Hollywood's it couple, Jason Sudeikis and Olivia Wilde, hit the gossip mill when they announced their split. After being an item for nearly a decade, we were even more shook when explosive secrets began emerging about the separation...
Where It All Started
While Wilde and Sudeikis may be two of Hollywood's biggest names, it wasn't always that way. Before they made making headlines or even got their start in acting, the two were just two regular folks with dreams of making it big.
For Wilde, the Georgetown native, it was a role on House as Remy "Thirteen" Hadley that put her on the map. On the other hand, it was SNL and a writing gig for Sudeikis, hailing from Kansas, that proved to be his real lucky break. This is where their story begins...
Justin Timberlake hosted the epic season 36 finale of Saturday Night Live, and Lady Gaga provided the musical entertainment. There was a lot to celebrate, and actors Olivia Wilde and Jason Sudeikis both attended the after-party, where sparks soon flew. "I met her at a finale party for SNL. We hit it off that night," Sudeikis recalled.
According to Sudeikis, he and Wilde hit it off on the night - but it wasn't his jokes or even his smile that drew her in; it was his moves! As Wilde confirmed in an interview with Allure years later, "I met Jason, and I thought he was so charming. He's a great dancer and I'm a sucker for great dancers. But he didn't even get my number." For now...
Head Over Heels
After Jason Sudeikis was given Olivia Wildes' number by a mutual friend, she was convinced something really bad had happened when no texts came after a whole month. She even went so far as to tell her friends she thought he'd died! Eventually, he finally got in touch, and the long-awaited first date ensued.
It lasted until 2 am, and the actress grew concerned that he wouldn't like her, but luckily it seemed those worries were unfounded. When Wilde revealed what happened to Howard Stern later on, she recalled how "He didn't kiss me until the fourth date. He finally kissed me. And I was like, completely head over heels."
The Big Move
Olivia Wilde and her rescue pup, Paco, soon decided to take the plunge and move cross-country for love. They said bye to the sandy beaches of Los Angeles and hello to the hustle and bustle of New York City, ready to make a home with her partner, Sudeikis. And it seemed like she was enjoying every minute of it!
Wilde told USA Today how much fun she was having making their new place into a home - painting walls, setting up furniture, and even getting an electronic drum kit. "I've been decorating our new apartment. That's a lot of what I do, too. I'm so domestic. We have a cool new electronic drum kit," she shared. "It's a good life."
When Jason Sudeikis and Olivia Wilde began dating, they likely had thoughts of marriage in the back of their minds. Luckily for us, they realized that life is too short - and in 2012, Sudeikis put a ring on it! The elegant emerald ring encircling a diamond was the perfect choice to show off Wilde's timeless style.
Even though they weren't sure when they'd get married, Wilde had her sights set on NYC. "I don't know when we're going to get married, but it doesn't matter because we're going to be together forever," she told Marie Claire. "My dream is to have it close to New York. I love dressing up, and I want to design my own dress."
Love was in the air for Olivia Wilde and fiancé Jason Sudeikis when they worked together on her 2013 film Drinking Buddies. Wilde had invited her fiancé to join her on set, and her luck turned when she asked him if he would play her boss while practicing lines.
Despite being busy filming We're the Millers, Sudeikis agreed, and the couple got to act and work together in a comedic environment. "We roped him in... He came to lunch onset, and I was like, 'Listen, we don't have anyone to play my boss, will you just jump in and improvise with me for an hour?'" Wilde recalled.
In October 2013, Olivia Wilde and Jason Sudeikis had plenty of reason to celebrate: they were expecting their first child! A source close to the couple shared that they were "incredibly happy. They're very excited to welcome a new member into their family," PEOPLE reported. Sure enough, 9 months later, Otis Alexander Sudeikis came into the world.
Wilde commemorated Otis' arrival with a tweet that was too darling not to share - "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building!" All joking aside, it's clear these two were taking parenting seriously as they looked forward to watching their little bundle of joy grow.
