all in.

  18. Tw says:

    She’s pregnant It’s why they are emphasizing that it’s been a year and her kids know him.

    • Cava 24 says:

      Hmmmm. I am not sure her messaging that she is doing whatever it takes in the relationship is really the ideal way to start seeding that. And I think she likes having clear boundaries around when she is responsible for childcare. She made a few comments about women being expected to drop their careers to do childcare during Covid (one was in the Hollywood Reporter) and Jason said on a podcast that he thought Covid played a big part in their breakup (this was after the breakup but before she went public with Harry), I sort of took that to mean they didn’t reach a balance with domestic obligations. Seems like jumping right back into a new set of obligations might be unappealing, even if Harry is very cute.

  19. Isabella says:

    To be fair, you can’t be under the radar when you’re dating Harry Styles. Taylor Swift sure wasn’t. Seems like people are uncomfortable about the age difference between a woman and a man when the guy is famous (Priyanka and Nick). Otherwise, they hardly notice.

    And, of course, men in Hollywood hardly ever date women their own ages.

  20. Market Street Minifig says:

    “I hope Harry flies to see her too, and that he’s expending some time, emotional labor and effort to make this relationship work. Because that’s not the impression I get at all”

    Maybe the reason you get that impression is because he hasn’t said one word about her to the press. He’s a private guy but I’m not going to get carried away listening to anonymous sources. It will be interesting to see what happens as they get closer to releasing their movie.

  21. LynneF says:

    I’m wondering if Olivia is trying to re-live her 20’s with Harry that she missed by marrying so young? It seems she is enjoying herself joining him on tour all over the country.

  22. Likeyoucare says:

    Is this story came from her PR person?
    If it is, then i felt sorry for her. Harry haven’t said a thing about her.
    The way i saw this,
    Olivia: look at me i’m dating harry style.
    Harry style : Who?

    • Jayna says:

      Harry doesn’t really talk about his relationships in interviews, but he wrote about his last girlfriend, Camille Rowe, in some songs on his album Fine Line, about loving her, about their breakup. She left him for someone else eventually, an art gallery owner. He cheated on her before from lyrics he wrote in one song. I expect that’s what we’ll see in his next album regarding Olivia, some personal lyrics about being with her.

  23. Anne says:

    I was just reading about her and I was surprised that she is only 37, I thought she is in her mid-forties at least. Just to clarify, I am not offending mid-forties ladies here, of course, I would never, I am just stating that she in fact seems significantly older than her age to me, and I don’t even know why. It is some sort of an impression she is leaving.
    Also, it seems like she hasn’t been single since 2003, she is just going from one relationship to another, which is always a huge red flag for me.

  24. MsGnomer says:

    Comment above regarding animosity is right. I see entitlement and ambition in her. Not feminism or intersectionality at all. Sorry. feel like her “woman director” label is a PR position that was the best idea someone had at a meeting, so it’s being drilled into the public space. It seems to me that she has a lot of animosity in herself; coming from her background and with her obvious beauty, why does she have to prove herself/stop ignoring me!!
    maybe I am so wrong. If I am, I’m sorry. Good luck, O… Hollywood sucks.

    Reading about the H&O romance, I don’t expect much integrity. As far as their public relationship, she needs him more than he needs her. It’s just so boring. Would rather go with the AC hook up mentioned above. That’s happy gossip. Smooch James Corden again and make him all aflutter. 😂