Olivia Wilde and Jason Sudeikis: A Timeline of Their Relationship

Wilde and Sudeikis met in 2011 following their respective divorces. The Booksmart director was married to Italian-American filmmaker Tao Ruspoli from 2003 to 2011, while the Saturday Night Live alum was married to screenwriter and filmmaker Kay Cannon from 2004 to 2010. During a 2017 appearance on The Late Late Show With Stephen Colbert, the Horrible Bosses star dished on his first interaction with Wilde. “I actually came off looking a lot cooler than I really am because I had heard through the grapevine, through mutual friends that weren’t exactly her best girlfriends, that would report back, ‘Oh, you know, I think she’s dating someone,’ so I didn’t make any sort of moves,” he recalled at the time. “I was just very, very busy with other things.” [sendtonews type="float" key="cWj5F7Ntu8-2840849-14453"] The former House actress, for her part, opened up how her separation from Ruspoli led her to Sudeikis in Marie Claire’s April 2013 cover story. “I had grown up with Tao; we had just drifted. I felt I had something to prove,” she explained at the time. “If you fall off a horse, you get back up. I am not a quitter. I hung on for as long as possible, until it was more hurtful to stay.” Wilde continued, “I’m so grateful for the pain and the heartbreak. It gave me the courage to leave and brought me to the great love of my life.” The Tron: Legacy star also told the publication that she wasn’t necessarily looking for love when she first met Sudeikis, adding, “I was just learning to be by myself; I’d been divorced nine months. We were both seeing people but were single. He seemed to really see me, see through the bulls--t.” Wilde and Sudeikis announced their engagement in 2013. They are now parents of son Otis and daughter Daisy. Speaking to Net-a-Porter’s Porter Edit in February 2016, Wilde explained how she believed becoming a parent alongside Sudeikis was a stronger commitment for the couple than tying the knot. “We are seriously connected,” she said. “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.’” Us Weekly confirmed in November 2020 that the longtime couple’s romance came to an end.

Wilde first met Sudeikis while attending a Saturday Night Live wrap party following the sketch comedy show’s season 36 finale.

The acting duo struck up a romantic relationship six months after meeting.

It was announced that Sudeikis proposed to Wilde after two year years of dating.

Sudeikis appeared in Wilde’s indie movie Drinking Buddies.

Wilde was pregnant with the engaged couple’s first child.

The Butter actress gave birth to the duo’s first child, Otis.

Wilde posted a candid photo to Instagram of the couple kissing, writing, “Best part of a great night. ❤️.”

During an appearance on Watch What Happens Live With Andy Cohen, Sudeikis joked about when he would eventually marry Wilde. “I know this isn’t my mom because my mom’s in the audience,” the Kansas native joked at the time while responding to a caller’s question. “I mean, I believe we won’t get married until weed is legal in every state.”

Wilde confirmed she’s pregnant with the couple’s second child in the cutest way, sharing a photo of herself and Otis — who was nearly 2 at the time — holding their bellies. “Matching baby bumps,” she wrote via Instagram at the time.

The couple welcomed their second child together, Daisy.

Wilde posted a sweet photo of the longtime couple staring into one another’s eyes. “#❤,” she wrote that Valentine’s Day.

Wilde honored Sudeikis with a sweet tribute on his 42nd birthday. “I have approximately one billion pictures of this guy, my partner in life-crime, who was born on this day in 1975, but this one represents his latest chapter, the one in which he became a dad to a little woman, who will grow up thinking all men can dance, sink a jump shot, and tell great jokes,” she wrote via Instagram, sharing a photo of the actor playing with their daughter. “Oh well. Happpppppy Birthdayyyyyyyyy, Jason. I love you! 🎈.”

Sudeikis and Wilde stepped out to attend the premiere of her film, Life Itself, at the ArcLight Cinerama Dome in Hollywood.

The House alum revealed one thing she does with Sudeikis to keep the love alive in their relationship. “We go out and have a lot of fun,” she told Us at the time. “We were both really social people when we met, and we didn’t want to give that up when we became parents, so we’re really consistent about our time with them, but we also prioritize a couple of date nights a week.”

Sudeikis supported Wilde at the SXSW premiere of her directorial debut, Booksmart.

In honor of Father’s Day, Wilde shared adorable photos of Sudeikis with the couple’s children. “Wish I could say I was the fun one but we all know that’s not true. Happy Father’s Day my love! ❤️❤️❤️❤️❤️,” she wrote via Instagram.

Wilde and Sudeikis had a rare family outing with their two children at a Harlem Globetrotters game.

