They were Hollywood's it couple. Jason Sudeikis and Olivia Wilde were together for nearly a decade before things came to a dramatic end. But after calling it quits, new details came to light that left us with many questions...
The Start of It All
Before they made headlines or even became actors, Olivia Wilde and Jason Sudeikis were two regular people trying to make it big in Hollywood. Wilde grew up in Georgetown, while Sudeikis hailed from Kansas.
Granted, Wilde had nabbed a few minor roles. But it wasn't until she landed Remy "Thirteen" Hadley in the medical drama House that she got her big break. Meanwhile, Sudeikis started out performing improv and got his big break when he was hired as a writer on Saturday Night Live. This is where the story begins.
Saturday Night Antics
Live from New York. It's Saturday night! It was the end of season 36 of the famed comedy show. Justin Timberlake hosted the SNL finale with musical guest Lady Gaga. Wilde and Sudeikis both attended the finale after-party. Sudeikis later recalled to Stephen Colbert, "I met her at a finale party for SNL. We hit it off that night."
They certainly did. Even Wilde admitted that it wasn't his hilarious jokes or his fantastic smile that intrigued her. It was his dance moves! She told Allure, "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." Things were about to change...
Once Sudeikis got her number from a mutual friend, Wilde expected to hear from him immediately. It took an entire month to go by before he texted. The Cowboys & Aliens actress was so concerned that she recalled telling her friends, "I was like, 'You guys, did Jason Sudeikis die, because I don't have any texts."
Finally, Sudeikis texted her, and they went on their first date. They ended up staying out until 2 am, but Wilde was worried that Sudeikis wouldn't like her. But, of course, he was charmed. Wilde told Howard Stern, "He didn't kiss me until the fourth date. He finally kissed me. And I was like, completely head over heels."
Not only was she head over heels, but she was also packing her bags to head cross-country. Wilde and her rescue dog, Paco, jet-setted from sunny Los Angeles to the city that never sleeps. They moved in with Sudeikis in his New York City apartment. Things were definitely getting serious between these two.
Wilde told USA Today, "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. It's a good life." She went from working around the clock to preparing a home life for herself and her sweetheart. What was going to be next for this sweet couple?
As Beyoncé famously sang, "If you liked it, then you shoulda put a ring on it." So, after two years of dating, Sudeikis asked Wilde to marry her after the new year in 2012. He proposed with a vintage 1920s Parisian ring that had emeralds encircling a diamond. He liked it, so he put a ring on it!
As for the wedding details? During an interview with Marie Claire, Wilde said, "I don't know when we're going to get married, but it doesn't matter because we're going to be together forever. My dream is to have it close to New York. I love dressing up, and I want to design my own dress."
Becoming Drinking Buddies
First comes love, then comes engagement, and then comes... becoming drinking buddies together? Wilde was cast in Drinking Buddies, a comedy about two co-workers who realize they have feelings for each other when on a weekend trip with their partners. Sudeikis flew into Chicago to visit his fiancée while she was filming.
"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 an interview. Immediately, Sudeikis answered yes. So, the couple got to act and work together. Then, Sudeikis was off to film We're the Millers.
Say Hi to Otis
In October 2013, the couple had a big announcement for everyone, and it wasn't a wedding date. They were expecting their first child! A source close to the couple told PEOPLE, "They are incredibly happy. They're very excited to welcome a new member into their family."
On April 20, 2014, little Otis came into the world. Wilde announced his birth and name in a tweet. She wrote, "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I'm the building)." Apparently, Sudeikis isn't the only one in the family with comedy chops. The new parents were beyond excited for their new family.
The Biggest Commitment
The couple had a son together, but when would they tie the knot? They were madly in love with each other. Wilde spoke out on the subject in an interview with Glamour. "We're engaged, but no specific plans yet—we just have to find the time to put it together." Plus, they already had a family together
She continued, "In many ways, a child is more of a commitment. We are fully committed and really happy as a family." So, there was still no date for the big ceremony, but they had each other. They had their small family unit, which was about to gain another member.
Wilde and Sudeikis were soon expecting baby number two! In April 2016, she posted a photo on her Instagram with Otis and their "matching baby bumps." Then, on October 11, 2016, Wilde gave birth to their second child, a baby girl. The couple was overjoyed to welcome another kid into the world.
After being home from the hospital for a few days, Wilde posted a photo of the newborn on Instagram with the caption, "There goes the neighborhood. Daisy Josephine Sudeikis. Born, like a boss, on #internationaldayofthegirl." The mom of two added a small heart, too. Girl power!
With two children and busy work schedules, keeping the romance alive for Olivia and Jason must've been hard. However, they seemed to have no trouble with it. From posting cute photos on social media to constantly gushing about each other in interviews, these two lovebirds showed no signs of slowing down anytime soon.
How did they do it? Wilde told Us Weekly that the secret to the sauce is that "we prioritize date night." She continued, "We go out and have a lot of fun." Wilde and Sudeikis were up for anything from going to the movies or trying a new rollercoaster. But things were about to get that more interesting...
