Olivia and Jason met and started dating in 2011. They got engaged in 2013 but never married. Their first child, Otis, was born in April 2014. Their second child, Daisy, was born in October 2016. They resided in Brooklyn, New York for most of their relationship but bought a house in Silver Lake, LA in August 2019. They seemed to relocate there at some point in early 2020.

KEELEY HAZELL

Jason met Keeley Hazell on the set of Horrible Bosses 2 in 2014.

Ted Lasso was greenlit on October 2019. In season 1 of the show, there were only two main female characters: Keeley Jones and Rebecca Welton. Keeley Hazell's full name is Keeley Rebecca Hazell.

Whether Rebecca Welton's character name is based on Hazell is up to interpretation, but Keeley Jones isn't. Juno Temple, the actress that plays Keeley Jones, said the entire character of Jones was based on Hazell. The premise of this character would've been conceptualized before October 2019, when Jason pitched it to Apple TV. Jason isn't the only writer and producer of Ted Lasso, but Juno specifically said that Keeley was based on "Jason's friend Keeley Hazell."

^{SIDENOTE 1: Olivia and Juno worked together in 2015's Meadowland and Olivia used to follow Juno on Instagram. Here's a like Olivia left on a pic of hers in 2019. Olivia has since unfollowed.}

Aside from being the inspiration behind either one or both of the main female characters of season 1, Hazell was also cast in a small role as "Bex" (short for Rebecca).

^{SIDENOTE 2: Olivia's personal assistant is called Rebecca "Bex" Holstein.}

^{SIDENOTE 3: Olivia, despite being at that point the partner of the main writer and producer and having pushed him to do the project in the first place, only had one name-drop on Ted Lasso. The character was an extra with no lines and just her real last name (Cockburn} on the back of a football jersey. But perhaps she didn't want one.)

Hazell herself seemed to find this amusing as she tweeted and instagrammed this picture and caption (she has since, deleted it from instagram). Saving the screenshot just in case.

Hazell and Jason would start an on-and-off relationship that spanned 2021 and 2022, inviting speculation that Jason cheated on Olivia with Hazell. This was never brought up by the media, only by fans online.

DON'T WORRY, DARLING

Olivia started to conceptualize her sophomore directorial project Don't Worry Darling on July 2019. Olivia said initially she wanted to play the female lead, Alice, but decided not to when she saw Florence Pugh's performance in Midsommar (July 2019). We don't know exactly when, but Shia LaBeouf was picked for the lead male role, and both Florence and Shia, alongside Chris Pine were announced as the main roles for Don't Worry Darling in March 2020.

According to Olivia, Shia was not the first choice to play Jack. That would've been Harry Styles, whom she'd seen in Dunkirk (2017). Harry's schedule made it impossible as Don't Worry Darling was supposed to start production in the spring/summer of 2020, which was when Harry was supposed to tour. COVID would halt both events.

TROUBLE IN JOLIVIA (?) PARADISE

During late 2019 and early 2020 Jason would miss several important dates for Olivia. Of note was The Independent Spirit Awards in February 2020, where Olivia would be awarded Best First Feature for Booksmart. The reason was that he attended the SNL after-party in New York City. Jason was not hosting the show that night. He was just part of the cold open and could've probably made it with no issues, but perhaps she didn't really mind. She hasn't spoken about it. It's all speculation.

The timing of this couple's breakup is one of the main mysteries of this whole saga, so it will be addressed later.

SHIA OR HARRY

I won't dwell a lot on this, because I don't think it's actually that relevant, and I think Shia just wanted to use Olivia's fall from grace for his own redemption (which I refuse to contribute with). Reports say that Shia was combative. He insisted on having rehearsals in person with Florence, who was hesitant because she'd recently lost a friend to COVID. Shia was on the verge of quitting in mid-August, when Olivia sent him a video asking him to please reconsider. In this video Olivia is seen calling Florence "Mis Flo" in a sarcastic tone. People would use this video as their reason for the wedge that would later become evident between Florence and Olivia, but I 100% disagree.

