Olivia Wilde & Harry Styles’ friendship ‘quickly turned romantic’ on the set

Olivia Wilde attends the Vanity Fair Oscar Party at Wallis Annenberg Center for the Performing Arts...

Personally, I don’t like Olivia Wilde that much, but she’s not on my permanent hate list or anything. I just find her annoying and pretentious, but sometimes she’ll do, say or wear something that I find interesting. And I’m pretty interested in her new romance with Harry Styles. I find them an odd couple, not because of their ages (she’s a decade older than him) but more because of the fact that they’re in such different places in their lives. She’s a mother of two getting out of her second long-term relationship (which was a lot like a marriage) and she’s made major moves to be taken seriously as a director, writer and producer in addition to her acting career. And Harry has been around the music industry for years, but he’s really just “starting out” in a lot of ways. I don’t know. Maybe it will be fine.

Olivia and Harry met on the set of Don’t Worry Darling, which will be Olivia’s second feature length directorial effort. She also co-stars in it, along with Chris Pine, Florence Pugh, Gemma Chan and others. Shia LaBeouf was cast in the film initially, then Olivia fired him and recast the role with Harry. Apparently, sparks flew between Olivia and Harry immediately:

Harry Styles and Olivia Wilde’s new romance might have come as a shock to fans, but those on the set of their upcoming film, Don’t Worry Darling, weren’t surprised by the news. In this week’s issue of PEOPLE, on newsstands Friday, sources says the actress-director, 36, struck up a close friendship with the singer, 26, last fall as they began work on her highly-anticipated sophomore directorial project, which she also stars in.

“What started out as a close friendship, quickly turned romantic,” the source says. “Everyone saw it coming. During breaks, he’s hasn’t been able to stay away and visited her trailer.”

As they spent time together on-and off-set, their friendship “quickly turned romantic,” says an insider. “Their chemistry was very obvious.”

Wilde — who split from fiancé Jason Sudeikis, 45, in early 2020 — brought on the former One Direction singer as the film’s male lead in September. He plays the husband of Florence Pugh’s character, a 1950s housewife who discovers a disturbing truth while living in an isolated community in California. “I did a little victory dance when we heard that we officially had Harry in the film,” Wilde told Vogue for its December issue.

After conservative commentator Candace Owens slammed Styles in November for wearing a dress on the magazine’s cover, Wilde was among many who jumped to his defense, calling Owens “pathetic” on Twitter.

“Olivia was going on and on about how wearing a dress still makes Harry masculine,” says the insider. “It was again just so obvious she had fallen for him.”

Despite their budding romance, the two continue to keep things “very professional” at work.

“Olivia and Harry created this loving and warm environment,” says the insider. “Everyone loved working with them. She takes her work very seriously, but everyone saw it coming.”

[From People Magazine]

Yeah, I get that we’re supposed to think this is cute and cool, but the age gap alongside the professional power gap kind of bugs me, just as it’s bugged me when the genders are reversed and an older male director is smitten with a young actress he’s directing (see also: Darren Aronofsky and Jennifer Lawrence). Everybody has to be really f–king careful. But again, they’re both adults and as long as everyone behaves professionally on the set, so be it and I’m happy for them. Olivia must be so pleased that her second film is getting so much attention already and they haven’t even wrapped.

Kristen Stewart meets friends for lunch at Kismet restaurant in Los Feliz

Harry Styles and Olivia Wilde are dating! Couple is seen on set of "Don't Worry Darling" in early November **FILE PHOTOS**

Photos courtesy of Backgrid and Avalon Red.

You can follow any responses to this entry through the RSS 2.0 feed.

41 Responses to “Olivia Wilde & Harry Styles’ friendship ‘quickly turned romantic’ on the set”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. Bibliomommy96 says:

    I have to admit the age & power gap makes me uncomfortable too. And the fact that they’re still filming. But don’t get me wrong, if Harry was trying to get at me, I wouldn’t hesitate, lol, he seems like a very giving partner,

  2. LP says:

    I mean, 10 years is more reasonable than Jennifer Lawrence/Darren Aronofsky….maybe they’re almost done filming or just wrapped his part and that’s why they’re being more open?

    • AB says:


      The comparison with Lawrence/Aronofsky is spurious. Lawrence was 25 to her director/employer’s 47 years when they got together.

      Internalised misogyny is so deeply entrenched that a man who is ten years younger than his girlfriend is compared to a woman who was TWENTY-TWO years younger than her “boy”friend.

