Olivia Wilde’s Dating History Through the Years: Jason Sudeikis, Harry Styles and More

Love on her terms! As a highly sought-after A-list actress, Olivia Wilde can have her pick of Hollywood’s most notable men. Wilde, born Olivia Jane Cockburn, married Italian-American filmmaker Tao Ruspoli when she was just 19 years old. While explaining their decision to elope, the House alum admitted that it was initially “hard to imagine settling down” at such a young age. “But there was this wave of romantic excitement and an overwhelming sense that we were supposed to be family,” she told Women’s Health in 2008. “We were very open to the idea that if it didn’t work, we would let it go its course. No pressure.” The duo parted ways in 2011 after eight years of marriage. The Washington, D.C. native has since acknowledged that she feels she got married too young. “I really had a sense that I had stunted my growth. I think that’s one of the things that made me feel so uncomfortable in my marriage,” she said on Lifetime’s The Conversation in 2012. “It was really no fault of my husband. It was me realizing that I had sort of arrested development. I knew the only way I was going to grow the f--k up was to learn to take care of myself.” [jwplayer byUhKwaj-l3ahXupL] Wilde later appeared to find her happily ever after with Jason Sudeikis, who she began dating in late 2011 after his marriage to filmmaker Kay Cannon ended in 2010. Following the pair’s engagement in 2013 after two years of dating, they welcomed son Otis in 2014 and daughter Daisy in 2016. The Butter actress referred to the Ted Lasso actor as “the great love of my life” in a Marie Clarie interview from 2013, adding, “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.” Us Weekly confirmed in November 2020 that the longtime couple had called it quits after nine years together. “They’ve been separated for months now and there really is no drama. They’re handling this like adults. It’s all about coparenting their kids, Daisy and Otis. That’s the priority for them,” a source exclusively told Us. Following the news of their split, the Booksmart director turned heads in January 2021 after being linked to her Don’t Worry Darling colleague Harry Styles. The duo were photographed attending Styles’ manager Jeffrey Azoff’s intimate wedding ceremony. The “Lights Up” crooner even referred to Wilde as his “girlfriend” while officiating the event, a source told Us. “Harry and Olivia had chemistry almost instantaneously on set,” a second insider revealed. “It was only a matter of time before they got together.”

Us confirmed in November 2022 that the twosome had split after nearly two years together.

Scroll down to explore Wilde’s dating history through the years. [podcast_block]

The Tron: Legacy actress was married to the son of Prince Alessandro Ruspoli from 2003 to 2011. She filed for divorce in March 2011 citing “irreconcilable differences” and their case was finalized that September.

Three weeks after announcing her split from Ruspoli in February 2011, Wilde sparked dating rumors with the Crazy, Stupid, Love actor when they were spotted holding hands at an aquarium in Kentucky in March 2011. Before that, they were seen enjoying a casual brunch together at Nada restaurant in Cincinnati, Ohio, and getting cozy at the Golden Globes that January.

Wilde was linked to the “Can’t Stop the Feeling” crooner in April 2011 while he was on a break from now-wife Jessica Biel. After they were spotted dancing and flirting in L.A., a source told Us that the In Time costars “were obviously a couple or on a date.” She later slammed the dating speculation, tweeting, “Cool it, honeybadgers. We are just friends and have been for years.”

After the A Star Is Born actor ended his two-year relationship with Renée Zellweger in 2011, Us revealed that June that The Words costars were “definitely hooking up.”

Wilde met Sudeikis in May 2011 at a Saturday Night Live wrap party following the season 36 finale. They began dating that November and got engaged in 2013. Us confirmed in November 2020 that the Drinking Buddies costars — who share Otis (born in 2014) and Daisy (born in 2016) — split after nine years together.

The filmmaker was linked to the “Watermelon Sugar” crooner in January 2021 when they were photographed attending his pal’s wedding together. A source told Us that the pair “had chemistry almost instantaneously” while working on the set of their film, Don’t Worry Darling, in which she also directs.

In November 2022, Us confirmed that the pair split after less than two years of dating.