According to Olivia, Shia agreed to stay in the movie after the video and later gave her an ultimatum that involved Florence, essentially making her choose between one or the other. Olivia chose Florence, which meant that Shia exited the project. This means that both Shia and Olivia can confidently claim that he quit/she fired him, without technically lying. Harry Styles would be announced as Shia's replacement on September 11. I can't for the life of me find this anymore, but I remember vividly that Shia was confronted with Olivia's version of events and he said that he "wished her the best with her movie." If anyone can find the quote, I'll appreciate it.

CHEATING OR NOT?

Harry Styles and Olivia Wilde would begin a relationship while filming Don't Worry Darling. When did this relationship start?

Olivia was in LA from February 2020 and on. After spending most of the summer in Europe, Harry would head back to LA to film the movie. He was spotted grabbing dinner with Florence on October 20, and it's believed that at this point pre-production was underway. Florence would say in her instagram stories that filming started on October 26.

Follow me for a second to a tangent that isn't one. On October 31 2021, after spending a week with Harry, Olivia would be spotted carrying a new bag while departing from JFK towards LA. The bag was a customized Bode bag from their senior cord line. Harry was seen wearing corduroy pants belonging to the same line for his 2020 Vogue cover. Essentially, the item is hand-painted with references given by the person that commissions it. The bag seemed to have references to Harry and Olivia's relationship. I don't have them on hand but I remember reading about them in Deuxmoi. If anyone has screenshots of those stories, they'll be appreciated. One of the drawings in Olivia's bag was a plate with a fish and the date "October 25." Considering the date in which Olivia was seen with it for the first time and the date in the bag itself, it's believed by fans and onlookers that this was Harry and Olivia's anniversary (October 25 2020).

Olivia and Jason's breakup was announced by People Magazine on November 13 2020. This article included that the couple had separated at the beginning of 2020, and this claim would stay undisputed for a while.

SHE WAS THERE: The Nanny

The nanny wouldn't come into play until two years later, but we need to introduce her here because this is when the events she narrates took place.

Disclaimer: I think the nanny is telling the truth, just her version of the truth, which is incredibly negative towards Olivia and gives Jason all the leeway in the world. I'll elaborate.

The nanny claims that, while Jason and Olivia did have a big fight at the beginning of 2020, they didn't separate at all. That they were fine and didn't seem to have issues. For a full recap of the nanny, I recommend actually watching her video, which makes a lot more sense than the pulled quotes (she does sound... too involved for a nanny, though).

The nanny points out that Jason and Olivia were spotted together several times in August and September 2020, one of those times was a beach outing in Malibu, where Jason and Olivia can be seen play-fighting. This was on September 10. On September 3, we can spot Jason and Olivia leaving Nobu together as well. The timeline of them breaking up in early 2020 is not adding up. I know there were Gossip Cop articles in February 2020. I've seen the screenshots, but I was actually able to pull the article from the now-defunct site via Web Archive, and it's the very unreliable Life & Style speculating because Jason missed Olivia's award ceremony.

The nanny claims that Olivia kissed Harry at a cast party in October, and then used a COVID scare from set to move to a hotel near the house. She claims Olivia came back on November 8 and dumped Jason, who would later find out about her and Harry through reading text messages between them on her Apple Watch. The nanny also claims that Olivia told Jason that Harry and Florence were sleeping together before he found out about her and Harry, as a way to deflect and not have him suspect anything.

IMPORTANT: This is what I think caused trouble between Florence and Olivia. Florence was dating Zach Braff (who she's still on good terms with). Harry and Zach are/were very close friends. Zach is also friends with Jason and worked on Ted Lasso. If Olivia truly lied about this (and Florence and Zach staying together for another year and still being on good terms suggests it was definitely a lie), then it makes perfect sense for Florence to be upset with her.

The nanny claimed that on November 15 there was an incident in which Olivia was preparing a salad to bring over to Harry's, and Jason got so upset that he followed Olivia through the house while filming her and then laid under her car to prevent her from leaving. This claim sounds absurd, but there are dated screenshots of text exchanges (1 and 2) that corroborate that something happened.

