Olivia Wilde and Jason Sudeikis.Photo: Jamie McCarthy/Getty Images
Jason SudeikisandOlivia Wildeare navigating their new relationship as co-parents.
News of the couple’s split first broke in November 2020, whenPEOPLE exclusively reportedthat Sudeikis and Wilde had ended their engagement of seven years.
“The children are the priority and the heart of the family’s relationship,” a source told PEOPLE at the time, adding that the pair, who share two children together, had broken up at the beginning of 2020.
That’s not to say there haven’t been a few bumps along the way, however. In April 2022, Wilde, who is currentlydating Harry Styles, wasserved with legal papersconcerning their son, Otis, 8, and daughter, Daisy, 5, while onstage at CinemaCon in Las Vegas.
A source told PEOPLE that theTed Lassostar, who waslast linked to British model Keeley Hazellin November 2021, “had no prior knowledge of the time or place that the envelope would have been delivered.”
From theirSNLmeet-cute to their seven-year engagement, here’s a complete timeline of Jason Sudeikis and Olivia Wilde’s relationship.
Olivia Wilde (L); Jason Sudeikis.Gabe Ginsberg/WireImage; Rich Fury/Getty
May 2011: Jason Sudeikis and Olivia Wilde meet at aSaturday Night Livefinale party
Sparks first flew for Sudeikis and Wilde on the set ofSaturday Night Live. “I met her at a finale party forSNL,” Sudeikistold Stephen Colbertin 2017, adding, “We hit it off that night.”
According to Wilde, who later opened up to Allure about their first meeting, it was Sudeikis' moves on the dance floor that helped put him on her radar. “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,” she told the outlet.
The actress revealed even more about the pair’s first introduction in a2016 interview with Howard Stern.
“He came up to me and he said, ‘Whatever you’re looking for, you don’t need it,’ " she recalled. “And he walked away.”
After Sudeikis failed to get her number, Wilde decided to take matters into her own hands.
“Over the next six months we kept running into each other,” she toldAllure. “[One night], my best guy friend walked up to him and said, ‘This is Olivia’s number. Use it.’ That was the beginning.”
2011: Jason Sudeikis first texts Olivia Wilde
One month after getting Wilde’s number from her friend, Sudeikis finally reached out to the actress. “When he got my number, he didn’t text me for a month. I was like, ‘This is incredible,’ " Wildelater told Howard Stern, adding, “I was on the hook.”
According to Sudeikis, the truth was far more tame. “I actually came off looking a little cooler than I really am because I had heard through the grapevine, through mutual friends who weren’t exactly her best girlfriends, who would report back, ‘Oh you know, I think she’s dating someone,’ " he said during an appearance onThe Late Show With Stephen Colbert. “So I didn’t make any moves. I was just very,verybusy with other things. And next thing you know, I stopped being busy, she stopped dating someone, and then it was off to the races.”
2011: Jason Sudeikis and Olivia Wilde go on their first date
Jason Sudeikis and Olivia Wilde.Suzanne Cordeiro/Shutterstock
Wilde laterrevealed toMarie Clariethat she had insecurities about meeting up with the actor on their first date.
“I thought, ‘He won’t be interested in me; I’m not a contender,’ " she said. “He was so cool, so funny—I was such a fan of his and had always fancied his speed and his intelligence. He’s a brilliant actor with a brain like lightning.”
The director said she even questioned whether Sudeikis would be attracted to her physically, saying, “I thought, ‘I’m not beautiful enough or his type.’ I couldn’t wait to sit down and hear him talk.”
When they did finally share an evening of conversation, Wilde said that they “closed down the [New York City] restaurant at 2 a.m.”
At the end of the night, the comedian didn’t try to kiss her — a gesture Wilde found to be gallant. “He was never overly flirtatious,” she toldMarie Claire. “He had patience and sincerity and kindness. No presumptuousness.”
She added: “I was madly in love. I was overwhelmed.”
2011: Jason Sudeikis kisses Olivia Wilde
Wilde detailed the timeline of the couple’s first kiss during a March 2016 interview with Howard Stern. “He literallydidn’t kiss me until the fourth date,” she said. “He finally kissed me. And I was like, completely head over heels.”
