Olivia Wilde and Jason Sudeikis had a low-key Hollywood romance that all began during a late-night Saturday Night Live afterparty.
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.”
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.’”
The longtime couple’s romance came to an end in 2020, when Us Weekly confirmed that they had called off their engagement.
Scroll down to see a complete timeline of Wilde and Sudeikis’ romance throughout the years.
Wilde first met Sudeikis while attending a Saturday Night Live wrap party following the sketch comedy show’s season 36 finale.
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The acting duo struck up a romantic relationship six months after meeting.
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It was announced that Sudeikis proposed to Wilde after two year years of dating.
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Sudeikis appeared in Wilde’s indie movie Drinking Buddies.
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Wilde was pregnant with the engaged couple’s first child.
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The Butter actress gave birth to the duo’s first child, Otis.
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Wilde posted a candid photo to Instagram of the couple kissing, writing, “Best part of a great night. ❤️.”
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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.”
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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.
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The couple welcomed their second child together, Daisy.
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Wilde posted a sweet photo of the longtime couple staring into one another’s eyes. “#❤,” she wrote that Valentine’s Day.
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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! 🎈.”
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Sudeikis and Wilde stepped out to attend the premiere of her film, Life Itself, at the ArcLight Cinerama Dome in Hollywood.
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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.”
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Sudeikis supported Wilde at the SXSW premiere of her directorial debut, Booksmart.
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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.
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Wilde and Sudeikis had a rare family outing with their two children at a Harlem Globetrotters game.
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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.”
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After seven years of engagement, Us confirmed that the couple had called off their engagement.
Jason Merritt/Radarpics/Shutterstockfrom Celebrity News – Us Weekly https://bit.ly/2W5lwbh
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