Olivia Wilde’s Dating History: Tao Ruspoli To Harry Styles!

Olivia Wilde's Dating History: Tao Ruspoli To Harry Styles!

Olivia Jane Cockburn, better known by her stage name Olivia Wilde, was born in America on March 10, 1984. She has worked as an actor in both cinema and television. Wilde has acted in movies like Tron: Legacy, Cowboys & Aliens, In Time, and Drinking Buddies in addition to TV shows like The O.C., The Black Donnellys, and House.

The dating life of the actress, director, and filmmaker Olivia Wilde has been a major topic of discussion in recent years, particularly after she was linked to British pop sensation and actor Harry Styles in 2021.

Wilde’s great acting career has nearly always been accompanied by glamorous and high-profile relationships with in-demand celebrities and more, from her young marriage to an Italian prince to her very long engagement to a popular “Saturday Night Live” alum, to even having a child of her own.

If you want to know who Wilde has dated in the past, keep reading to find out about her famous (and even royal!) ex-boyfriends.

Olivia Wilde’s Dating Chart

Tao Ruspoli (2003-2011)

Wilde married Tao Ruspoli, an Italian director who is also a member of the Italian aristocracy when she was only 19 years old. Us Weekly said that the couple got married in an abandoned school bus. “It was a secret that we were getting married, so we wanted to do it somewhere we could hide with our best friends. It had everything to do with how close the promise we were making was, “Us later wrote about what Wilde told Playboy.

Olivia Wilde's Dating History: Tao Ruspoli To Harry Styles!

The couple was married for about eight years before they decided to split up. They asked for a divorce in February of 2011, and it was finalized in September of that year.

Also Read: Nick Cannon’s Dating History: Christina Milian To LaNisha Cole!

Ryan Gosling(February 2011)

Three weeks after announcing her breakup with Ruspoli in February 2011, Wilde and the Crazy, Stupid, Love actor were seen holding hands at an aquarium in Kentucky. This led to rumors that they were dating. Before that, they were seen having a casual brunch together at Nada restaurant in Cincinnati, Ohio, and getting close at the Golden Globes in January.

Justin Timberlake(April 2011)

After she was said to have met up with Gosling, Wilde was seen in April 2011 at a Hollywood club with her “In Time” co-star Justin Timberlake, who is now 39. But at the time, a source told People, “They’re just friends.”

Olivia Wilde's Dating History: Tao Ruspoli To Harry Styles!

Bradley Cooper (June 2011)

After the two-year relationship between the A Star Is Born actor and Renée Zellweger ended in 2011, some magazines reported in June that the two co-stars of The Words were “definitely hooking up.”

Jason Sudeikis (November 2011- November 2020)

People says that they started dating for the first time in November 2011. Wilde said that they fell “blissfully, hopelessly, wildly in love.” On The Late Show, Sudeikis told Stephen Colbert that they first met at an SNL afterparty. “We got along great that night. And the next thing you know, I wasn’t busy anymore, she wasn’t dating anyone anymore, and we were off to the races.”

Olivia Wilde's Dating History: Tao Ruspoli To Harry Styles!

They got engaged in 2013, but they didn’t get married. Instead, they stayed engaged for the next seven years. During that time, they had two children: a son named Otis in 2014 and a daughter named Daisy in 2016. In November 2020, the couple told everyone that they had broken up earlier in the year.

Also Read: Meghan Markle’s Dating History: An Inside Look!

Harry Styles (January 2021-Present)

The director was seen at a friend’s wedding with the “Watermelon Sugar” singer in January 2021, which led to them being linked. A source told Us that the two “had chemistry almost right away” while working on the set of their movie, Don’t Worry, Darling, which she also directed.

Olivia Wilde's Dating History: Tao Ruspoli To Harry Styles!

Most recently, Wilde discussed her relationship with Styles and shot down allegations that she had abandoned Sudeikis for the musician in a cover article for Vanity Fair.

She added, “It’s a complete horses—- that people think I left Jason for Harry. I met Harry after our relationship had already ended.

Wilde also explained why she makes an effort to maintain the secrecy of her relationship with Styles. She said, “I don’t think if you crack open the window, you can then be outraged when mosquitoes come in. It sounds like “You opened the window,”

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