Still, she said she managed to maintain some mystery of her own, departing before things could go any further. “I’m a lady. So I left. I was like, ‘Got the kiss, I gotta leave now.’ "
December 2011: Jason Sudeikis and Olivia Wilde are spotted together at a sporting event
October 2012: Olivia Wilde reveals she’s living with Jason Sudeikis
In an October 2012interview withUSA TODAY, Wilde revealed that she was living with Sudeikis and her rescue dog Paco in New York City. “I’ve been decorating our new apartment. That’s a lot of what I do,” she told the publication, adding, “I’m so domestic.”
October 2012: Olivia Wilde says she’s “wildly in love” with Jason Sudeikis
John Shearer/Getty Images
She also spoke out about their physical activity, comparing their bedroom antics to “Kenyan marathon runners.”
October 2012: Jason Sudeikis and Olivia Wilde are seen kissing in Rome
Later that month, the couple was seen kissing while abroad in Rome. Wilde, who was on location for her latest film,The Third Person, enjoyed a two-person rickshaw bike ride with the actor, as well as a romantic dinner at La Taverna degli Amici, where they shared a bottle of wine.
January 2013: Jason Sudeikis proposes to Olivia Wilde
TheHorrible Bossesstarpopped the questionto Wilde with a 1920s Parisian engagement ring that featured a circle of emeralds around a center diamond — one that Wilde toldMarie ClaireSudeikis had been carrying around for a month. “They are so excited,” a source told PEOPLE at the time. “And very, very happy.”
April 2013: Olivia Wilde says she wants three kids with Jason Sudeikis
Wilde opened up abouther dreams for motherhoodtoMarie Clairein 2013. “We’ve discussed all our ideals and hopes. I can’t wait for children,” she said. “I’m open-minded about how many, but three, which I love, is like a little party.”
The actress also noted that she wasn’t in any rush to start a family, however. “I am not trying to have kids now,” she clarified. “There’s no strict plan for anything in my life. What happens, happens.”
Still, she couldn’t help but imagine Sudeikis as a dad. “He’s so good with kids. I’ve never before experienced looking at someone and thinking, ‘That’s who I want to raise a child with.’ "
July 2013: Jason Sudeikis credits Olivia Wilde for his newfound health
Axelle/Bauer-Griffin/FilmMagic
After the actor lost a considerable amount of weight in 2013, Sudeikissaid he had love to thankfor his new healthy lifestyle.
“Being happy, and in love, for me, was the secret,” he toldModern Luxury Manhattanin July 2013. “I feel like I returned home to myself as an individual through the process of falling in love with the sweetest woman I’ve ever known.”
August 2013: Jason Sudeikis and Olivia Wilde costar inDrinking Buddies
Sudeikis shared his comedic talent with Wilde for her 2013 film,Drinking Buddies. As it turns out, his appearance was completely unplanned.
“We roped him in,” Wilderevealed toABC News. “He didn’t know he was gonna have to work, he came to visit me in Chicago before he went to shootWe’re the Millers,and 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?’ " she recalled. “And he’s like, ‘Yeah, great, let’s go.’ "
Wilde said watching her fiancé work was “a delight,” adding, “I’m just trying not to laugh the whole time, ‘cause he just makes me and everyone else laugh so hard. He’s just, so good.”
October 2013: Jason Sudeikis and Olivia Wilde confirm they’re expecting their first child
Reps for the coupleconfirmed to PEOPLE exclusivelyin October 2013 that the pair would soon be parents. “They are incredibly happy,” a source shared. “They’re very excited to welcome a new member into their family.”
April 2014: Jason Sudeikis and Olivia Wilde welcome a son
Source: Olivia Wilde Instagram
Six months later, theirson was bornon April 20, 2014.
September 2014: Olivia Wilde gives an update on her marriage plans with Jason Sudeikis
Wilde revealed that the duo still weren’t quite ready to say their “I dos” whilespeaking toGlamourin 2014. “We’re engaged, but no specific plans yet — we just have to find the time to put it together,” she said.
