Jason Sudeikis went to Cabo with Keeley Hazell but he’s still ‘devastated’ over Olivia

Stars of Warner Bros. Television`s TED LASSO Returning From the Emmys to Celebrate at Sunset Tower Hotel

Jason Sudeikis and Olivia Wilde broke up and ended their engagement at some point in 2020. Sources close to Olivia insisted that they were over in the summer or early fall of 2020, and that she was free and clear to fall for Harry Styles on the set of Don’t Worry Darling in the fall of 2020. Jason’s version of events is that he and Olivia split in November 2020 and Harry Styles was the third party and the reason why Olivia left him. Earlier this year, “sources” were going wild, assigning blame all over the place. It’s settled down a lot in the last half of this year, possibly because Jason is dating other people now too. Over the summer, he was seen out with Keeley Hazell, who plays “Bex” in Ted Lasso. Over the Thanksgiving holiday, Jason and Keeley were in Cabo together:

Jason Sudeikis reignited his romance with former glamor model Keeley Hazell “because he feels safe with her,” following the heartbreak of his split with Olivia Wilde, according to sources. Insiders say earlier this year the relationship between the former “Saturday Night Live” star and British model and actress Hazell had been more casual. But after the pair were caught kissing on a beach in Cabos San Lucas, Mexico, earlier this week, an insider says that British former Page Three girl Hazell is hoping to take her relationship with the 46-year-old “Ted Lasso” star to the next level.

The insider said, “Jason was and still is devastated over his split with Olivia; she’s the mother of his kids. But he has known Keeley for a long time, and he feels safe and relaxed with her. They enjoy each other’s company.”

The insider added Sudeikis’ friends were not initially sure how long his relationship with Hazell would last — because he wasn’t looking for anything serious after his split with Wilde — but they are happy he seems happy with Hazell.

“Keeley has really helped him through his split with Olivia,” the source added.

Their friendship goes back a long way: Hazell spent time with Sudeikis on the set of 2014’s “Horrible Bosses 2” where she played Chris Pine’s assistant. But the insiders say, before that, they already knew each other through friends in Los Angeles. The source added, “Jason met Keeley through friends in Los Angeles. But she now lives in London, where of course he films ‘Ted Lasso.’” He is expected to return to the UK in early January to continue filming the show’s third season.

[From Page Six]

I suspect that Jason and his PR wants everyone to know that while Jason and Keeley have been friends for years, they only became romantic over the summer, months after Olivia “left him.” That might even be the truth, who knows. While I think Olivia Wilde is kind of chaotic in relationships, I’m uncomfortable with the “Olivia left Jason for Harry” narrative which Jason seems to be pushing hard. I feel like it was way more complicated than that.

Apple TV+ Ted Lasso Season 2 Premiere

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40 Responses to “Jason Sudeikis went to Cabo with Keeley Hazell but he’s still ‘devastated’ over Olivia”

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  1. Case says:

    Really uncomfy with how Jason continues to play the “devastation” card over how Olivia left him. That very well may be the case but he moved on quickly with Keeley just as Olivia did with Harry, yet seems keen on making Olivia the bad person who abandoned her happy family. I know the guy is beloved because of Ted Lasso but his PR angle throughout their split has felt very off to me.

    • Snazzy says:

      I developed a huge crush on him after watching Ted Lasso – he needs to let this go and stop disappointing me by playing these PR games

      • JJ says:

        Yeah I actually really love both him and Olivia separately, him for Lasso and comedy roles (great Detroiters guest star!), loved her in Her, loved Booksmart, she’s seems really cool — It felt like he overshadowed her for a long time and it’s cool to watch her succeed.

        I just wish this was over. It feels like watching parents fight.

        Side note, I never got the appeal of Harry Styles, maybe because I’m in my late thirties so he always seemed like a teen, but boy this year I get it!

