Olivia Wilde's Dating History: From Italian Royalty To Harry Styles

Entertainment
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Alexandra Lozovschi

Olivia Wilde had fans swooning over her romance with Harry Styles when the celebrity couple made their relationship public at the beginning of the year. But the British pop star is not the only famous name that she has dated.

The 37-year-old Tron: Legacy star, whose career as an actress, model, and movie director has earned her a net worth of $20 million, has been linked to quite a few Hollywood hunks before finding happiness with the 27-year-old singer.

She was previously engaged to SNL comic Jason Sudeikis, with whom she shares two children, and even married an Italian prince at one point.

While her Instagram page gives little clues about her romantic and personal life and is mostly devoted to her work and her kids, we've compiled a list of Wilde's former boyfriends, ex-husband included. Details below.

2003-2011: Tao Ruspoli

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Wilde was only 19 when she met and fell in love with Prince Tao Ruspoli, son of Prince Alessandro Ruspoli aka the 9th Prince of Cerveteri. Nine years her senior, he was a filmmaker at the time and lived on a bus, she told Women's Health magazine in 2008.

It was on that same bus that Wilde and Ruspoli, now 46, eloped just six months after they started dating in 2003.

"There was this wave of romantic excitement and an overwhelming sense that we were supposed to be family,” Wilde recounted. “We were very open to the idea that if it didn’t work, we would let it go its course. No pressure.”

The whirlwind nuptials were followed by a nearly nine-year marriage, with the couple splitting in February 2011 and filing for divorce a month later. The actress opened up about their relationship in a 2013 interview with Marie Claire, saying they had "drifted apart."

She has also revealed that getting married so young had "stunted" her "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.”

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2011: Ryan Gosling (Rumored)

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Just three weeks after Wilde and her ex-husband called it quits, the Cowboys & Aliens actress was linked to The Notebook star Ryan Gosling, now 40. The pair reportedly looked very chummy at the Golden Globes in January 2011 and were later spotted having dinner together at Ohio Nada restaurant in February while Gosling filmed The Ides of March in Cincinnati.

However, it was their aquarium date in March that sent tongues wagging about a possible romance. With neither one of them addressing the rumors, their alleged relationship was most likely purely gossip.

2011: Justin Timberlake (Rumored)

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One month after her rumored fling with Gosling, Wilde was linked to yet another Hollywood heartthrob. When she and her In Time co-star Justin Timberlake, now 40, were spotted at a Los Angeles club on what appeared to be a date in April 2011, the media began speculating they were hooking up.

At the time, the Palmer actor, who also worked together with Wilde on Alpha Dog, was on a break from his now-wife Jessica Biel, with Us Weekly calling their night out a "double rebound."

Nevertheless, it seems there was nothing going on between the two, as Wilde clarified on Twitter: “Cool it, honeybadgers. We are just friends and have been for years.”

2011: Bradley Cooper (Rumored)

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In May 2011, romance rumors started flying off yet again when Wilde was seen in the company of a third dashing gent post-divorce. According to US Weekly, The Change-Up star attended a VIP booth party for The Hangover II with Bradley Cooper, now 46, with a source telling the news outlet they were "definitely hooking up."

"Olivia acted jealous when other girls came up to him," said the source. "She thought going with Bradley would make JT jealous."

2011-2020: Jason Sudeikis

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Wilde met the man whom she would later describe as “the great love of my life,” Jason Sudeikis, at the SNL 2011 finale party in May. Although they immediately hit it off, it took him six months to ask her out, the House alum told Marie Claire,

"He was so cool, so funny — 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," she shared.

Meanwhile, Sudeikis, now 46, told Stephen Colbert on The Late Show in 2017: "I actually came off looking a little cooler than I really am because I had heard through the grapevine, through mutual friends who weren’t exactly her best girlfriends, who would report back, ‘Oh you know, I think she’s dating someone.'"

The Drinking Buddies costars started seeing each other that November. One year later, the We're The Millers actor popped the question and the pair got engaged in 2013. The couple welcomed their first child together, son Otis, in 2014. Two years later, their daughter Daisy was born.

Although they seemed like a match made in heaven, Wilde and Sudeikis called off their engagement after seven years in November 2020. They were together for nine years in total.

“They’ve been separated for months now and there really is no drama," a source told Us Weekly at the time. "They’re handling this like adults. It’s all about co-parenting their kids, Daisy and Otis. That’s the priority for them.”

According to Page Six, the exes "seem to have the best breakup in Hollywood, and have been photographed embracing numerous times since the split."

2021: Harry Styles

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The Booksmart director and the “Watermelon Sugar” singer made a splash in January when they were photographed holding hands at Styles’ manager Jeffrey Azoff’s intimate wedding ceremony in California. The singer even referred to Wilde as his "girlfriend" while officiating the event, a source told US Weekly.

“Harry and Olivia had chemistry almost instantaneously on set,” a second insider revealed in reference to their film, Don’t Worry Darling, in which she also directs. “It was only a matter of time before they got together.

The couple has been dating ever since, with Harper's Bazaar detailing the timeline of their relationship throughout the year.

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