A Timeline Of Jason Sudeikis And Olivia Wilde's Relationship

Jason Sudeikis and Olivia Wilde's breakup broke hearts because fans love both actors. When the couple announced their breakup in November 2020, a source told People that "the split happened at the beginning of the year." The initial news from Wilde and Sudeikis was that they had been apart for most of 2020, and the decision appeared to be mutual. The couple share a son, Otis Alexander, 6, and a daughter, Daisy Josephine, 4.

In January 2021, photos of Wilde holding hands and getting cozy with Harry Styles made headlines, and the backstory about the celebrity couple's breakup was made public. Page Six reported that Wilde and Sudeikis broke up in early November 2020, and Harry Styles was supposedly the main reason for the split.

And in a July 2021 interview with GQ, Sudeikis revealed he's still processing the end of the relationship. Sudeikis said, "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." Sudeikis continued, "That's an experience that you either learn from or make excuses about. 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." Keep scrolling to learn more about the timeline of Sudeikis and Wilde's relationship.

Jason Sudeikis and Olivia Wilde's love story began in 2011

Per People, Jason Sudeikis and Olivia Wilde started dating in November 2011. It was fresh off of her split from former husband Tao Ruspoli (according to TMZ, she filed for divorce that March). The pair had an instant attraction to each other, first meeting at a "Saturday Night Live" after-party, but didn't act on their feelings for months. Around six months later, they started officially dating.

In a 2013 interview with Allure, Wilde revealed that she was attracted to Sudeikis the moment she met him, but "he didn't even get my number." The "Booksmart" director told the outlet that they kept running into each other until, finally, one of her friends intervened. Wilde said, "[One night] my best guy friend walked up to him and said, 'This is Olivia's number. Use it.' That was the beginning" (via Us Weekly).

In 2017, Sudeikis told Stephen Colbert on "The Late Show" (via People) about the night he met Wilde. The "Horrible Bosses" star confessed he didn't pursue Wilde when they first met because he heard she was dating someone. After the couple kept running into each other, Sudeikis explained to Colbert, "The universe had more in store for us in the fall."

The couple got engaged about a year into dating

It's true what they say: when you know, you know. It didn't take long for Jason Sudeikis and Olivia Wilde to make things ultra-official — and for Christmas in 2012, Wilde got an engagement ring. Okay, it wasn't exactly Christmas, but according to People, the "SNL" star proposed to the former "House" actor right after the holidays in 2012. They had been dating for about a year.

Wilde first denied the engagement rumors. In December, the star tweeted, "No I'm not engaged but I AM at the Stones show and holy s*** Ronnie Wood you got style, boy. It's just a fact. Trying to score a shoe pic." Apparently, she has a thing for rockers, which we'll get to later. Little did she know (or maybe she did) that Sudeikis was about to get down on one knee.

Sudeikis ultimately chose a unique engagement ring for Wilde. As reported by Glamour, a halo of emeralds surrounded the large center diamond, which was set on a thin, gold band. It was a little bit vintage and a little bit unique — just like Wilde and their non-traditional engagement to come.

In 2014, Olivia Wilde had their son, Otis

In 2013, Jason Sudeikis and Olivia Wilde appeared in their first rom-com together. Wilde starred as Kate, while her "SNL" beau made an appearance as Gene. According to WWD, at the premiere, the star donned a sapphire J. Medel dress — but her red carpet looks were about to drastically change. Little did fans know, Wilde would soon need to accommodate a baby bump.

In October 2013, E! News confirmed that the couple was expecting their first child together. From there, Wilde showed off her baby bump on red carpets galore, including at the 2014 Academy Awards. Meanwhile, Sudeikis gushed about his bride-to-be, telling Modern Luxury Manhattan (via E! News) "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."

In April 2014, Wilde went into labor during a concert at NYC's Webster Hall. As she revealed in an Instagram post, her water broke right on the balcony. She gave birth to their son, Otis Alexander Sudeikis, not long after.

The pair welcomed their daughter, Daisy, in 2016

Four years into their engagement, Olivia Wilde and Jason Sudeikis still hadn't picked a wedding date. It seemed like the pair wasn't in any rush to get married. During an April 2016 appearance on "Watch What Happens Live," the "SNL" comedian joked that they wouldn't tie the knot until weed was federally legalized. Days after the episode, Wilde revealed that she was expecting their second child. The star posted a cute snap of her baby bump on Instagram, and later that year, she told Yahoo! Beauty about her plans to raise children with feminist values.