    • Oh_Hey says:

      Ooof. This.
      Olivia and Jason are both divorcees on top of their breakup but it bothers me how everyone is all over her and not the guy who’s ex wife says he used to pick up women in front of her for “research”.
      The story is tired at this point. If he was that heartbroken they wouldn’t have been engaged for a decade with two kids and no wedding. Also it’s been over a year by either timeline and they both have new folks. Basta – at the very least for your kids. Stop talking about it.

    • Jessica says:

      I became even more uncomfortable w/ Jason’s narrative when I found out 1) Jason has known Keeley for 6 years and has always been attracted to her, 2) Jason named two characters in Ted Lasso after her (her full name is Keeley Rebecca Hazell and the two lead women characters in Ted Lasso are named Keeley and Rebecca), 3) Jason based the character named Keeley in the show on inspiration from Keeley Hazell (as confirmed by Juno Temple who plays her), 4) Jason casted Keeley Hazell in the show, and 5) Jason wrote and filmed the show while still with Olivia, and 6) Jason’s ex-wife Kay all but confirmed he was a cheater or at least a player on Twitter a few years ago.

      He already had the great PR from Ted Lasso; he didn’t need to spin this whole narrative and make what was almost certainly a split w/ a lot of nuance and complication look like he was entirely faultless and Olivia entirely to blame. He got caught w/ Keeley in February, just weeks after Olivia was first seen with Harry, but his PR team kept up the narrative that “they were just friends” or “it was totally casual” so he could keep up the “heartbroken victim of cheating and single devoted father of two focusing only on his kids” narrative. But reality is Jason and Keeley have been together for nearly a year now—about the same time as Olivia has been w/ Harry. I wouldn’t be surprised if Jason being emotionally unavailable/detached (b/c of Keeley and/or some other reason) made Olivia feel ready to cut ties. In any case, I think his PR campaign around the split has been pretty slimey.

  2. Enny says:

    Ugh. I want to give this the benefit of the doubt, but Keeley seems (on and off screen) to have the personality of day-old Wonderbread. She may be lovely, but no matter how his friends try to sell this relationship, she’s jump-off arm candy, and a pretty dull one at that.

    • Pilar says:

      To be honest Harry is jump off arm candy as well so..

      • Enny says:

        @Pilar – true, but I’d never describe that guy as dull… 😉

      • Pilar says:

        I don’t know anything about her so I can’t say anything about her personality. And while Harry is somewhat charming he doesn’t strike me as particularly interesting. It feels like he is trying way too hard to cultivate this particular image he and his team have created and it all feels kinda forced so tbh I wouldn’t know who has the better personality in private. They both have nice bodies though 😂

      • Mia4s says:

        I wouldn’t call myself a fan, but he certainly has talent…however…I was reading something awhile back that referred to him as “Six Flags David Bowie” and I laughed myself sick. Now that’s all I can think about when I see him trying to pull off the androgynous rock star edge. Oh my dear, you are talented, but you’re not a patch on Bowie. Let’s not.

  3. Pilar says:

    Love his t shirt. While I don’t like this narrative I also think Olivia totally had Harry lined up as her jump off. She did the same thing with her ex husband years back with Jason so that’s her pattern.

    • Jenni says:

      I don’t think that’s true. She announced her separation from her husband in Feb. 2011, filed for divorce in Mar. 2011. She met Jason at an SNL after-party sometime in May or April 2011. But they didn’t start dating until November 2011. Both of them were seeing other people when they met.

  4. Chica says:

    Everyone acting like a person losing their spouse who they were very much in love with was and is the parent to their children is something that would be easy to deal with. They were not consciously uncoupled. This is human as af. And let’s not act like drowning your sorrows in a rebound relationship to save face or cope, isn’t a tale as old as time.

  5. Louisa says:

    I don’t remember her at all from Ted Lasso. Who was “Bex”?

    • Enny says:

      She went to the charity ball as Jamie Tartt’s 2nd +1 and then left with Rupert, to whom she is now engaged and with whom she is now expecting a baby. And yes, she’s bland af so it’s not surprising you’d miss her in a lineup of 1.

