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Jason Sudeikis and Olivia Wilde ended their relationship in 2020 after a seven-year engagement
News of the couple's split first broke in November 2020, when PEOPLE exclusively reported that 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.
Days after PEOPLE reported their breakup, Sudeikis and Wilde were spotted hugging in Los Angeles, and the exes continued to support each other's respective projects. Sudeikis thanked Wilde in his acceptance speech after his hit Apple TV+ comedy series, Ted Lasso, swept the Critics Choice Awards, while Wilde congratulated him on the win via Twitter.
That's not to say there haven't been a few bumps along the way, however. In April 2022, Wilde, who is currently dating Harry Styles, was served with legal papers concerning their son, Otis, 8, and daughter, Daisy, 5, while onstage at CinemaCon in Las Vegas.
A source told PEOPLE that the Ted Lasso star, who was last linked to British model Keeley Hazell in November 2021, "had no prior knowledge of the time or place that the envelope would have been delivered."
From their SNL meet-cute to their seven-year engagement, here's a complete timeline of Jason Sudeikis and Olivia Wilde's relationship.
May 2011: Jason Sudeikis and Olivia Wilde meet at a Saturday Night Live finale party
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.
Instead, he got deep. "I was just learning to be by myself. We were both seeing people but were single," Wilde previously told Marie Claire. "He seemed to really see me, see through the bulls––t."
The actress revealed even more about the pair's first introduction in a 2016 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 told Allure. "[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,' " Wilde later told Howard Stern, adding, "I was on the hook."
So surprised was the Tron star by his restraint, in fact, that she joked she became concerned for his wellbeing. "I was like, 'You guys, did Jason Sudeikis die, because I don't have any texts.' "
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 on The Late Show With Stephen Colbert. "So I didn't make any moves. I was just very, very busy 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
Wilde later revealed to Marie Clarie that 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 told Marie 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 literally didn'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
The pair sat side-by-side and sported matching University of Kansas Jayhawks hats while attending the team's baseball game in December 2011. At the time, reps for both actors had no comment about their rumored romance.
October 2012: Olivia Wilde reveals she's living with Jason Sudeikis
In an October 2012 interview with USA 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
Wilde opened up about her feelings for her boyfriend during a monologue reading hosted by Glamour magazine in October 2012. Though she didn't mention the Masterminds star directly, she told the audience that she was "blissfully, hopelessly, wildly in love," adding, "We hold hands. I never f—— hold hands."
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
The Horrible Bosses star popped the question to Wilde with a 1920s Parisian engagement ring that featured a circle of emeralds around a center diamond — one that Wilde told Marie Claire Sudeikis 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 about her dreams for motherhood to Marie Claire in 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
After the actor lost a considerable amount of weight in 2013, Sudeikis said he had love to thank for his new healthy lifestyle.
"Being happy, and in love, for me, was the secret," he told Modern Luxury Manhattan in 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 in Drinking 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," Wilde revealed to ABC News. "He didn't know he was gonna have to work, he came to visit me in Chicago before he went to shoot We'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 couple confirmed to PEOPLE exclusively in 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
Six months later, their son was born on April 20, 2014.
Wilde shared the good news — along with the baby's name — on Twitter several days after his birth. "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I'm the building)," she wrote alongside a sweet black-and-white photo of her and the newborn.
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" while speaking to Glamour in 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 an adoring message for 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 Sudeikis are "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 a cover story for Net-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 while speaking to PEOPLE at 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
Just days later, the Life Itself actress revealed that she'd be getting her wish sooner than expected, as she was already expecting. Posting a photo of herself and her son Otis smiling at each other while holding their stomachs, Wilde wrote, "Matching baby bumps."
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 the arrival of their daughter, Daisy Josephine. Wilde shared the first photo of the newborn a few days later with a sweet Instagram shot of 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 an Instagram photo of 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
Wilde chatted with PEOPLE about 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
PEOPLE reported in 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 were spotted sharing a hug in L.A. on November 17, 2020.
January 2021: Olivia Wilde is seen holding hands with Harry Styles
In early 2021, Wilde was spotted holding hands with Harry Styles at a wedding.
A source told PEOPLE that the pair, who met on the set of Wilde's film Don't Worry Darling, were still early on in their 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, a source revealed to PEOPLE that 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
A source shared with PEOPLE in 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 in Horrible Bosses 2 together, "knew each other from many years ago."
March 2021: Jason Sudeikis credits Olivia Wilde with the idea for turning Ted Lasso into a show
After winning the Critics Choice Award for best comedy series for Ted Lasso, Sudeikis thanked his ex-fiancée during his virtual acceptance speech.
"I want to thank [my kids'] mom Olivia, who had the initial idea to do this as a TV show, saying, 'You and Brendan [Hunt] and Joe [Kelly] like doing that so much, you should do it as a movie or TV show,' " he said.
The actress also made a joke about Sudeikis' ultra-comfy choice of wardrobe for 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 an interview with GQ in 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, a source told PEOPLE in 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
Wilde was served with legal documents regarding 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.
An industry source later told PEOPLE that while Wilde "was surprised and embarrassed" by the ordeal, she "moved forward with little fuss."
"Olivia was professional and adult about what happened and made sure the show went on," the insider added.
Another source told PEOPLE that 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.
August 2022: Olivia Wilde claims Jason Sudeikis meant to "embarrass" her by serving custody papers onstage
In court documents obtained by the Daily Mail, the actress and director accused Sudeikis of "embarrass(ing) me professionally" and said his method of delivery was "aggressive."
"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."
According to court documents obtained by PEOPLE on August 10, a New York judge granted Wilde's motion to dismiss Sudeikis' petition on the grounds that the state does not have jurisdiction over the children's custody petitions. "New York is not the home state of the subject children," the documents read. The custody case will stay in California.
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 source told PEOPLE that 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 to Variety about being served custody papers from 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 for Vanity Fair, Wilde addressed the rumors that 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 to not, 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 on The 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."
The Don't Worry Darling director 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."
October 17, 2022: Olivia Wilde and Jason Sudeikis deny "false and scurrilous" statements by former nanny
During an interview with the Daily Mail, a former nanny shared alleged details of the days following Wilde and Sudeikis' split. The exes responded 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 the Ted Lasso star 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 Sudeikis sharing a hug after 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."
The most recent filing by Sudeikis' team was a request for the custody matter to be settled in an N.Y.C. court instead of in Los Angeles, where the case is currently underway. The request was ultimately denied.
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