      Does anyone even notice if a man is ten years older than his girlfriend?

      • LG says:

        Exactly!! No one is calling out that Sudeikis is 9 years Olivia’s senior and no one had a problem there…the disconnect here is astoundingly obvious.

  3. Zen says:

    A part of me thinks what great publicity this relationship is for the film. That benefits Harry who is just beginning his acting career and Olivia who is expanding into directing. It could be a real relationship but I can’t help thinking its just so convenient.
    I think this because I’ve never seen such publicity around who Harry dated before. In fact none. I’ve never seen him with a woman before. For Olivia coming out of a long relationship, this is beneficial to show her as a woman attractive and desirable, something that helps her career and self esteem. Win-win for both of them.

    • Reddish says:

      Yes, the rollout of this relationship has definitely been bizarre. Harry is really never this public about his dating life, and I can’t help but think they’re trying to get ahead of the very true narrative that Olivia cheated on Jason with Harry.

      I find the pictures of them together baffling because they all look like stills from a teen movie. There’s one where she’s sitting in his lap in a convertible and the people in the backseat are standing up, while the car is in motion. Or where they aren’t wearing masks in a parking lot with a bunch of people in LA. The rollout is sloppy and cringey, and honestly not a good look for either. They better hope they’re still together when the movie comes out bc that’s all people will want to know.

      I don’t care for either but this is just all around a bad look.

      • Original Penguin says:

        Harry had a very publicised relationship with Caroline Flack- who was also a bit older than him. This doesn’t seem to be outside his ballpark.

      • Cava24 says:

        I don’t think she cheated on Sudeikis but I think they announced the separation because she was dating Harry and they knew someone would get the information out eventually. I do wonder if the timing is related to the fact that a bunch of people were questioning her for casting Shia LeBoeuf in the film (he was fired for being difficult before filming even started and was replaced by Harry) in the first place- it was known that he was verbally abusive to his exes before that and it isn’t exactly on brand for her to hire someone with that history.

        But, yeah, this totally looks like a rollout. People have been noticing all the accessory swapping -sunglasses, his necklaces on her; the terrible Gucci dress hookup her got her (that dress looked like it would have been in a final sale bin at Free People anytime in the last 30 years and Gucci might not have lent it to her for a “private” event where it would not be in widely circulated photos) and her call out of his most recent video with the sweater.

        I still like them and like them together but some of this is cringe-worthy

    • Angel says:

      A part of me thinks that this is nothing but PR for the movie lol.

    • Stephanie says:

      You missed him with Taylor and Kendall, then. There were also a few pap pictures of Camille. Harry can’t win, when he’s lowkey, it means the relationship is meaningless, look at his relationship with Camille. When he steps out, it’s only for pr. Can’t he just date?

      • Sof says:

        I had forgotten about him and Taylor!
        And no, it seems Harry can’t date, every woman he chose had something wrong apparently. I don’t listen to his music but love his song Cherry. It was surprising to read lots of comments trying to diminish his relationship with Camille, she obviously was very special to him, it says so in the lyrics.

  4. mar says:

    I love this pairing

    • anna says:

      me too.

    • minx says:

      Yeah, it’s their business, go for it.

    • Normades says:

      Me too. Harry is 26 and a huge star in his own right. He’s more famous than she is. I don’t see a power imbalance at all.

      10 years when both parties are over 25 doesn’t bother me at all. Plus she’s newly divorced and can have her fun. I bet it’s hot. Get it girl.

  5. Esmom says:

    In that shot from the film, Harry look so much like her ex Jason. That’s all I got. I think they’re fine. Normally I’d be skeptical of a 26 year old hooking up with someone with two kids, as Kaiser pointed out, but Harry seems a lot different than the average 26 year old. At least that’s my admittedly uniformed observation, lol.

  6. Ariel says:

    The bottom picture: PULL YOUR MASK UP OVER YOUR NOSE!!!!

  7. Lillian says:

    I don’t get the whole PR for the film angle. More people aren’t going to see the film cause they are dating, Harry’s fans will see the film anyway. PR relationships don’t do anyone any favours and everyone always comes away from it looking foolish. So not buying it. I do buy her dumping Jason for Harry though. NotSkinnyNotFat on Instagram says she knows for a fact Olivia dumped Jason for Harry and she’s adamant about but won’t say who her source is

    • Laura says:

      I don’t know. I barely heard about this film before, and now I’ve read it’s name 3 times in the last few days. It’s a promotional strategy that’s probably working on me lol

    • Samira says:

      Same with the post above me. Heard about the film from the Shia stuff, but it’s definitely on my radar now that it’s gossip fodder. And I know nothing about upcoming films.

