Olivia Wilde & Jason Sudeikis broke up & ended their 8-year engagement

25th Annual Critics' Choice Awards

This photo ^ says a lot in retrospect, right? The last time Olivia Wilde and Jason Sudeikis appeared together at an event was the Critics Choice Awards in January. Olivia was there representing Booksmart, the film she directed. As she moved more into producing and directing, it did feel like… I don’t know, there was more space between them. That being said, I never paid too much attention to their relationship either way, because they just seemed like an odd couple from the start. And now it looks like they’re over, per a People Magazine exclusive:

Olivia Wilde and Jason Sudeikis are going their separate ways. The Booksmart director, 36, and the Ted Lasso star, 45, have split, ending their engagement of more than seven years, PEOPLE has exclusively learned.

“The split happened at the beginning of the year,” a source close to the couple tells PEOPLE. “It’s been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship.”

Wilde and Sudeikis share son Otis Alexander, 6, and daughter Daisy Josephine, 4.

The pair first started dating in November 2011 and Sudeikis proposed shortly after the holidays in 2012.

[From People]

Yeah, they were one of those “permanently engaged” couples. After two kids and nine years together, you would think they would just call each other husband and wife or partners or something. Anyway, I didn’t think they would last as long as they did, so congrats on that. I have zero to back this up, but I have a feeling that Olivia probably has a jumpoff waiting in the wings. After her first marriage – to an Italian prince – crashed out, she talked about it and kind of shaded him publicly. I wonder if she’ll do the same this time, or if things are different with kids in the mix.

"Booksmart" Premiere

Photos courtesy of Avalon Red.

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77 Responses to “Olivia Wilde & Jason Sudeikis broke up & ended their 8-year engagement”

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  1. Seraphina says:

    Yeah, this couple was a strange pairing for me but that made me like them even more. I do feel for the kids. I hope they are able to provide a healthy environment for them as they go their separate ways.

  2. Silver Charm says:

    I guess the only surprising thing about this is the timing. She just started filming her next movie and is think she’d want the focus to be on that. I agree, someone has a jump off.

  3. K-Peace says:

    I’ve always found him attractive for some reason. In fact he’s one of my very few “celebrity crushes”. I wonder what went wrong between them. They always seemed very happy together.

    • SamC says:

      Friend of mine is MUA and worked with him a few times. Said he was really nice, easygoing. She got to hang out with him and Jason Bateman for a few hours on one of the projects and all of her friends were massively jealous!

    • minx says:

      I liked them as a couple, they seemed different yet compatible. Did wonder why they were engaged for so long and never got married, but now it seems like the right move.

      • Wiglet Watcher says:

        This might be another quarantine divorce/separation.

        I never saw the compatibility. He had and has success and his name carried. She had House recognition and some movies, but they weren’t anything memorable or decent. And it seemed her career would get the huge boost from him and his connections.
        That aside they also seemed like 2 very attractive people that were together, but not a long term couple.

      • Carol says:

        I really liked them as a couple and I had hoped they would have made it together. They seemed to have respected each other and their work – at least it appeared that way in all of their interviews – and from all I’ve read of them, they seemed like very nice, unhollywoody folks. Too bad.

  4. Sara says:

    She was cruel to her 1st husband in the press. I hope she will not repeat this time.

    • Lori says:

      Yes! I was wondering if her vagina had died again.

    • Wiglet Watcher says:

      She couldn’t take that path again if she wanted to. His reputation and PR game would leave her frozen out.

    • Lucy2 says:

      I always found her very annoying, and I think it leads back to how she behaved in the press regarding that marriage.

      However, she seems to have really matured, and now that there are kids involved, I think it will be different.
      Booksmart was excellent, and has changed my opinion on her.

    • Elle says:

      I think somebody overheard a conversation she had with friends in a bar and leaked it to the press. She never intended to badmouth her first marriage. I don’t think it’s fair that she gets such a bad wrap just because some a*hole decided to share that to the world without her consent.

      • Jess says:

        No she was at a public event with an audience when she talked about her vagina dying. I think it was supposed to be a joke or meant to empower women, but she came off like an asshole.