Still, the actress said she was in no rush. “In many ways, a child is more of a commitment. We are fully committed and really happy as a family,” she shared. “And there’s no definition of the ‘normal family’ anymore. Kids today are growing up with so many different definitions of family. I guess what I’m saying is that I don’t feel any pressure to do it. But I think it will be really fun.”
September 2015: Olivia Wilde wishes Jason Sudeikis a happy 40th birthday
Wilde had anadoring messagefor her fiancé on his milestone birthday, posting a cute photo of herself kissing his cheek and writing, “Happy Birthday to the loveliest man I’ve ever known. 40 years of you has made the world a better, funnier place.”
February 2016: Olivia Wilde says she and Jason Sudeikisare “committed”
Two years later, the pair were seemingly no closer to walking down the aisle, despite being as unified as ever.
“We are seriously connected,” Wilde said in acover story forNet-a-Porter. “Before you have a child, marriage is the ultimate commitment and promise to one another, and then once you have a child, it’s like, ‘Oh, we’re committed and promised already.’ "
April 2016: Olivia Wilde says she’s “desperate” for more kids with Jason Sudeikis
Wilde hinted that she may not be done having children whilespeaking to PEOPLEat a Marimekko for Target event in N.Y.C. in December 2020. “I’m desperate for more [kids]!” she said.
As for how many she’d like, Wilde left the possibilities open, saying, “I love my siblings so much and Jason has incredible siblings too. The more the merrier.”
April 2016: Olivia Wilde announces she is pregnant
October 2016: Olivia Wilde gives birth to her and Jason Sudeikis’ second child
The couple’s family expanded once more on October 11, 2016, with thearrival of their daughter, Daisy Josephine. Wilde shared the first photo of the newborn a few days later with a sweetInstagram shotof her laying on an oversized sheep. “There goes the neighborhood,” she wrote, adding, “Born, like a boss, on#internationaldayofthegirl. ❤️”
July 2017: Olivia Wilde says she’s still “crushing” on Jason Sudeikis
After six years together and two children, Wilde revealed that she was still crazy for her fiancé, captioning an adorable photo of the pair snuggled up together with the word, “crushing.”
July 2017: Jason Sudeikis and Olivia Wilde adopt a dog together
Wilde introduced the world to her family’s newest member in July 2017 with anInstagram photoof their new rescue dog, Elvis Sudeikis-Wilde.
“Ladies and gentlemen, meet the heartbreaker formerly known as Maxamillion,” she captioned the snap, adding that the pup was the “missing member of our brood.”
April 2019: Olivia Wilde opens up about directing Jason Sudeikis
Wildechatted with PEOPLEabout her experience directing Sudeikis on the set of her 2019 film,Booksmart. “He’s one of the best improvisers in the world, so I knew I could cast him,” she shared. “He’s like spinning a top and just letting it roll. It’s really amazing to see him do his thing.”
November 2020: PEOPLE reports that Jason Sudeikis and Olivia Wilde ended their engagement
Jason Sudeikis (L); Olivia Wilde.Jeff Kravitz/FilmMagic; Getty
PEOPLE reportedin November 2020 that the couple had called it quits on their relationship and ended their engagement of more than seven years.
“It’s been amicable and they’ve transitioned into a great co-parenting routine,” a source said of their split. “The children are the priority and the heart of the family’s relationship.”
November 2020:Jason Sudeikis and Olivia Wilde share a hug in L.A.
The exes appeared to be on friendly terms despite their recent split when they werespotted sharing a hugin L.A. on November 17, 2020.
January 2021: Olivia Wilde is seen holding hands with Harry Styles
In early 2021, Wilde wasspotted holding handswith Harry Styles at a wedding.
A source told PEOPLE that the pair, who met on the set ofWilde’s filmDon’t Worry Darling, were still early on intheir romance. “They have dated for a few weeks,” the source said. “They were affectionate around their friends, held hands and looked very happy.”