In the Director's Chair
The Life Itself actress was embarking on a new journey. She was stepping into the director's chair to direct her first feature-length film. While Wilde had dabbled in being behind the camera beforehand when she directed music videos for Edward Sharpe and the Magnetic Zeroes and the Red Hot Chili Peppers, this was a huge endeavor.
Booksmart starred Beanie Feldstein and Kaitlyn Dever as best friends who spent all of high school studying and began trying to make it up by partying for the first and last time. Sudeikis even showed up in the film with a small role as the school principal. It was an instant success - earning a gross of $25 million. Go, Olivia, Go!
The Bidding War
Following the success of her directorial debut with Booksmart, everyone wanted to be part of Wilde's second project. She was set to direct and star in a script from two writers called Don't Worry Darling. The psych thriller soon became part of a bidding war. Deadline reported that there were 18 different studios interested - from Netflix to MGM.
“I suddenly had the opportunity to make the decision of what would be the best home for us,” Wilde explained. Ultimately, Wilde chose New Line Cinema as the home of her second directorial feature. She later told Variety that she chose them because they were the only ones who promised a theatrical release.
Bye LaBeouf, Hello Harry
The cast for the project was announced to much excitement. Midsommar's Florence Pugh and Transformer's Shia LaBeouf were set to be the leads of the buzzy project. Pugh posted on her social media about how excited she was to be in the film. Then, seemingly out of nowhere, LaBeouf was out.
"I tried to mediate a situation between people to try to see if they could work together happily," Wilde recalled of his exit. "Once it became clear that it was not a tenable working relationship, I was given an ultimatum." And so, Harry Styles was hired instead. "We found the perfect Jack… it's kind of magical that it ended up being our first choice."
However, things back on the homefront were not going as magical. PEOPLE reported in November 2020 that Olivia Wilde and Jason Sudeikis had ended their relationship. After seven years of being engaged, they were calling it quits. Fans were left wondering how this could have even happened.
Sudeikis later came clean to GQ - and he was just as confused about the split: "I'll have a better understanding of why in a year," he said. "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."
Shortly after calling things off with Ted Lasso actor Jason Sudeikis, Wilde was spotted holding hands with the new star of her film, Harry Styles. In January 2021, they seemingly attended a wedding together, and according to Us Weekly, a source said that Styles called her his "girlfriend" during his speech. What was going on here?
Olivia Wilde was photographed at Styles' LA home. Meanwhile, a source close to the couple told PEOPLE that Sudeikis "was absolutely heartbroken about the split." The insider also mentioned that he had hoped they could repair things. Would they be able to mend their relationship? Or had Sudeikis officially gone out of style for Wilde?
That's a Wrap
The cast posed for a group photo to celebrate the end of filming. Everyone was all smiles, but that was only the beginning of the drama that was about to unfold. Wilde also dedicated a post to her new beau, writing that Styles "…infused every scene with a nuanced sense of humanity" - and that's only some of it.
Meanwhile, Sudeikis was also moving on with his life. PEOPLE reported that the actor was seeing British model Keeley Hazell. They initially met when Hazell had a small role in Horrible Bosses 2. Now, the former costars were becoming more than that. With a new movie coming out and her own budding romance, Wilde was also keeping busy.
You've Been Served
Things took a turn when Wilde attended CinemaCon in Vegas to promote Don't Worry Darling. She was speaking on stage when someone handed her a "Personal and Confidential" envelope. Joking it was "very mysterious," she opened it on the spot, thinking it might be a script. But upon opening the document, a stunned Wilde said, "Okay, got it. Thank you."
What happened? It turned out that the envelope contained custody papers regarding their 2 children. "It was my workplace... in any other workplace, it would be seen as an attack," she later told Variety. "It was really upsetting. It shouldn't have been able to happen. There was a huge breach in security, which is really scary. "
Stirring the Pot
Fans later began to speculate that something was up between Wilde and her film's lead when they noticed Pugh was not commenting on or liking a few of Wilde's posts about her or the movie. Plus, Page Six reported that Pugh was upset over Wilde's onset romance with Styles, with outlets reporting a big pay gap between the leads.
Wilde called these rumors "clickbait" in an interview with Variety. In the same interview, the director could not stop talking about how impressed she was with Pugh. Even though Wilde sidestepped answering anything directly about a feud with the Little Women actress, she mentioned that tabloids "pit women against one another..."
Shia Hits Back
The film's original actor, Shia LaBeouf, soon emerged from the woodwork. During the interview with Variety, Wilde mentioned that she had fired him to protect the energy and actors on set. Two days after her interview was published, LaBeouf spoke out. He wrote to Wilde and then forwarded those messages to Variety. Yikes.
LaBeouf wrote, "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." LaBeouf also sent a video of Wilde driving her car, asking LaBeouf to reconsider leaving the film and calling it "a wake-up call for Miss Flo." And that's not all.
In the midst of what was turning out to be a dramatic press tour for her film, Wilde still had to deal with what was happening at home with her children and ex-partner, Jason Sudeikis. After being served custody papers publicly, Wilde "was surprised and embarrassed," according to PEOPLE.