According to the nanny, who doesn't seem to care about Harry in the slightest, Harry was completely unaware about any of this and Olivia repeating that her and Jason's relationship ended in early 2020 was in an effort to convince him and not the audience, not only about the timeline, but also about the involvement that she and Jason reportedly kept having until late 2020.

The caretaker, who DailyMail.com has chosen not to identify, also says Wilde's twisted version of events was an attempt to save face in front of Styles - who the nanny claims 'doesn't know anything about' how she continued seeing Sudeikis and slept naked in the same bed with him even after their November 2020 split.ย?

This, while also sounding ridiculous, seems to be corroborated by the fact that Jason continued to call Olivia "my partner" until... January 4. And this date will be important in a second. Here he calls her "my partner" on November 13. Yvette Nicole Brown moderated a Q&A on January 4 where Jason called Olivia "Olvia Wilde, my partner." That same day, pictures of Olivia and Harry holding hands at his manager's wedding (taken on January 2nd in Santa Barbara) would drop.

Over the course of the following days, multiple sources would claim stuff the nanny claimed later, the Apple Watch claim, that Jason was desperate to get her back, that he didn't know she wanted out of the relationship until it ended, and that Olivia told Harry that she was single.

This also lines up with what Jason himself would say in his GQ interview in July 2021, including that the relationship had ended in November 2020 and that he didn't know why.

All evidence seems to point out to Olivia lying, to both Jason and Harry and cheating on both of them. I'm giving Harry the benefit of the doubt because I struggle to believe that he was okay with her sleeping naked with Jason and telling him she loved him while beginning a relationship with him (Harry), and because he included the October 25 date in the bag, even after Jason said he and Olivia broke things off in November. Bit of a rookie move, right? If not for being a genuine good person, for being perceived as one.

I honestly can't really give Olivia the benefit of the doubt because nothing points to what she claims, but I will say, that I think, considering some of the attitudes we've seen of Jason (lying under her car, scaring her and the nanny, the Cinemacon thing, allegedly litigating her into debt) I can see why Olivia would struggle to leave a toxic relationship. She clearly didn't handle things well, but if a friend of mine was in that situation, would I judge her? Probably not.

It is quite unfair to her kids, to Harry, and to herself, but she doesn't deserve to be burned at the stake for it, in my opinion.

So, I think Harry and Olivia began seeing each other in October and (in his mind only) made it official on October 25, Olivia ended things with Jason on November 8 but continued to give mixed messages, and things finally ended when Jason, the kids, and the nanny went to London to film Season 2 of Ted Lasso (December 29 2020).

To end this long ass segment, here's more screenshots from the nanny, that weren't included in the other articles.

THE MESSINESS

Olivia and Harry continued their relationship, Jason was spotted at Keeley's house in London multiple times. His team would try to deny the relationship or play it off, but they'd be spotted PDAing in New York and Cabo, etc.

Other isolated events were Cinemacon, which I won't rehash because it's a thread on its own, but let's just say that Jason served Olivia papers in front of everyone while she was introducing Don't Worry Darling at Cinemacon in April 2022. The process server had to pay $1,000 to access the event and fill several COVID protocols. People at Cinemacon said there was no way the process server accessed this event by their own volition. Olivia said Jason tried to humiliate her, and I agree with her.

The whole Florence/Olivia and Olivia/Shia thing happened, I already explained my thoughts on both of them. Because of all these messes, Olivia was in the eye of the storm and the subject of criticism on every corner. Fans of Florence, Jason, and of course (and leading the charge), Harry, absolutely despised her. Jason and Shia made things a lot harder for her, and the media decided that piling on was a great idea. I don't claim that the way Olivia handled things was perfect. I think she shouldn't have talked about Shia's departure if it was so convoluted, I think what she did to Florence was objectively wrong, and I think the way she handled leaving Jason/starting a relationship with Harry was not okay, but nothing, absolutely nothing, justifies the pile-on campaign she received. The way this world hates women is revolting.

THE BREAKUP

How and when did Harry and Olivia break up? Are they still on good terms? Are the claims that they were rekindling their relationship true?