      • Mia4s says:

        “ not surprising you’d miss her in a lineup of 1.”

        It’s funny you say that because until my rewatch of the show, I had thought she was also the half-dressed girl that Keely meets in Jamie’s kitchen after they break up. She’s not! Oops. In fairness to the actress, that character serves a very particular purpose, but you are not wrong.

    • NorthernGirl_20 says:

      Rupert’s new wife – the one he had a baby with.

    • Johannita112 says:

      Rupert’s new girlfriend.

  6. mia girl says:

    I’m giving Sudeikis some slack about still being hurt, because it’s only just about a year (at least in his narrative) since she left him. And she moved on super quick and is all in with Styles. Some people take more time to get over things. It can’t help that there are so many videos of Wilde at Style’s concerts totally swooning over him. Even if Sudeikis trying out casual relationships, it must suck if he’s still in love with Wilde.

    • Cara Jane says:

      He has been with Keeley for about the same about of time she’s been w/ Harry though. They were first pictured together in February (only a few weeks after Harry and Olivia were first papped) and he accepted his Golden Globe from Keeley’s house. Given their longstanding friendship and Jason’s saying he’s always had an attraction to her, I have a feeling Jason already had Keeley on the brain when they split—and maybe even before then.

  7. superashes says:

    This whole story keeps confusing me simply because my favorite character in Ted Lasso is Keeley, who is not played by real Keeley, who instead plays Bex, but looks very much like show Keeley in real life.

  8. Cava24 says:

    I kind of side-eye anyone who identifies another human being as someone they aren’t serious about in a romantic relationship. It’s kind of hurtful and diminishes the other person. And it basically says one party has all the power in the relationship, which is gross. I get Jason being hurt still, I think the abruptness of the split, which I think was a long time coming (and there are signs Olivia was planning it for a long time, even if Jason didn’t realize it) but not executed until she had a jump off, (her jump off for her ex-husband was Ryan Gosling, not Jason), made the whole thing harder than it had to be.

  9. heidstar says:

    I knew Olivia and her ex-husband Tao back in the day when they lived in Venice Beach and we all would go to Burning Man together (where they got married in a bus when she was 19). I feel compelled to weigh in since everyone is side-eyeing Sudeikis’s narrative. Just FYI, she did the EXACT same thing to Tao and he was also devastated. I’m not sure if she left him for Sudeikis but I 100% know that she has never been single in her adult life and does whatever she wants regardless of others’ needs or feelings. She comes from a very privileged and massively intelligent family also, although she personally didn’t get any higher education as far as I know. Just … yeah.

    • Mia4s says:

      That’s the story I have heard about her as well, lines up a jump off and then is gone with little fanfare or care. Now my guess is she won’t be the one doing the leaving in this most recent relationship, and I am VERY curious how that will play out. I just wonder if the make it to when her movie that he is in eventually comes out. Holy Potential Awkwardness Batman!!

    • Cava24 says:

      Olivia and Tao got married at Burning Man? I think she left that out of the story when recounting it in interviews. She said they eloped and got married on a bus but not that it was at Burning Man.

      • heidstar says:

        @Cava24 and @Mia4s I heard she got married at Burning Man. But who knows! And yes, I am interested to see how the most recent relationship plays out for those reasons also …

  10. Lena says:

    Yes I wish he would just shut up about his heartbreak simply because they have kids and they don’t deserve to have their parents soap opera life plastered continuously over the tabloids. For that matter I wish Olivia would be a little more reserved publicly for the same reason.

    • Cava24 says:

      She will not get the increased visibility she clearly, clearly wants from this if she is discreet. I have never before seen pap pictures of anyone in their boyfriend’s branded merch like she has been doing for few months, except maybe Kim Kardashian.

  11. cassandra says:

    I was cool with the heartbreak stories initially. But it’s been a year, he’s riding a career high, and he has a public girlfriend. It’s not super believable now or necessary PR wise. Shut it down.