    • Mrs.Krabapple says:

      Speaking of her ex husband, I just wanted to say he was NOT a prince. Italy does not recognize those titles in any way, so YOU could call yourself a Prince and it would have the same legal effect: nothing. But even IF they still recognized these titles (which they don’t), illegitimate kids did not get titles, so her ex STILL would never have been a prince. The only thing worse than actual royalty giving themselves airs as if they’re better than others just because of a title, are FAKE royalty trying to do the same.

  5. Cava24 says:

    Her IG has been all about her shift to being a director, and figuring out what she wants and how to contribute to the various communities she is in. She seems like an emotionally generous person. I don’t know that Sudeikis can keep up with her, he seems like someone who wants an audience for whatever he is doing and …. he’s not trying to be much beyond that. Cue him being back in Aniston’s orbit. It would not shock me if her jump off was female. That said, she, is working with Harry Styles right now (or was, their set was shut down because of a COVID case), he wouldn’t shock me as a jump off either because there is a lot of overlap in their outlook.

    • Millennial says:

      Yeah I think she’s signed on to direct a Marvel movie now. I think she’s just getting busier/more work, and with his work commitments too I’m not sure she wants to have to schedule her career around his. Their relationship dynamics changed, is my take on it.

      • TJ says:

        She is attached to direct FOUR movies in the near future, so yeah she can be very busy, very soon. She is also playing in Don’t worry Darling.

    • Tiffany :) says:

      “She seems like an emotionally generous person.”

      I have 2 different friends that know her from different circles, and both have nothing but good things to say about her as a friend. She seems very kind, fun and nurturing.

  6. Iris says:

    I don’t know if I’d agree with that analysis of Sudekis, @cava24. Have you watched Ted Lasso? It’s one of the best things I’ve watched this year. It’s kind and warm and it made me want to be a better person.

    I’m sad about this, I liked them together

    • NEENA ZEE says:

      +1
      Ted Lasso is one of my favorite pandemic binges. It was smart, funny, sweet, totally heartwarming. I want everyone to watch it!!

    • Cava24 says:

      I think he has warmth and empathy but a lot of boundaries around who he connects with and how he supports them. She seems okay with messy work around trying to be a better human, he seems more rigid (might be the Midwestern thing, I am from the Midwest and have found a lot of people to be like that but also empathetic around things like loss, adversity that is out of someone’s control, just less around emotional struggle).

    • Green Desert says:

      Agree Iris, Ted Lasso is so great and a wonderful warm blanket for these times. After I heard this breakup news I thought about his (Ted’s) storyline with his wife on the show and how heartbreaking that was. I wonder if his real life mirrored that.

      • AMAyson1977 says:

        We just started Ted Lasso and are “rationing” it because it’s so good. I wish there were 3-4+ seasons! It’s so good that I want to binge, but I don’t want it to be over. Highly, highly recommend.

  7. Kaye says:

    They have such cute kids! Wish them well……Harry styles?! Whoa would make for great gossip!

  8. g says:

    i don’t buy the timing here, they both spoke about each other as partners way past the beginning of the year

    • TJ says:

      Yep, me either. I saw paparazzi pictures from them in early September, where they had a ton of silly fun with each other at a beach in LA.

      • Meg says:

        Maybe they said they separated at the start of the year because they’re concerned old pics may be coming out of one or both of them with others and they don’t want accusations of cheating to come out?

      • julia says:

        Agreed – her Valentine’s day post on IG of this year also reads like they (or at least she) was still very much in love.

  9. FrenchGirl says:

    He works on Ted Lasso who filmed in England whereas she becomes director in USA.

  10. Also Ali says:

    Since no one was asking for this information and it happened a year ago with no one noticing, my guess is one of them is about to be seen in public with someone new.

    • Nikki* says:

      I think you might be right!

      • TJ says:

        I don’t buy that time table. As I said Olivia wore her engagement ring yesterday! She wore all year long, I checked some pictures. That’s very odd if they broke up very early this year,

  11. TJ says:

    I’m not 100% sure they are split yet. Olivia still wore her engagament ring from Jason on the paparazzi pictures taken from her (& their lovely kids) – yesterday. Also yesterday she tweeted support on Jason’s charity concert in Kansas(Thundergong), which he liked (yes he had twitter to, but only use it to like tweets & following people). And he gave Olivia a shoutout (as Ted Lasso) on that concert calling her (in character) “his favorite director, who’s easy on the eye” & dedicated the song “Patience” by Guns N’ Roses to her.
    These things all happened in the last 24 hours. Maybe they are not done yet with each other as a couple?

