Olivia Wilde's Dating History Includes A Prince She Married On A School Bus

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There's no doubt about it: Olivia Wilde is one of the most accomplished women in Hollywood, and there's only a handful of guys who really know what it's like to date her. Olivia Wilde's dating history includes some impressive A-listers, but there is only one man who she referred to as "the great love of my life" in a 2013 story with Marie Claire — and that was Jason Sudeikis. The couple was together for nearly a decade, but unfortunately, things didn't work out between the two, and they ended up announcing their breakup November 2020.

Even though I was a little heartbroken to see them split up, Wilde appears to have found love again with One Direction alum Harry Styles. In January 2021, the two were caught holding hands while attending Styles' manager Jeffrey Azoff and Apple Music's Glenne Christiaansen's wedding. Soon after, a source for People reportedly claimed they have been dating "for a few weeks" already.

Looks like Wilde hasn't given up on finding her Prince Charming! For all I know, Styles could be the perfect guy for her. But if you want to know more about the men she's dated in Hollywood, then here's a quick recap.

Tao Ruspoli, 2002-2011
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In a 2008 interview with Women's Health, Wilde revealed she met filmmaker Tao Ruspoli (who also happens to be the son of the Prince of Cerveteri) in late 2002 through a family friend. But even though she wasn't eager to meet him since he "lived on a school bus," Wilde still went on a date with the Italian prince and ended up eloping with him in June 2003 on that same school bus she criticized before.

Once they were married, the pair worked together on multiple projects, like the 2006 movie Camjackers and the 2008 film Fix. However, their love eventually came to an end in March 2011, which is when they decided to get a divorce and go their separate ways.

Ryan Gosling, 2011
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In January 2011, Wilde reportedly met Ryan Gosling at Relativity Media's Golden Globes party, per Marie Claire UK. However, dating rumors didn't start to circulate until March 2011, when the pair was reportedly spotted holding hands at a Cincinnati aquarium, which was close to where Gosling filmed the political drama The Ides of March with George Clooney. However, Wilde and Gosling's relationship appears to be short-lived, as she was linked to another notable star just one month later.

Justin Timberlake, 2011
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When Justin Timberlake and his now-wife, Jessica Biel, were on a break, the pop star reportedly dated Wilde for a short amount of time. In April 2011, a source for Us Weekly reportedly claimed the duo was spotted getting friendly at the L.A club hotspot Roxbury, where they were reportedly "dancing all night."

"They were obviously a couple or on a date," the insider reportedly claimed. "They were dancing, whispering, he had his hand on her back and shoulders and they were together all night." Not only that, but another source reportedly claimed Wilde and Timberlake paid close attention to each other all night. "His arm was around her, they were talking closely, just the two of them," the insider reportedly claimed. "Justin and Olivia were there with a group, but weren't talking to anyone else." But just like with Gosling, romance rumors soon fizzled out.

Bradley Cooper, 2011
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Bradley Cooper is another man who reportedly romanced Wilde. According to Us Weekly, the duo met in 2010 when Wilde auditioned for Cooper's film Limitless, but they didn't reconnect until May 2011, when Wilde attended Cooper's afterparty for The Hangover Part II in New York City. During that time, Cooper was fresh out of a relationship with his girlfriend of two years, Renée Zellweger.

"They're definitely hooking up," a source reportedly claimed to Us Weekly at the time about Wilde and Cooper. Life & Style also shared pictures in which the two seemed to be talking in the VIP booth during the event. "He took care of her all night," a source reportedly claimed to the magazine. "He was always taking her hand or putting his hand on her lower back, it was really sweet." Although Life & Style claims that Wilde and Cooper left the event together, they apparently didn't end up together, because Wilde started dating someone else just months later.

Jason Sudeikis, 2011-2020
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In May 2011, Wilde met her next boyfriend, Jason Sudeikis, at a Saturday Night Live wrap party. They apparently hit it off, because they started dating that November and got engaged in January 2013 shortly after the holidays. During a September 2013 interview with Allure, Wilde recounted their first interaction. "I met Jason, and I thought he was so charming," she said. "He's a great dancer, and I'm a sucker for great dancers."

In April 2014, Wilde and Sudeikis welcomed their son, Otis, and two-and-a-half years later, they had a daughter, Daisy. Sadly, the relationship didn't last. Even though the news of Wilde's split from Sudeikis only went public in November 2020, she and her ex-fiancé reportedly called it quits "almost a year ago," according to the source for Entertainment Tonight, but they seem to be on good terms. "Olivia and Jason talk all the time and are still close because of the kids," the insider reportedly claimed.

Harry Styles, 2020-2021
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Wilde has most recently been linked to Harry Styles. Fans first learned the duo could possibly be dating when they were seen holding hands at a friend's wedding in January 2021. Styles and Wilde reportedly became close over the fall while filming Don't Worry Darling, an upcoming movie directed by Wilde and starring Styles. "Harry and Olivia had chemistry almost instantaneously on set," a source for Us Weekly reportedly claimed, adding, "It was only a matter of time before they got together."

Although her latest romance seems to be new (and has yet to be confirmed), I have a good feeling about Wilde and Styles!