Olivia Wilde (2011-2020)
Sudeikis's most highly-publicized relationship was with actor and director Olivia Wilde. According to People, the pair met at a "Saturday Night Live" afterparty in May 2011. Sudeikis opened up about their encounter while appearing on "The Late Show with Stephen Colbert" in April 2017. "We hit it off that night," he said. Since Wilde was dating someone else at the time, Sudeikis said he "didn't make any moves," but once she was single, he said "it was off to the races" for the couple.
In an October 2013 interview with Allure (via People), Wilde said she thought Sudeikis was "so charming" when they met, but noted that he didn't ask for her phone number right away. After the stars kept running into each other for months, one of Wilde's friends helped the pair finally get together. "[One night], my best guy friend walked up to him and said, 'This is Olivia's number. Use it,'" she said. "That was the beginning."
Sudeikis and Wilde officially began dating in November 2011. Then, in January 2013, People reported the couple had gotten engaged shortly after the holidays. "They are so excited," a source told the publication. "And very, very happy."
A year later, the stars welcomed their first child — a son named Otis Alexander — in April 2014. "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I'm the building)," Wilde tweeted at the time.
In April 2016, the former couple welcomed a daughter named Daisy Josephine. "There goes the neighbourhood. Daisy Josephine Sudeikis. Born, like a boss, on #internationaldayofthegirl," Wilde wrote on Instagram, alongside a photo of the newborn.
After welcoming their second child together, Sudeikis and Wilde remained engaged for four more years before People reported in November 2020 the pair had called it quits. "The split happened at the beginning of the year," a source said at the time. "It's been amicable and they've transitioned into a great co-parenting routine. The children are the priority and the heart of the family's relationship."
Just days after the news broke, the stars were photographed hugging in photos obtained by People. While they appeared to be on good terms, things seemingly changed after Wilde moved on with Harry Styles. In January 2021, she and the singer were spotted holding hands at a wedding, sparking rumours they were an item. "They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks," a source told People.
After photos of the pair surfaced, a source also told the publication that Sudeikis was "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 source said. "But what happens next remains to be seen."
In April 2022, things between the exes grew even more complicated when the "Booksmart" director was served legal documents while she was on stage at CinemaCon. According to Vanity Fair, those documents turned out to be custody papers from Sudeikis involving the pair's two children. Following the whole ordeal, a source told People that Sudeikis "had no prior knowledge" of when or where Wilde would receive the papers. "He would never condone her being served in such an inappropriate manner," the source said.
That August, Wilde filed to dismiss the custody petition. "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, according to the Daily Mail. Amid the drama, People reported the stars weren't speaking but hoped to "figure out the best living situation for everyone."
In January 2023, the exes were spotted hugging in photos obtained by Page Six, just two months after news came out that the "Tron: Legacy" actor had broken up with Styles. So, while Sudeikis and Wilde are no longer together, it seems they have made amends and are focusing on coparenting their children.