Since the envelope debacle, Wilde and Sudeikis were no longer on friendly terms. A source told PEOPLE, "She and Jason don't speak to each other, so they have help communicating about the custody schedule." Despite whatever the parents were reportedly arguing over, the same insider said Wilde "wanted to focus on what's best for the kids."
Don't Worry Darling had its world premiere at the iconic Venice Film Festival. However, one notable absence from the film's photocall and press was its lead actress Florence Pugh. One reporter asked about her absence, and Wilde said it was due to her prior filming obligations and refused to add to the "noise" of tabloid gossip.
Pugh was later present for a red carpet, and her stylist captioned an Instagram post of the actress with "Miss Flo." Clearly, she was referencing Wilde's video to LaBeouf. Fans also speculated that Styles spit on Chris Pine in what they dubbed #Spitgate. As they say in showbiz, the show must go on. So it did, despite the rumors.
"Our Relationship Was Over…"
In a September 2022 interview with Vanity Fair, Wilde addressed the rumors going around about her- and not those ones. She shared, "The complete horse**** idea that I left Jason for Harry is completely inaccurate." She added, "Our relationship was over long before I met Harry." So, what came crumbling down for them?
We may never know. Wilde also told Vanity Fair, "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. We were raising two kids during lockdown, so we co-parented through that time."
The Crew Speaks Out
Everyone was taking their turn to say something. Vulture published an article stating there was an explosive screaming match between Wilde and Pugh, and the director and Styles would disappear for stretches of time together. Enough was enough for the film's crew because they decided to intervene.
They released a statement to PEOPLE discrediting claims of any tension on set. They wrote, "Any allegations about unprofessional behavior on the set of Don't Worry Darling are completely false." They also spoke about Wilde and how she was "an incredible leader and director." We need a bag of popcorn...
Later in 2022, the custody battle that the two parents had been going through finally came to a close. The judge ruled in favor of Wilde, stating that the children's home was in Los Angeles, so the custody battle must continue in California. What would happen next for this family unit?
Sudeikis also expressed his regret and apologies for the papers being served while his ex-partner presented her film. He explained, "I did not want service to take place at the children's school because parents might be present," nor did he want them served at Styles' house in case his kids were there. But things weren't done yet.
The Nanny Diaries
Someone else was working through all this, and she had something to say. In October 2022, Sudeikis and Wilde's nanny, Ericka Genaro, spoke with the Daily Mail, spilling hot tea on what went down during the couple's split. She claimed that Sudeikis lay under Wilde's car when she was trying to leave to allegedly see Styles.
The nanny told Daily Mail that Sudeikis only found out about the full extent of Wilde's relationship with Styles after reading messages on an Apple Watch that she left behind. She also stated that one time she returned home to Sudeikis, "crying a lot, crying and crying." The nanny also shared screenshots of text messages in this fiery tell-all.
Sudeikis and Wilde quickly shut down any claims their former nanny had made. They released a joint statement, and they were not holding back. "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 continued, "Her now 18-month long campaign of harassing us, as well as loved ones, close friends, and colleagues, has reached its unfortunate apex." They were not going to back down. As for what is the actual truth, we may never know. But it isn't over yet...
As It Was
Throughout all the mayhem, Olivia and Harry were jet-setting around the world. Wilde supported her British heartthrob as he released his latest album, Harry's House. Fans were quick to point out lyrics that seemed to be about his lover, including one line that goes, "Leave America, two kids follow her."
Then, just like that, in November 2022, it was the end for the darling couple after almost two years of dating. Sources close to the pair told PEOPLE that Wilde and Styles were taking a break. He had his tour, and she had her kids and career to focus on. A source stated, "They're still very close friends."
The former couple was spotted hugging each other come January 2023. Would they be able to co-parent successfully and make amends? Only time will tell. For now, things reportedly seem to be amicable between the duo. Perhaps her recent breakup has something to do with it?
It seems like the answer is yes. A source close to Wilde told ET, "Olivia 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." The battle isn't finished yet, though. What happened next made our jaws drop.
As if everything the couple had gone through and is currently going through wasn't enough, their former nanny Ericka Genaro has hit Wilde and Sudeikis with a lawsuit. In February 2023, she filed a wrongful termination lawsuit at the Los Angeles Superior Court. Genaro is currently suing for a loss of earnings, medical expenses, and more.
She also claimed that after Wilde left their home, Sudeikis leaned on her more and more for support. The famous exes responded with the same statement they issued after her initial fiery interview. "We will continue to focus on raising and protecting our children with the sincere hope that she will now choose to leave our family alone," they shaded.
The saga is neverending. From an adorable Hollywood meet-cute to a tumultuous, public breakup, it has been a nonstop headline ride for Jason Sudeikis and Olivia Wilde these past few years. There are still so many twists and turns waiting to be unraveled.
Will they make amends and end up back together? What will happen with their lawsuit? Will Harry and Olivia find a way back to each other? There are so many unanswered questions, and only time can answer them. Stay tuned as the story continues to develop...