Sudeikis told Access Hollywood the reason he held off on kissing Wilde early on in their romance. “I just had a hunch that the second I kissed her, I wasn’t going to end up kissing ever kissing anyone ever again,” he explained. “So, it was like I had to be careful with it.”

After seven years of engagement, Us confirmed that the couple had called it quits.

After Wilde and Harry Styles sparked romance rumors, a source told Us that the Horrible Bosses star was "desperate" to win his ex back.

“Jason’s had no option but to step back and let Olivia do her thing, but he [has his fingers crossed] that this is just a phase and that Olivia will snap out of it or that Harry will get bored and move on before too long,” a source exclusively revealed to Us in January 2021.

“Congrats to Jason and the entire Ted Lasso family on your @CriticsChoice wins! @jasonsudeikis @hanwaddingham @brendanhunting @joekellyjk47 @VDOOZER!” Wilde tweeted in support of her ex in March 2021. “So happy for you guys.”

The actor, for his part, honored the Booksmart director during the virtual awards ceremony.

“Otis and Daisy’s mom, Olivia … had the initial idea to do this as a TV show,” Sudeikis said after winning Best Actor in a Comedy Series for Ted Lasso. “She was like, ‘You and Bill [Lawrence] and Joe [Kelly] love doing that so much you should do it as a TV show.’ I was like, ‘No.’ She was right.”

Following Sudeikis' growing romance with model Keeley Hazell, a source told Us that Wilde is "happy for him if he's happy with whomever he's dating."

The insider shared that the exes were "coparenting well."

"Olivia and Jason are better off as friends. They're doing their best at giving their kids a normal life. The kids bring them back together since they are and always will be their number one priority," the source added in July 2021.

Sudeikis spoke out about his split from Wilde for the first time during a candid interview with GQ. "I'll have a better understanding of why [it happened] in a year," he said at the time, asserting that the breakup occurred in November 2020. "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 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. ... 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."

While looking back on his first Golden Globes win, Sudeikis responded to cracks about his tie-dye sweatshirt, which went viral during the virtual awards show in February 2021.

"I wore that hoodie because I didn't wanna f—king wear the f—king top half of a Tom Ford suit," he told GQ. "I love Tom Ford suits. But it felt weird as s--t. ... I was neither high nor heartbroken."

The former couple made headlines when Wilde was served child custody papers while on stage at CinemaCon in Las Vegas. “Is this for me?” she asked after taking an envelope marked “personal and confidential” while promoting Don’t Worry Darling.

“Papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” a source told Us at the time, claiming Sudeikis was unaware of where his ex would be given the paperwork. “He would never condone her being served in such an inappropriate manner.”

Wilde responded to her former fiancé's custody filing with court docs of her own, slamming the comedian for publicly serving her at CinemaCon earlier in the year. "The fact that Jason would embarrass me professionally and put our personal conflict on public display in this manner is extremely contrary to our children's best interests," she alleged in docs obtained by the Daily Mail, claiming Sudeikis "clearly intended to threaten me and catch me off guard."

The actress noted that she and Sudeikis disagreed on where their children would spend the upcoming school year after initially planning to raise them in L.A. "He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible," she added.

For his part, Sudeikis offered an explanation for carrying out the exchange in public. "I did not want service to take place at the home of Olivia's current partner because Otis and Daisy might be present," he wrote, referring to Styles. "I did not want service to take place at the children's school because parents might be present. ... I understand that the process server had only done her job; however, I deeply regret what happened. Olivia's talk was an important event for Olivia, both professionally and personally, and I am very, very sorry that the incident marred her special moment."

Wilde and Sudeikis issued a rare joint statement after their former nanny spoke to the Daily Mail about their breakup. “As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make up such false and scurrilous accusations about us publicly,” they told Us at the time. “This is the unfortunate apex of a now, 18-month-long campaign of harassing us, as well as our loved ones, close friends and colleagues. 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.”

Among other things, the nanny claimed that Sudeikis “was out of control crying” when he discovered text messages from Styles on Wilde's Apple Watch. The former employee also alleged that Sudeikis was "infuriated" when he saw his then-fiancée preparing a salad for the "Golden" singer with her "special dressing."

The duo's former nanny Ericka Genaro sued them for discrimination, claiming that Sudeikis terminated her employment after she requested a three-day "leave of absence" to cope with anxiety and depression she alleged was caused by working for the former couple. In her complaint, Genaro also claimed that Wilde “abruptly left the home where she lived” with Sudeikis and the children in November 2020. “Wilde’s sudden absence from the home had an adverse consequence on its emotional state, including Sudeikis leaning on the presence of [Genaro] for support,” the docs continued. Genaro is seeking damages including “loss of earnings, deferred compensation and other employment benefits” and reimbursement for her legal fees.