Has Olivia Wilde had any relationships before Harry Styles? The Complete Dating History of the Actress!

Olivia Wilde’s dating life has been in the spotlight for quite some time now, especially after she was linked to British pop sensation and actor Harry Styles in 2021.

Wilde’s successful acting career has almost always been accompanied by glamorous and high-profile relationships with in-demand entertainers and more.

From her early marriage to an Italian prince to her long engagement to a famous “Saturday Night Live” alum and even the birth of her child, Wilde has had no shortage of high-profile partners.

There’s no denying that Wilde’s love life is flourishing at the same rate as her outstanding job right now, but who has she dated in the past, and more importantly, why did they break up?

Also Read: Reports Reveal Harry Styles and Olivia Wilde Have Split

Read on to find out all the gory details about Olivia Wilde’s previous and present relationships, from the casual to the deeply passionate.

In 2003, Olivia Wilde wed director Tao Ruspoli.

In 2003, Olivia Wilde met Tao Ruspoli, an Italian director and aristocrat, and they eloped after six months of meeting. Wilde was only 19 when he wed in Virginia.

In an interview with Women’s Health published in 2008, Wilde reflected on the whirlwind romance, saying, “My dad did have a minor heart attack, and it was hard to imagine settling down at the time, but there was this wave of romantic excitement and an overwhelming sense that we were supposed to be family.”

If it didn’t work, we would let nature take its course. There’s no need to worry. Later, in 2008, Wilde and Ruspoli made a movie together titled “Fix.”

Wilde often commented on the fact that her husband was not what others might have expected from a prince, despite his royal title.

“Everyone expects him to pick me up in a limo or a yacht,” she said, according to Women’s Health.

Then Tao arrives in his beat-up old Thunderbird, sandals on his feet and his hair in a wild style. “He’s a prince?” many have asked.

The divorce between Wilde and Ruspoli was finalized in 2011.

Olivia Wilde filed for divorce from Tao Ruspoli on the grounds of irreconcilable differences in March 2011, after a month during which a representative for the couple publicly announced their separation.

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I grew up with Tao; we just drifted apart, Wilde told Marie Claire in 2013. It was as if I were trying to prove myself.

If you fall off a horse, you simply hop back on and continue riding. To put it bluntly, I do not give up easily.

I clung for as long as I could, until it hurt more to be there. “I am very thankful for the suffering and the heartache,” she continued.

This experience gave me the confidence to leave and led me to the person I would spend the rest of my life with.

Ruspoli did not discuss the divorce at the time, but in 2014 (according to IMDb), he released a documentary called “Monogamish,” in which he discussed his feelings at the time.

“I’m in a situation of an absolute catastrophe,” he read from a letter. After nearly a decade of marriage, my wife has abruptly left me. My entire world has collapsed.

Different people were interviewed about sexuality, relationships, and marriage in this documentary to determine whether or not the concept of monogamy is inherently human.

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In late 2011, she started dating actor Jason Sudeikis.

Olivia Wilde’s “great love” turned out to be actor and comedian Jason Sudeikis.

In November 2011, rumors of a romance between the two began circulating. Six months after their initial meeting at a “Saturday Night Live” season finale after-party, the two started dating.

“I was just very, very busy with other stuff,” Sudeikis told Stephen Colbert . And then suddenly I wasn’t so busy, and she wasn’t seeing anyone else, and we were off to the races.

We gave each other a second chance at an introduction. This autumn had additional surprises from the cosmos. When the two were finally together, they took things carefully.

“When he obtained my number, he didn’t text me for a month,” Wilde said to Howard Stern. On our fourth date, he finally kissed me. When he kissed me, it was the final straw.

The following year, USA Today reported that Wilde and Sudeikis had moved in together in Manhattan.

In 2013, Wilde and Sudeikis became engaged.

Olivia Wilde and Jason Sudeikis got engaged over the 2012 holidays and made the announcement in January 2013. They had been dating for only a year at the time .

Later that year, in an interview with InStyle, Sudeikis raved about how much he admired Wilde’s charisma and excellent looks.

He gushed about her at the time, saying, “She is a blend of everything that I love about women.

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She is brilliant, strong, kind, attractive, and as hilarious as anybody I’ve known. It seems like she has it all.

The pair had been engaged for some time, but no wedding date was ever announced. Wilde expressed her hope for a prolonged engagement to Vanity Fair, remarking,

“It’s funny, people tend to skip over the engagement thing. They think it’s like, ‘Oh, engaged.’ And then you get there.

I don’t think you should spend your entire engagement planning a wedding. Because it’s fun. It’s this great time. It’s like dating-plus.”

They have two children, a boy and a girl.

Late in 2012, Olivia Wilde discussed her future plans to start a family.

In an interview with USA Today, she reflected on her mother as a role model for balancing work and motherhood. That’s not to say it can’t be accomplished.

Nobody is claiming that it’s simple. However, the thought of being a formidable working professional mother motivates me much.

My dog and I have a really close relationship. What will I do to suffocate my child?

Wilde and Jason Sudeikis had their first child, a son named Otis Alexander, in April 2014.

Otis Alexander Sudeikis has LEFT the building!” Wilde joked on Twitter after the birth. As in, “(I’m the structure)”

Wilde announced her second pregnancy to Instagram followers in 2016, two years after the pair had their first child.

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She posted a photo of herself and Otis clutching their growing bellies and captioned it, “Matching baby bumps.”

Wilde and Sudeikis had a second child, a daughter they called Daisy Josephine, later that year, and she made the announcement on Instagram.

After 9 years of marriage, Wilde and Sudeikis broke up.

In November of 2020, news broke that Olivia Wilde and Jason Sudekis had broken up, and the entire world was distraught.

People stated that Wilde shared a nice snapshot of her two children on her Instagram Story with the comment “My everythings” hours after the news of the split went public.

While discussing the breakup with GQ in August 2021, Sudeikis said, “I’ll have a better understanding of why in a year,” he said, “and an even better one in two, and an even greater one in five, and it’ll go from being, you know, a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle.”

While promoting her new picture “Don’t Worry Darling” at CinemaCon in April 2022, Wilde was served with custody papers by Sudeikis.

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In 2021, she started dating Harry Styles.

When Olivia Wilde and Harry Styles were spotted coming at manager Jeff Azoff’s wedding in Montecito, California, hand-in-hand in January 2021, the news spread like wildfire.

Styles and Wilde first crossed paths in September of 2020 on the set of the film “Don’t Worry Darling,” which Wilde directed and in which Styles starred.

In the latter part of 2021, Source reported that the new pair had been sighted on a trip to Italy.

In addition to attending several of Styles’ shows, Wilde was spotted dancing and singing along at others.

Howard Stern interviewed Styles in May 2022, and the radio host asked the young star if he “fell in love” while filming “Don’t Worry Darling” .

“Oh my goodness, what do I say to that?” As expected, the response came from Styles. Being directed by Olivia was a fantastic experience for me.

It’s evident to me that there’s something about acting that can be quite unsettling at times. I believe a great deal of trust is required. Trusting your director is a rare and precious commodity.

Although they both have busy schedules due to their careers and Styles’ constant touring, the couple was spotted on vacation together in Italy again that same month, thus confirming that their love is still going strong.