Harry has been touring for what seems like years. In the summer/fall of 2022, he did residencies in four cities in America: New York, Austin, Chicago, and LA. New York and Austin went without a hitch, but when it came to Chicago, the first concert was postponed due to "band/crew illness" from October 6 to October 10. His two main musicians were spotted out and about Chicago that same day seemingly completely healthy, other members of his band were posting on social media looking healthy as well. Sony, Harry's record label, issued a statement saying that Harry wasn't sick. Also, what kind of illness would affect enough people to postpone an entire concert but only for two days (his first concert would be the 8th)? He had performed with one or more members of the band missing and/or with replacements before, as recently as during the NYC residency. It left everyone scratching their heads as to why Harry had postponed this concert, which was something he'd never done before.

Olivia was spotted by fans of Harry's at the Chicago airport the next day (it was a Friday which might be important). She was then spotted at Harry's first Chicago concert on October 8, but she wasn't present at the second one on October 9 and was seen in LA the next day.

Harry's third Chicago concert was on October 10, then he had two days off, then his fourth concert on October 13. His mom and sister would fly all the way from England to watch this show (presumably after spending his two days off with him), then went back to England the next day. This was extremely odd, as they usually only travel to see him in big cities in America and stay a week or two or attend his shows in London/Manchester. People speculated that it was because of Harry's mom's birthday, but that wouldn't be until about two weeks later.

Harry continued with his last two concerts in Chicago on October 14 and 15, and when everyone expected him to go back to Olivia in LA, he stayed back in Chicago an extra day, golfing. For the past couple of months, for the first time in their almost 2 year long relationship, they'd been forced to spend a lot of time apart because Ted Lasso had extended filming in London and the kids had school in LA, which meant Olivia had to stay with them the entire time and couldn't fly to Harry every other week like she used to do. So why did he prioritize golfing in that context?

Harry went off the grid for the next two days (October 17 and 18) but was rumored to be in the East Coast, while Olivia was in the West Coast with her kids.

October 17 and 18 would also be the days where the nanny articles would drop. I linked them above. It's incredibly unlikely Daily Mail would publish such a piece without reaching the parties involved for comment before, and I presume the reaching out happened... on October 6.

I think Harry was told by either his team or Olivia herself about the articles and its contents, and I think it upset him enough that he couldn't perform. I think he either ended things with Olivia right there or threatened to, which made Olivia drop the kids off with a friend or a nanny for the weekend (remember she traveled on a Friday evening to Chicago?) and try to fix the relationship. I think it didn't work out and they broke up. I think Olivia stayed for the concert for optics, since she was spotted at the airport by fans, but left immediately after. I think Harry was not in a good state and his mom and sister had to fly in to comfort him. And I think that after that, Harry and Olivia were 100% done and there was absolutely no way they'd ever get back together.

The breakup was announced on November 18, but between October 6 and that date, Harry and Olivia were only spotted together twice. Once on October 19, and the pictures look like Olivia is trying her best not to look affected and Harry isn't trying at all. The second time, on October 25, their supposed anniversary, grabbing very casual (I'm talking about the way they're dressed) lunch on a car.

During this time, Olivia and Harry would attend the same gym the same day but at coming and leaving when the other one wasn't around multiple times. Olivia went to a few concerts of Harry's during his LA residency and was spotted at the last one on November 15. People would announce the breakup on November 18, calling it "a break" and claiming they were "staying friends."

In my opinion, the October 19 date, the time between the real breakup and the announcement, and the wording of the announcement, were meant to try and save Olivia from even more backlash. I think the fact that DWD was still in theaters when they broke up made the decision to keep the breakup under wraps even stronger, as well as Harry's LA residency, which is where Olivia was living. I think the October 25 lunch was organic and was probably just recent exes grabbing lunch for closure.

I don't think there was a dialogue after the breakup other than maybe some cordial hi and bye, and I don't think there was ever the slightest possibility that they'd get back together.

THROUPLE?

There's a lot to address here and most of it is BS. First of all, Deuxmoi published claims that Harry Olivia and Emily had a threesome, then said it wasn't true and it was an "urban legend" (I don't have screenshots, send them my way if you have them).