January 2021: A source says Jason Sudeikis is “heartbroken” over his split from Olivia Wilde
That same month, asource revealed to PEOPLEthat Sudeikis was still “absolutely heartbroken” over his breakup with Wilde. “There is still a lot of love there, and he would like to have hope that maybe there’s a way for them to repair things,” the insider said.
February 2021: Jason Sudeikis begins casually dating Keeley Hazell
Asource shared with PEOPLEin February 2021 that Sudeikis was spending time with British model Keeley Hazell, though he wasn’t seeking anything serious. The source also noted that the two, who costarred inHorrible Bosses 2together, “knew each other from many years ago.”
March 2021: Jason Sudeikis credits Olivia Wilde with the idea for turningTed Lassointo a show
Christopher Polk/NBC/NBCU Photo Bank via Getty Images
After winning the Critics Choice Award for best comedy series forTed Lasso, Sudeikis thanked his ex-fiancée during hisvirtual acceptance speech.
Shortly after, Wildecongratulated Sudeikisand the show’s cast for their Critics Choice Awards wins onTwitter.
The actress also made a joke about Sudeikis' ultra-comfychoice of wardrobefor his acceptance speech, writing, “I hope this means we all keep wearing hoodies when the ceremonies are in person next year.”
July 2021: Jason Sudeikis breaks his silence on his split from Olivia Wilde
Jason Sudeikis commented on his high-profile split for the first time during aninterview withGQin July 2021. “I’ll have a better understanding of why in a year, 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,” he told the publication.
In the meantime, Sudeikis said he was keen on learning what he could from their breakup.
“That’s an experience that you either learn from or make excuses about,” he said. “You take some responsibility for it, hold yourself accountable for what you do, but then also endeavor to learn something beyond the obvious from it.”
November 2021: Jason Sudeikis starts “casually seeing” Keeley Hazell again
After a brief cooling off period, asource told PEOPLEin November 2021 that Sudeikis and Hazell were spending time together again. “They’re casually seeing each other again,” the source said. “It’s never been a serious thing. They’re just enjoying each other’s company.”
April 2022: Olivia Wilde is served with legal papers from Jason Sudeikis at CinemaCon
Olivia Wilde.Frazer Harrison/Getty
Wilde wasserved with legal documentsregarding the former couple’s children while onstage at CinemaCon in Las Vegas, Nevada. “Papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” a source explained to PEOPLE.
The actress was given an envelope marked “Personal and Confidential” mid-presentation. After opening it, she acknowledged receipt of the papers with a simple, “Okay, thank you,” before continuing to speak about her film,Don’t Worry Darling.
“Olivia was professional and adult about what happened and made sure the show went on,” the insider added.
Anothersource told PEOPLEthat Sudeikis “had no prior knowledge” of when the papers would be delivered, as the manner would “solely be up to the process service company involved and he would never condone her being served in such an inappropriate manner.”
Family law attorney David Glass, however, said that it’s “highly unlikely” that Sudeikis would be unaware of these details. Glass, who is not involved with Sudeikis and Wilde’s case, noted to PEOPLE that he talks to each of his clients before serving a party to get information on where they can be served.
“If you’re going to go to that sort of extreme length to do it publicly, to do it in an embarrassing way, I can’t see the client not knowing about it. You’re obligated as an attorney to share most things that you’re doing with your client,” he said.
A few months after she wasserved custody papersduring a presentation onstage, Wildefiled to dismissSudeikis' New York petition for custody of their two children.
“Jason’s actions were clearly intended to threaten me and catch me off guard. He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible,” Wilde said in her court filing.
In his own filing, Sudeikis reiterated that he did not intend for Wilde to receive the papers onstage, and had instead requested that they be served at Heathrow Airport. He also explained of Wilde, “I did not want service to take place at the home of Olivia’s current partner because Otis and Daisy might be present.”
August 17, 2022: A source says Olivia Wilde and Jason Sudeikis “don’t speak” but want “what’s best for the kids”
In the midst of Sudeikis and Wilde’s contentious custody battle, a sourcetold PEOPLEthat Wilde “wants to focus on what’s best for the kids.”