    • Cava24 says:

      She may have waited until they were ready to announce to take the ring off (assuming she takes it off). A lot of people don’t announce until they have worked through custody, asset split etc if it is amicable. COVID may have delayed things too as it impacted their childcare situation. They might be able to comfortably cohabitate but not be romantic partners.

  12. Michael says:

    Oliva really was cruel to her ex-husband but I am not sure if she was intentionally cruel or if it just slipped out due to hurt feelings. They did hang out after they split up so maybe they made up at some point. She is older and wiser now so I suspect she will be silent about her breakup. I have nothing for or against either of these two so best of luck to them both I guess

  13. Badgerette86 says:

    @iris your comment about Ted lasso is bang on! That show was a savior for my belief in humanity being good- after this year. Can’t recommend the show enough!

  14. nicegirl says:

    Awww, I thought they were kinda cute together. Maybe it’s for the best?

  15. Lily says:

    There’s a very telling piece from 2012’s Vulture called, “Olivia Wilde Said a Great Many Things About Her Vagina Last Night“.

    Such as… in her ideal world, relationships can only last 7 years.

    Also, when intimacy declines, it’s time to get out of the relationship because, “there’s no reason to sacrifice your womanhood and femininity for some sort of weird feeling of responsibility on something that may not be right”.

    There are many people who marry young and feel trapped, and never want to marry or feel trapped again. Olivia seems to be one of these people.

    • TJ says:

      She admited that piece was a joke. Also said it was not intended to the public. Yet people stillmentioning that thing over & over again. While her ex-husband is still following her on instagram & twitter

      • Wiglet Watcher says:

        All jokes are rooted in truth by those telling.
        J/s

      • kat says:

        It was a public monologue. In a pub. In NYC. She can say what she wants about her vagina, but this was not something private that got leaked. The event was hosted by a magazine so of course there is going to be press about it. I believe Sudeikas, who she was dating at the time, was in the audience, just to add a twist.

    • Sean says:

      I just googled this Vulture article. Her monologue may have been intended to be humorous but it sounds like it came from a place of pain. This was eight years ago and I hope she’s in a better place now. We don’t know what happened during her first marriage nor in her relationship with Jason.

  16. Savannah says:

    I can relate. I have no desire to get married but I love my partner. Some people just don’t want marriage.

    • Jayna says:

      Cool. Just be partners. But that’s not what they did. They got engaged to be married and both talked about marriage and setting or not setting dates in interviews over the years.

      • lillyfromLilloet says:

        This, @Jayna! They got engaged and didn’t get married, they had a kid and didn’t get married, they had another kid and didn’t get married. This has felt like a relationship that they wanted to be it for them, but there was something that kept them from actually making good on the engagement. I wouldn’t be surprised if they still make ambivalent signs, like ring wearing, speaking of being together, of affection for each other. And remember the statement in People said that they had split months and months ago–likely because it was a trial and they wanted to see if they really did want to split, and COVID likely threw in some unexpected elements. I think they really tried and waited and etc, but they are superdone trying to make it work.

  17. Jayna says:

    I underestimated her. She’s really a better actress than I thought she was. I saw her in a bad movie, but she was great. But where I really underestimated her was her obvious talent as a director and drive.

    I’ve always been fond of Sudekis. Every time he’s in a movie I’m surprised by how much I like him in a movie, even average ones.

    I liked them as a couple.

    • Wiglet Watcher says:

      We never got to see if she was actually a good actress because her roles were awful. I lean towards her being stunning with mild talent in regards to acting. I think she’s far better suited for writing/directing/producing.

      • TJ says:

        Her problem is that almost nobody watched the movies she is rrrrreally good. Drinking Buddies, Meadowland, A Vigalante(all of them are over 80% at Rotten Tomatoes). Outside of maybe Drinking Buddies almost nobody heard about this films, yet she is very good of them all. She is very underrated as an actress.