BETRAYAL

Second of all, Emily and Olivia's "friendship" which wasn't a friendship at all. Olivia didn't follow Emily on Instagram until July 2022. You can see in this screenshot that Emily comes several people after Mitch Rowland, who's Harry's guitarist, and she followed Mitch on June 16 2022. People claimed that Emily was Olivia's guest at Harry's show in Paris (July 5 2022), but it turns out, Emily had a Balenciaga show in Paris the next day. Lenny Kravitz was also at the same Paris show. Celebrities don't need to be invited by anyone to attend big shows. They can just ask their agents for tickets.

Aside from standing next to each other at Harry's concert, the connection between Emily and Olivia was that Emily talked about the sexism Olivia faced in an interview in November 2022, that they were at the same Vanity Fair Oscars after-party, and that they follow each other on instagram. That's it. That is not a friendship. It does not make Harry (or any of Olivia's exes) "off-limits", and it does not constitute a betrayal.

This is another case of the media going straight for misogyny to keep a story alive.

HOW DID HEMILY (?) BEGIN?

That is a great question with no specific answer. Harry followed Emily on Instagram on November 15, but Emily had been following him since late 2020, you can see Harry here is several people below Romy Glow, who was the makeup artist that did Emily on her Vogue cover October 26 2020. They both followed each other on twitter in the 2010s (I don't have a source for this, but seeing the amount of stuff I could find on fan pages, the fact that they both follow each other but I can't find dates means it was likely before fans were paying attention to follows like that).

Emily attended the Met Gala Harry co-chaired in 2019, and they both attended the Gucci after-party. Harry then hosted his own after-after-party with Kendall Jenner, and while Emily was not mentioned as one of the attendees, she wasn't mentioned as attending any of the other parties, and her usual posse (Bella Hadid, Hailey Bieber, Rosalia, and Kendall herself) were at Harry's after-party, so it's very likely she attended as well.

I wouldn't say that they were friends, but they clearly knew each other. It's possible that they started communicating after Harry followed her on Instagram (though, around that time, Emily was dating multiple men at the same time, goodforher.gif). Nothing indicates that they were ever around each other until Tokyo, so whatever happened couldn't have possibly started in person until Tokyo.

WAS IT A ONE TIME THING?

In short? I don't think so.

I think Emily went to Tokyo because Harry flew her in. Emily was last spotted in NYC on March 18. Harry had a concert in Seoul on March 20, and reportedly got to Tokyo on March 21, where he would have two concerts, one on March 24 and one on March 25.

Harry has been very vocal about loving Tokyo for years. He has a bunch of friends there and always stays a bit extra. The second Tokyo show would be the last one in his Asian leg of tour and he'd have a two-month break afterwards.

Emily was able to move around Tokyo without being spotted the entire time she was there. She posted a ton of pictures and videos from her trip on March 30. It's likely she got there before his concerts and even attended them. Why do I think that? Because she followed one of Harry's friends on instagram when she got back to NYC. The friend had followed her first. Her name is Holarena. This woman has been Harry's friend since he was in One Direction and seems to be a translator for Live Nation (his concert promoter). There is virtually no reason for Holarena and Emily to know or follow each other aside from Harry.

Emily's Tokyo trip was with two of her closest friends, both went off the grid when Emily did (a few days before the kissing videos) and surfaced at the same time (March 30). Also during this trip, one of her friends followed Harry's BFF and producer Tom Hull (also known as Kid Harpoon), who was in Tokyo with Harry.

^{SIDENOTE: I'm not linking any of these friends because it feels weird.}

Emily has not cited a reason to go to Tokyo. She didn't post about work at all, only about comping her hotel. What are the chances that her exact week in Tokyo matches Harry's and that they're spotted making out and that there's follows going around that link his and her group together?

Deuxmoi claimed that Harry and Emily both attended the HVN party hosted by Kiko the 25th and that the kiss was a random drunk hookup because they were at the party, but nobody posted about either of them being at the party despite a ton of social media posts going around. Emily and Harry both have a good relationship with Marc Jacobs. If they were to go to one of his parties, wouldn't that be promoted? Especially Emily?