After many years of being in love, Wilde and her partner had decided that the next step was a wedding - but when would they actually make it happen? Well, in an interview with Glamour, Wilde revealed that "We're engaged, but no specific plans yet—we just have to find the time to put it together."
This wasn't too much of an issue for the couple though since they had already formed a loving family unit with their son and were soon expecting another addition. "In many ways, a child is more of a commitment. We are fully committed and really happy as a family," she shared.
Jason Sudeikis and Olivia Wilde had a lot to be excited about when April 2016 rolled around. Wilde posted a photo of the couple with their son Otis's "matching baby bumps" - because she and Jason were expecting again! On October 11, 2016, Wilde gave birth to their baby girl Daisy Josephine Sudeikis, who was born on International Girl Day.
After getting home from the hospital, Wilde shared an adorable picture of Daisy on Instagram, joking that "there goes the neighborhood." With a heart emoji at the end, it was clear Olivia felt thankful for the addition to their family - and that they fully embraced girl power!
With two kids and demanding work schedules, you'd think Olivia Wilde and Jason Sudeikis had little time for "date night," - but this energetic couple proved otherwise. Whether it was sharing adorable PDA posts on social media or singing each other's praises during interviews, these two were truly living it up.
In fact, Wilde revealed the secret to maintaining such a fiery flame - they keep it interesting by trying new activities. "We prioritize date night," she noted to Us Weekly. "We go out and have a lot of fun." And if that wasn't enough, here's where things were about to get even more fun for Wilde and Sudeikis...
In the Director's Seat
Olivia Wilde was embarking on a brave new venture and stepping into the director's chair for her first feature-length film. Despite having experience directing music videos for Edward Sharpe and the Magnetic Zeroes, and the Red Hot Chili Peppers, this was an immense task in comparison.
Booksmart told a story of two friends who had spent their high school years studying and were now scrambling to make up for lost time by partying. With performances from Beanie Feldstein and Kaitlyn Dever, as well as a hilarious cameo from SNL's Sudeikis, it was a successful debut for Wilde that grossed over $25 million at the box office!
Don't Worry Darling
After the success of her directorial debut, Olivia Wilde was already in high demand. Everyone wanted a piece of her second project – Don't Worry Darling. A psych thriller with two writers, it quickly became part of a massive bidding war with an incredible 18 different studios interested.
Luckily for Wilde, she was able to make a decision on what studio would be best suited… and she chose New Line Cinema; the only studio that guaranteed a theatrical release. “I suddenly had the opportunity to make the decision of what would be the best home for us,” Wilde recalled of the decision.
The news of the cast for the upcoming project had everyone buzzing with anticipation, and it didn't let up when the casting was announced: Florence Pugh from Midsommar and Shia LaBeouf from Transformers were to be the leads. Pugh took to social media to share her excitement, but then a surprise came - LaBeouf was out.
"I tried to mediate a situation… to try to see if they could work together," Wilde explained of the decision. "Once it became clear that it was not a tenable working relationship, I was given an ultimatum." And so, Harry Styles was brought aboard instead. "We found the perfect Jack… it's kind of magical that it ended up being our first choice."
But things at home weren't as "magical." By November 2020, the end of Olivia Wilde and Jason Sudeikis' relationship was an absolute shock to fans, leaving them wondering what could have happened. In a GQ interview, the actor seemed to be just as bewildered by the sudden split.
Reflecting on the situation, Sudeikis revealed he'll "have a better understanding of why in a year." He added, "And an even better one in two, and an even greater one in five, and it'll go from being, you know, a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle."
On the Rebound
Following her split from her long-time partner, Olivia Wilde was spotted with the star of her latest film, Harry Styles. In January 2021, they made an appearance together at a wedding, and a source even stated Styles referred to Wilde as his "girlfriend." Speculation was running wild over what had been going on between the pair.