“She and Jason don’t speak to each other, so they have help communicating about the custody schedule,” the insider added.
The source also said that though Wilde is “upset about the custody drama,” she still “wants the kids to see” their father “as much as possible.”
“She hopes they can figure out the best living situation for everyone,” the source said.
August 24, 2022: Olivia Wilde opens up about being served custody papers from Jason Sudeikis onstage
Wilde talked toVarietyabout being servedcustody papersfrom Sudeikis onstage during a CinemaCon presentation, saying she “hated that this nastiness distracted from the work of so many different people and the studio that I was up there representing.”
“To try to sabotage that was really vicious,” added Wilde. “But I had a job to do; I’m not easily distracted. … But, you know, sadly, it was not something that was entirely surprising to me. I mean, there’s a reason I left that relationship.”
Meanwhile, a source close to Sudeikis told PEOPLE, “This was obviously someone’s big mistake and Jason was really upset. Jason didn’t want that.”
“The process server chose where to do it that way and it was messed up,” the insider added. “But no one would have ever known she was served onstage if someone close to her hadn’t revealed what was in the envelope, because people thought it was a script.”
September 8, 2022: Olivia Wilde denies leaving Jason Sudeikis for Harry Styles
In a cover story forVanity Fair, Wildeaddressed the rumorsthat she left Sudeikis for Styles. “The complete horses— idea that I left Jason for Harry is completely inaccurate,” Wilde said. “Our relationship was over long before I met Harry.”
“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 [COVID-19] pandemic,” she continued. “We were raising two kids during lockdown, so we co-parented through that time.”
Wilde added, “Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing tonot,because we could be better parents as friends who live in different houses.”
September 21, 2022: Olivia Wilde says kids' happiness remains top priority for her and Jason Sudeikis
During an appearance onThe Kelly Clarkson Show, Wilde talked about the ups and downs of becoming a single parent.
“Reshaping a family is tricky,” she said. “One benefit is that it’s allowed for some really deep conversations with my kids, like about emotions and about happiness. It’s actually allowed me to get to know them in a different way.”
TheDon’t Worry Darlingdirector went on to say that her kids remain her top priority.
“My ex and I agree on that, they are everything to us,” Wilde said. “There are so many families who are blended. But, you know, it’s tricky because we’re not doing it in private.”
During an interview with theDaily Mail, a former nanny shared alleged details of the days following Wilde and Sudeikis' split. The exesresponded to the claims in a joint statement.
“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,” the former couple said. “Her now 18 month long campaign of harassing us, as well as loved ones, close friends and colleagues, has reached its unfortunate apex. 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.”
The nanny claimed that Sudeikis was “brokenhearted” when Wilde began dating Styles.
“On the Monday morning [of] Nov. 9, when I came back from a weekend off, [Jason] was crying a lot, crying and crying. I didn’t know what had happened at all,” the nanny told the outlet. “After I’d got the kids ready, Jason came upstairs and was having some coffee. He was crying and a mess, saying, ‘She left us. She left us!’ "
The unnamed nanny also said that they saw Sudeikis lie down under Wilde’s car to prevent her from leaving the house to see Styles. They also claimed that theTed Lassostar banned his kids from playing Styles' music.
January 27, 2023: Olivia Wilde and Jason Sudeikis share a hug while out in Los Angeles
Photographers captured Wilde and Sudeikissharing a hugafter what appeared to be a relaxed conversation between parents. Both actors were casually clad — Wilde wore a yellow sweatshirt and jeans, while Sudeikis donned a hoodie and slacks.
March 24, 2023: Olivia Wilde’s lawyers say Jason Sudeikis is trying to “litigate her into debt”
Wilde and Sudeikis continue to be in disagreement about whether their kids should live in Los Angeles or New York City.
In the latest court filings, Wilde’s legal team stated that Sudeikis is trying to “litigate her into debt” and is acting “in bad faith.”
The lawyers added: “While Jason can afford to spin his wheels with filing after filing, Olivia cannot. Jason seems intent on throwing whatever he can against the wall to see what will stick.”
source: people.com