The Sun claims that Emily definitely wasn't at the party. The kiss happened in the middle of a street party, not at the club. It's entirely possible that Harry and Emily went out on their own (with their friends, but not to the HVN party) and that Harry picked Kiko up after hers was finished to walk her home since her boyfriend seems to be in Australia, as in "we're both out and about and I don't want a woman to walk home alone drunk." Emily had her friends with her, and it's also possible Harry walked her home first, since we didn't see them leave the street party.

As per going home together to sleep together. Well, they had a week to do that. It doesn't have to be at night and it doesn't have to be after going out. It could also be that they're taking things slow. Or that Emily didn't want to get home that late or bring back a man (she had her son with her for the trip). Not being seen together immediately after the kiss doesn't mean that things started and ended there.

IS IT SERIOUS?

Nah, I don't think so. I think they're having fun. It's unlikely it'll ever become serious too. I wouldn't be surprised if we never saw them together again. I also wouldn't be surprised if we did. I think it just depends on how much they enjoyed their time together and what they want to do next and when. There's no way of knowing.

WAS IT FOR PR?

No way, in my opinion. For a lot of reasons, but mostly because of what Lainey Gossip said:

Some people are calling this a PR stunt. Hereโ€™s why I donโ€™t think itโ€™s a PR stunt. First of allโ€ฆ why? What could Harry possibly need the PR for? And why would he agree to go along with whatever PR you think Emily is after? Second, and more convincingly, the reason I donโ€™t think itโ€™s PR is because, well, if it was PR, Iโ€™m not sure Harry would want to be seen as such a bad kisser? I mean, this is giving first kiss during Spin the Bottle, not international heartthrob. If he staged this kiss, youโ€™d think heโ€™d serve more lip swag. As you can see, Emily is trying to bring the technique, but heโ€™s not giving her much to work with, LOL.ย?

I think them being intoxicated (particularly Harry who still had trouble walking in a straight line hours later) and feeling confident about not being spotted in Tokyo made them be a little careless. It definitely looks like they spot the camera once or twice, but it could easily be glancing in the direction of it while not actually seeing it. I just can't imagine what Harry could possibly gain from this. He's already over-exposed (and he knows it). He doesn't have music, movies, or tickets to sell, so it seems pretty pointless.

There's also the fact that the media is scrambling to find an angle and doesn't seem to know where to start. Usually with set ups, there already is one, and it's fed by the team/s of the celeb/s involved. The whole thing seems completely aimless.

SOURCE(RER)S (STONE)

And lastly, the amount of sources that point to completely different directions are infinitely amusing. You have US Weekly saying Harry is thrilled about the hookup. Page Six saying Emily is begging for forgiveness. The Sun going for the angle of calling Kiko "Harry's former flame" even though Kiko denied it twice years ago and she has a boyfriend (the second time wasn't picked up and she denied it in Japanese on Twitter, and her profile is now deleted, but Bobby Berk told the whole story of what happened). And People Magazine saying Harry and Emily are friendly and Emily wants to continue seeing him (People tends to be the closest to celeb teams).

Personally, I think the begging story is absolute BS. I don't know that any team pitched it, but if I had to choose one, I'd go with Olivia's. Not because she actually feels betrayed or want/ed Harry back, but because it would serve to bury the mess about her net worth statements leaking, which her rep called "an utmost breach of trust" right before the kiss (March 24, the kiss was March 25). Even then, it could just be Page Six being messy for the sake of it.

Emily liked Harry's instagram picture, posted right after the "begging" story, and I believe her team planted the "she wants to keep seeing Harry" source in People, at least partly to counter the Page Six narrative.

I'm sure Harry is thrilled about whatever happened (not so much about the whole world finding out), but it's extremely unlikely anyone close to him is speaking.

^{(I think})

I need to thank the fellas who helped me source the fan stuff from here. I've been asking around for a few days to put everything together. If it wasn't for those accounts and the little tips I was given, I wouldn't have been able to pull off like, half of this, so thanks!