      • Wiglet Watcher says:

        Tj
        If a movie is good and the actor in even a bad movie is reeeaaalllyy good it gets out.
        She also had her name attached to a few box office bombs. That doesn’t help.

        Not many heard of Rachel Getting Married until Anne Hathaway showed her skill as an actor. I’ll maintain that even a terrible film can be carried if an actor is talented enough. Bonus if they have name recognition which she did and does because that makes it easier to promote.
        I don’t think acting is her talent and I think she’d prefer to be behind the camera. And I think she’s an amazingly skilled writer, director and producer.

  18. Nikki* says:

    I thought they were married!

  19. Case says:

    This one made me sad. They were a really cute couple. Hope they’re able to keep it friendly for the kids.

    I’ve liked Olivia since House (she’s still one of the most beautiful women I’ve ever seen!) and LOVED Booksmart, so I’m really excited to see her future directorial projects.

  20. bobafelty says:

    I just saw him on a tv interview. He’s working to fundraise for a group that creates prosthetics for people who otherwise can’t afford them. He seemed really passionate about it, and it made me think more highly of him. Really hoping he doesn’t have some side piece or something, I want to keep liking him!

    • Dazed and confused says:

      He does a lot for charity. He’s from the Kansas City area and comes back here regularly to support the city. He raises a lot each year for the local Children’s Mercy Hospital with The Big Slick, with other celebrities who grew up here: Rob Riggle, Paul Rudd, Eric Stonestreet, and David Koechner. Thhey are all very generous with their time and come here often. I think that says a lot about him.

  21. Sorella says:

    I like them both, but they did seem odd together, but they did make it work 10 years and 2 kids later. But I side-eye anybody who has a long engagement like this – anything past 3 years is never gonna happen in my opinion. I see him with Jennifer Aniston – they would go well together. And imagine if she got together with Brad Pitt lol (which strangely, I can see her with him too).

    • Ange says:

      My brother has been engaged to his partner basically since I got together with my husband, so nearly a decade. They’re certainly never going to get married and I imagine it’s the same for a lot of people who do that. I guess the big thing is whether or not both people are ok with the situation and whether or not it’s being used as a stalling tactic to avoid dealing with some deeper issues. I’m fairly sure all parties are ok with it in my bro’s case but I bet plenty aren’t.

      • Jenn says:

        That makes a lot of sense to me! I definitely know people who are in committed-but-unmarried long-term relationships, and for them it seems like a marriage certificate would honestly just kind of ruin things. I imagine that for those partnerships, it’s the knowing that any party can leave at any time — but all parties simply resolve not to — that makes the actual commitment really meaningful and worth honoring. (There’s this beautiful Tom Robbins quote, “I love you for free.”)

        As for me, I’d always been a huuuuge commitmentphobe. My husband wrung a marriage contract out of me *fast*, so that I’d have a legal obligation to try to make things work, instead of throwing up my hands and walking!! I know that doesn’t exactly sound romantic, but I feel like the conventional institution of marriage still works for people like me who can be brash.

  22. Keats says:

    Didn’t Jason’s ex tweet about him (without naming him) reading some pick-up artist book and telling her not to worry about it? A few months before he dumped her for Olivia? I can’t work up enough energy to dislike him but I think he’s a bit shady.

    • Keats says:

      Her tweet was in response to a question like “what was a relationship red flag that you ignored at the time?” And she responded “Mine was when I saw him in bed reading “The Game” just “to see what it was all about.”" Then clarified later “(we were married)” so yeah. Not expressly a fan of his!

    • Jayna says:

      He didn’t dump her for Olivia. He was seen out with other women after his split. He was seen out with Scarlett Johanssen. Although, she called it a friendly outing, not dating. He dated January Jones also after his divorce.

      Jason’s ex-wife is extremely talented herself and successful in the business as a writer and has directed.