  8. Wiglet Watcher says:

    That black lace on Harry… he has worn better.

    Ok, so older director ending a relationship with partner they share 2 young kids with jumps into romance with young star working under them. Remove the genders and it sounds like a sketchy midlife crisis. I wonder if there was overlap…

  9. mynameispearl says:

    I dont really get a power gap here, I mean ok Olivia has some power because shes a director on this, but he is Harry Fucking Styles! He’s stellar like.

  10. Daisy says:

    Harry is closer to his 30s than his 20s, it’s not the same as an 18 year old dating a 30 year old come on now. Also Olivia and Jason seem to be very friendly still for someone to have been “dumped”. I believe they broke up early 2020 like the report said and decided to release the statement when she started seeing Harry to avoid this kind of gossip.
    But if it’s just PR for the movie, I’m fine either way. I need the distraction lmao they’re both very nice and talented people.

  11. Emily says:

    Maybe Jason can get back with January Jones 😝

  12. Lily P says:

    I think I’d be a hell of a lot less suspicious of this relationship if they weren’t both represented by the same PR agency.

    • Carmen says:

      If you mean CAA, which is not a PR agency (Harry’s management Full Stop Management handles his PR and they have nothing to do with Olivia), then that’s really not much of an indication. CAA is humungous, literally half of Hollywood is signed to them.

  13. Honeychurch says:

    Harry Styles tends to hang out with people a lot older than himself – his circle of friends has always been people 5-10 years older than himself – so this doesn’t look all that strange to me.

    Also, I don’t see a power gap. His music career is going stellar, he’s booked and busy, and if it weren’t for the virus he’d be out on a sell-out world tour. It’s not like Olivia Wilde can make or break his future in entertainment.

    If anything, they look well-matched and happy. Good for them both.

  14. outofthecloset says:

    Too bad. I was shipping him and Lizzo.

    • Carmen says:

      Nah, I think Lizzo has way too strong of a personality for this guy. I like Harry and I love Lizzo, but it feels like she would have had all the energy in this relationship and he’d hardly get a word in. Feels like he needs someone a tiny bit more meek, since he seems like such a gentle guy.

  15. Pull the Other One says:

    They called the paps to take several photos of them in different places on the same day and then released a “new” set of photos of them (along with a new story citing “sources”) every day over the past few days. Whether or not this is for PR, the rollout of this relationship was absolutely calculated.

    • Carmen says:

      I think it was a calculated rollout to control the narrative. Makes you wonder if they wanted to create a picture of a cute couple in love, before maybe word gets out that the timelines were messy or Olivia left Jason for Harry.

  16. Rollo says:

    I really think she left Jason for Harry and all this is to make her look like she didn’t cheat. I can’t see him being in it for the long haul, he’s 26 and Harry Styles but who knows.

    • Natters5 says:

      People Magazine just did an article on Jason’s side of the story using his sources and according to him they were very much together till Fall. She started filming the movie in September and by the end of October she wanted out of her engagement with Jason to pursue a relationship with Harry. Jason’s source said that Olivia and Harry have been trying to give a narrative of Jason and Olivia breaking up early in 2020 so it doesn’t look like she cheated on him. He is apparently heartbroken about this and had hope they would get back together. It is clear now she left Jason (a man) for a boy (Harry).

      • Cava24 says:

        Saw that. Somebody didn’t get control of their narrative before they went public. Whoops.

  17. LillyfromLilooet says:

    Given that she is at a point where she is not looking to start a family and she’s already had a long term partnership, this pairing seems entirely likely. Harry is much better off not breaking hearts of women who are looking for a partner, and I think Olivia isn’t looking to set up housekeeping either.

    I think we all know about what that face fondling lunch of love and regret was with Jason a couple of weeks back.

    You can’t beat chemistry.

  18. Hannah says:

    Legit thought your thumbnail pic was a jacked Hillary Duff 😬 OML! White rich people all be morphing into the same person (pls feel free to remove if off colour / inappropriate) I respect my British sense of humour is not everyone’s cup of tea

  19. Anonymous says:

    Harry and Olivia make a gorgeous couple. Wonder if Aniston and Sudekis would work?

  20. Meg says:

    pretentious- yes she is