Despite the gossip, though, in later weeks, Wilde reappeared at Styles' LA home with photo evidence to back up the relationship rumors. It seemed to confirm Olivia Wilde's split from her former fiance - and things were heating up with Harry, fast!
Behind the Scenes
After months of hard work and countless behind-the-scenes shenanigans, the cast of Don't Worry Darling took a celebratory group photo to mark the end of filming. Little did they realize that this was just the beginning of the drama that was about to unfold.
Lead star Olivia Wilde made a post dedicated to her new man, praising how Styles "…infused every scene with a nuanced sense of humanity." On top of it all, former beau Jason Sudeikis also moved on to date British model Keeley Hazell, who had a small part in his film Horrible Bosses 2. Lots of changes were happening here.
Ambushed on Stage
At first glance, it seemed like both exes had moved on. That was, until a mysterious envelope was handed to Wilde while on stage at Vegas's CinemaCon promoting Don't Worry Darling. She assumed it was a new script and eagerly opened it right then and there. Reality soon set in, however, when she realized what it was...
The document was actually custody papers regarding her 2 kids - turning the event into a nightmare. Speaking to Variety, she said, "It was my workplace... in any other workplace, it would be seen as an attack." She added, "It was really upsetting. It shouldn't have been able to happen. There was a huge breach in security, which is really scary. "
Fueling the Flames
But more drama was on the horizon: fans began speculating about tension between Wilde and Pugh after spotting odd behavior on social media. There were also reports of a big gap in the two actresses' salaries for the movie, with Page Six reporting that the Little Women star was "upset" over Wilde's fling with fellow cast member Styles.
When asked about these rumors during an interview with Variety, Wilde referred to them as nothing more than "clickbait." While she never explicitly denied any sort of rivalry between herself and Pugh, she went on to praise her co-star. She even made a comment about how tabloids tend to "pit women against one another..."
Following the alleged drama with Pugh, LaBeouf soon emerged to share his take on things. Through a series of screenshotted messages sent to Wilde and forwarded to Variety, LaBeouf provided insight into why he left the film. He claimed that the rehearsal timeline was too rushed and he "couldn't find time" to prepare.
"You and I both know the reasons for my exit. I quit your film because your actors and I couldn't find time to rehearse," he had written. In addition to these remarks, a video of Wilde voicing her concerns about the actor's exit also leaked. Wilde was also heard calling it "a wake-up call for Miss Flo." Clearly, there were 2 sides to the story.
No Longer Speaking
Olivia Wilde was clearly no stranger to rising above drama. Even though the actress was already in the middle of a demanding press tour for her new film, she still had to face up to her complicated home life. After being served papers in public, she was taken aback. Wilde "was surprised and embarrassed," reported PEOPLE.
The source added that after the envelope saga, "She and Jason don't speak to each other, so they have help communicating about the custody schedule." Nonetheless, Olivia "wanted to focus on what's best for the kids," the insider concluded. Sadly, there was more chaos on the horizon.
Despite Florence Pugh's absence from Don't Worry Darling's photocall and press at the Venice Film Festival, director Olivia Wilde confidently addressed questions about the lead actress' mysterious absence - citing prior filming obligations and declining to comment on tabloid gossip.
Later, Pugh made her highly-anticipated red carpet debut at the festival - and her stylist teased Wilde's video with a shady Instagram post, captioned "Miss Flo." Fans also began to speculate that Styles had spit on Chris Pine that night, in what they called #Spitgate.
"Very Bumpy Road"
After months of gossip, Wilde finally addressed all the rumors in a September 2022 feature with Vanity Fair. She clarified that her relationship with Sudeikis had ended long before she dated Styles. "The complete horse**** idea that I left Jason for Harry is completely inaccurate," she swore. "Our relationship was over long before I met Harry."
She touched further on what led to their separation. "Like any relationship that ends, it doesn't end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic," Wilde continued. "We were raising two kids during lockdown, so we co-parented through that time."