"I want to promote the idea that the definition of feminism is equality, and it's something that's not difficult to teach children because they are born with that sensibility," she said. "They are only taught to separate people and value them differently once they get older."

According to People, the couple welcomed Daisy Josephine Sudeikis in October. In an Instagram post, Wilde revealed that her daughter was "Born, like a boss" on International Day of the Girl.

Wilde and Sudeikis called it quits in 2020

Juggling two successful Hollywood careers while raising two small children likely put pressure on Jason Sudeikis and Olivia Wilde. In February 2020, Page Six reported that while Wilde won an Indie Spirit Award for directing "Booksmart" in L.A., Sudeikis was in New York partying with friends from "Saturday Night Live." Their jobs often brought them to separate cities, so it wasn't abnormal, but a source later told People that the couple officially called it quits at the start of the year.

Only Sudeikis and Wilde know what happened between them, but some reports say Wilde's relationship with Harry Styles began as early as October 2020. The star has denied all allegations of cheating, laying out a timeline of her relationship with the rocker in her September 2022 Vanity Fair cover story. Nonetheless, tabloids like the Daily Star claimed Sudeikis didn't see Wilde's relationship with the British singer coming.

In interviews, it seems like Sudeikis takes responsibility for his actions. Most importantly, the "Ted Lasso" star is moving forward with his life and realizing the good that comes after heartbreak. In his July 2021 interview with GQ, Sudeikis said, "I think if you have the opportunity to hit a rock bottom, however you define that, you can become 412 bones or you can land like an Avenger. I personally have chosen to land like an Avenger."

Cue: A nasty custody battle

After their split, Olivia Wilde and Jason Sudeikis worked together to co-parent their kids. At the beginning, it was reportedly smooth-sailing. A source told People that Sudeikis hoped to repair their relationship, but the children were their priority. "It's been amicable and they've transitioned into a great co-parenting routine," the source revealed. In public, both partners appeared to move on. Wilde was officially dating Harry Styles. Sudeikis was romantically linked to English actor Keeley Hazell (though the couple would eventually split about a year later, according to Us Weekly). Then, the cracks started to show.

According to the Daily Mail, things became unsustainable when the pair — who split time between New York, London, and Los Angeles — began arguing about where they would permanently raise their children. Per Us Weekly, Sudeikis ultimately served Wilde custody papers while she was speaking on a panel at CinemaCon. It was a small drop in a bucket of drama surrounding "Don't Worry Darling."

In a petition to dismiss, which was obtained by the Daily Mail, Wilde alleged that Sudeikis served her publicly in an attempt to professionally embarrass her. According to People, a judge ultimately sided with Wilde, dismissing Sudeikis' motion — but things are far from over. At the time of this writing, they're reportedly no longer speaking, unless it's through a third party.

The nanny spoke to the press, and it wasn't pretty

If there was one thing that united Jason Sudeikis and Olivia Wilde, it was disputing their former nanny's salacious claims. In October 2022, the childcare worker came forward in a bombshell Daily Mail report that detailed the couple's supposedly turbulent engagement — and she brought alleged text message receipts. Buckle up because it's even worse than Wilde's now-infamous "Miss Flo" moment.

Per the Daily Mail, the nanny claimed that Wilde went from sharing wedding plans to living in a hotel after falling for Styles on the set of "Don't Worry Darling." Sudeikis reportedly had an over-the-top reaction to their breakup that involved near-constant crying. It only got worse when he allegedly discovered incriminating text messages on Wilde's Apple Watch and banned the nanny from playing the rocker's music around his kids. Things allegedly came to a head over a salad with "special dressing" — the contents of which remain unknown. The nanny claimed Wilde prepared the salad for Styles in the family kitchen, and Sudeikis allegedly launched into a rage, lying down beneath her car to prevent her from leaving to meet him.

In a joint statement, Wilde and Sudeikis told the Daily Mail that the nanny was a jilted former employee. "Her now 18 month long campaign of harassing us, as well as loved ones, close friends, and colleagues, has reached its unfortunate apex," they said. Nothing brings a Hollywood family together like having to refute a dramatic tabloid report.