  12. Bobbie says:

    Guy just got out of an LTR and is still in mourning over his ex. Well, sign me up for that! I’d love to date him. 🙂

  13. Songs (Or it didnt happen) says:

    Im a little bit confused why people who take sides at all in this are on Team Olivia. If a man in a LTR broke it off suddenly, maayyybbe cheated and mayyybbee didn’t, then began dating someone younger that they had professional power over, we’d all be calling it icky AF. I guess I don’t understand why Jason is the bad guy in this narrative.

    • Jessica says:

      People on Team Olivia are a very small minority. But Jason is also dating someone ten years younger who he has professional power over. And his professional power is more concerning because 1) his show is still filming while Olivia’s movie is done, and 2) he has far more connections, money, and influence than Keeley whereas the reverse was true with Harry and Olivia. Olivia may have been his boss for four weeks while they were dating, but Harry had more constructive power in the relationship.

      And as I noted above, there’s equal reason to side-eye Jason’s relationship w/ Keeley as precipitating the split as there is Olivia’s relationship w/ Harry. Nothing is clear as to what happened, but I am weirded out by Jason trying so hard to craft a certain PR narrative when the public was already firmly on his side b/c of his character in Ted Lasso and b/c Olivia was the first to *publicly* move on. He didn’t need to throw Olivia under the bus to come out smelling like roses.

      • Pilar says:

        I see your point but tbh if it’s true that Jason and this woman were old friends and started dating after Olivia left him you can kind of see how people don’t react as badly to that as leaving the father of your kids for someone you just met on set..
        Also in terms of the daily dynamics on set, the relationship between actors and directors are much more vital to the movies well being .Olivia is supposed to lead the set and cultivate a professional atmosphere. If a director forms an intimate bond with one of the actors it’s gonna change the dynamics with the other actors and create and awkward uneven atmosphere.
        And Harry styles is not a major movie star ( despite what Olivia might be trying to tell us) He literally had one credit ( and a tiny part at that) prior to olivias movie so I don’t get this whole idea that he has as much or more power than Olivia. Star power yes. But that doesn’t necessarily translate to Hollywood box office power ( see Justin timberlake and many more). He’s very inexperienced as an actor.

  14. TrinaAnna says:

    I felt bad for Jason in the beginning but now I don’t. He’s been friends with Keeley since 2014. I think he is trying to make Olivia look bad. I think he was at fault too. He cheated on his first wife Kay. I still think they could of had some kind of affair. Him and Olivia were having problems and I heard he ignored her a lot when they were in LA. He or Keeley called the paps regarding those Cabo pics. Probably wanting to get Olivia jealous and show he isn’t alone on the holiday. I’m surprised he wasn’t with the kids. I read an interview with Keeley and she talked about wanting marriage, kids and live in London. I don’t see Jason uprooting his family for her. She might as well find someone else to hang out with if she wants something serious. I’m curious if she is still around after Ted Lasso finished filming the third season.

  15. Rita Fires says:

    Jason Sudeikis is so kind and thoughtful…the Internet is full of sweet and funny stories about him. I think he’s just a sensitive person who is still hurting. His PR team needs to lay off and let things just work out.

  16. KC says:

    Does Keely remind anyone else of Kelly Brook? I can’t figure out what it is.

  17. LynneF says:

    It’s amazing how much interest there is in Jason Sudeikis and Olivia Wilde since their split. Before their split they seemed to be a really cool, low key couple.
    Re Olivia: it seems she is trying to recapture her lost 20’s she missed by marrying young? She seems to be having a lot of fun with Harry. I do wonder why she jumps from one serious relationship to the next with no time for reflection.
    Re: Jason Sudeikis, he seemed genuinely blindsided by his split. His relationship with Keeley seems casual and he is taking the time to heal and grow before jumping into another serious relationship.
    They both very talented and deserve happiness in their personal and professional lives!