  23. Severine says:

    I’m old and not as hip as I’d like to be. Hence, my next statement. Who the hell stays “engaged” for 8 years? Engagement is supposed to be a transition to marriage, not a place holder to legitimize what is actually a boyfriend-girlfriend relationship. You are close enough to this person to reproduce twice with them, but not close enough to marry them? I know you don’t need marriage to have children. Now they can tell their kids “Oh, we were engaged to be married, and you were “so” wanted blah blah blah” instead of saying “This is just someone I enjoyed screwing around with and we ended up having you two kids together, but we want you to think it was more than that so we were ‘engaged’”. I am so tired of this story line. It would actually be refreshing if they just owned up to the fact that they never had any intention of marrying each other.

    • Jenn says:

      I mean, why does any relationship end? The love might be there, but sometimes people just want different things out of life. Sometimes people get engaged too fast because they’re very much in love and have every intention of marriage, and then they try to ignore the fact that they don’t actually work that well together, but they sense something is wrong, so the engagement drags on and on. Have you ever met a couple that isn’t even engaged yet, but they already spend a lot of time in therapy?

      There are also people who don’t want to get married until everything is “perfect”; I was that way, and if I’d kept to that, I would still not be married, because I am not a perfect person. None of this means that their children were any less “wanted” than a married couple’s. (I highly doubt they were engaged just to give their kids “legitimacy,” since we do not actually live in a Dickensian novel.)

  24. Courtney B says:

    Side note but I wish he would come back to SNL to play joe Biden again. I always laughed at his take. I really don’t like Jim Carrey’s. It doesn’t resemble Biden at all.

    • Lucy2 says:

      I agree, I think his Biden is the best. I really hate Jim Carrey ‘s.

    • LaurenMichelle says:

      I recently saw Jason’s Joe Biden persona on old SNL clips. Hilarious. Also his Regine skit was brilliant. Jason never breaks character. Olivia is a decent actress and gorgeous. I liked Jason and Olivia together. Such a shame they split up.

  25. SJ Knows says:

    I don’t like her from the interviews I’ve seen her in.

    Maybe they just wanted to have kids together, not everybody wants to be married. I figure if an engagement does not turn into married within about 3 years..it’s a no go.

  26. HeyJude says:

    I saw this one coming, she’s on the come up big time in directing and producing. She’s done good work, is already known from acting, and is marketable- she’s being lined up for big things in that end as she’s landed a deal to direct a Marvel project. She’s on the path to eclipsing him as the bigger success.

    He hasn’t done a lot recently film wise and is back on (streaming) TV, too in contrast.

    And no matter how much more well known a name he might be, he ain’t no Marvel director. That’s a whole other level of power in Hollywood.

    She’s very much becoming an auteur and he’s still doing the same not so serious funnyman thing, that involves divergent paths, interests, colleagues/friends.

    • Jayna says:

      Agreed. And also more time away from each other. In that kind of business, you film in different places. He is back to streaming TV, but he is one of the creators and producers of his TV show, and it’s a huge hit for Apple TV since it premiered in August. They’ve already renewed it for season 2 and season 3 it is so successful for them.

    • So What says:

      Yes, women don’t respect men when they are more successful.

  27. Sunnyvale says:

    Wow I thought they were married! I havent seen her in anything except that strange movie with Liam Neeson when she was photographed by paparazzi tying his shoes and I cant remember when I last saw his work! Its sad for the kids but I hope they get along after separating for their sake. I agree with others, this feels like they grew apart because they are on different levels professionally and I wont be suprised to hear news of him dating a costars soon!

  28. TalkingVag says:

    The (video) camera absolutely loves her. She’s got the charisma and looks (amazing eyes and skin in moving imagery) but got caught in ingenue roles. Tron, Cowboys and Aliens, that film with Eric Bana, and a tiny role in The Next Few Days (Russell Crowe). Be interesting to see her directorial vehicles.

  29. Saki says:

    This makes me sad. They seemed like a low-key family and respectful of each other.

  30. Blackbetty says:

    Sad I like these two.

  31. Enny says:

    Maybe she realized she couldn’t be married to the monster who punched Baby Yoda. 😉

  32. PixiePaperdroll says:

    I think he’s more likely to have someone else lined up. I believe he is in the speculative list of men who knocked January Jones.

    (Which makes me sad because I LOVE HIM.)

  33. Mars says:

    Without make up she’s above-average, and I never found him funny.