The Crew's Take
In recent news, a seemingly interesting story has been unfolding surrounding the movie set of Don't Worry Darling. Everyone has been talking about it, as Vulture reported screaming matches between Wilde and Pugh, with the director and Styles having suspiciously long breaks from set.
Apparently, enough was enough for the movie's crew as they released a statement to PEOPLE disagreeing with the claims. "Any allegations about unprofessional behavior on the set of Don't Worry Darling are completely false," they assured. Had the press gotten it all wrong?
Late in 2022, both Wilde and Sudeikis faced a daunting decision: their custody battle had reached its end. The court sided with Olivia, claiming the children's home was in Los Angeles, so the family must continue the trial within California. And Sudeikis had lots to say on the matter.
Not only did he regret the chain of events surrounding their custody battle, but he claimed he "did not want service to take place at the children's school because parents might be present" regarding the CinemaCon saga. Going forward, it was important for both parents to remain civil and supportive in order to give their children stability.
The Nanny's Tell-All
The nanny certainly had some wild stories to tell about the events that led up to Sudeikis and Wilde's split. Ericka Genaro was a firsthand witness, so when their former nanny spoke with the Daily Mail in October 2022, it felt like we were getting an inside scoop on what really went down.
Apparently, Sudeikis once hopped underneath Wilde's car when she was leaving to try and see Styles.! Further claims included Jason only learning of Wilde's fling with Styles after he found messages on her forgotten Apple Watch. Apparently, he was an emotional wreck, "crying a lot, crying and crying." She also shared unseen text messages.
Laughing It Off
Sudeikis and Wilde weren't wasting any time when responding to their former nanny's claims. They released a joint statement, calling out their accuser. "As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make such false and scurrilous accusations about us publicly," they wrote.
It's clear that there was no amount of backing down from either side. "Her now 18-month long campaign of harassing us, as well as loved ones, close friends, and colleagues, has reached its unfortunate apex," the exes continued. We may never know what really happened, but something tells us this saga is far from over.
As It Was
Despite all the drama, Wilde and Styles' love story was still playing out - especially with their flashy romantic getaways. After Harry dropped his latest album, Harry's House, rumors swirled that some of the songs were about Olivia. Particularly, a line saying, "Leave America, two kids follow her," implying their fling had reached a new level.
But all good things come to an end, and in November 2022, roughly 2 years after they first started dating, the couple decided to take a break. Sources close to the stars assured PEOPLE that despite parting ways romantically, "They're still very close friends."
As for where Olivia and her other ex stand today? Reports of an Olivia Wilde-Jason Sudeikis reconciliation came January 2023, after the two were spotted hugging. As the co-parents navigate their post-breakup life, it appears that things are going relatively well between them.
According to an ET source, Wilde has been "focusing all her energy on her kids and family since her split with Harry, and now that they're broken up, it's been easier for Jason and Olivia to get along." Unfortunately, their latest chapter was about to hit another road bump.
More Legal Woes
In February 2023, Genaro filed a wrongful termination suit against Sudeikis and Wilde at the Los Angeles Superior Court. She is reportedly suing for a plethora of damages, such as medical expenses, loss of earnings, and more - plus unquantifiable suffering experienced after her firing.
To make matters worse, Genaro claimed that when Wilde left their home, Sudeikis turned to her for support. The famous exes struck back with a statement, claiming they "will continue to focus on raising and protecting our children with the sincere hope that she will now choose to leave our family alone." Yikes.
Since their relationship first began, it's like we've been on a wild rollercoaster. Every twist and turn of Wilde and Sudeikis' love story has captivated Hollywood, from their adorable meeting to their high-profile split. While plenty of questions remain unanswered about the couple's future, there's one thing that we can all agree on…
This saga is anything but over. While they try to figure out how to navigate the waters ahead, listen closely. We could be hearing more shocking news in the coming weeks and months. So keep your eyes peeled for further updates as this relationship drama continues.