After stepping out with Harry Styles, actress Olivia Wilde’s colourful relationship history has been revealed.
After stepping out with Harry Styles, actress Olivia Wilde’s colourful relationship history has been revealed.

Inside movie star’s wild dating history

When Hollywood actress and director Olivia Wilde nabbed One Direction hunk Harry Styles for her latest movie, she "did a little victory dance".

Back then, the 36-year-old was only interested in what the singer's "appreciation for fashion and style" would bring to the role in upcoming horror thriller, Don't Worry Darling.

Fast forward a few months and their creative partnership has developed into a romantic one - the latest in Olivia's colourful love life, which has seen her secretly marry a prince, go on a 'sex bender' and describe how she and a partner romped "like Kenyan marathon runners".

News emerged yesterday Olivia and Harry, 26, were seen holding hands at the One Direction star's agent's wedding in Montecito, California, last weekend, having driven there in Harry's vintage convertible.


Olivia Wilde. Picture: Frederick M. Brown/Getty Images
Olivia Wilde. Picture: Frederick M. Brown/Getty Images

It was a COVID-safe event with just 16 guests, in which Harry conducted the ceremony and took Olivia as his plus one.

A source said: "They're both very artistic, passionate people and it was one of those things where straight away everyone could see they had a spark.

"It's no surprise something has happened, but now they're quite open about it and out and about as a couple."

Harry Styles fans, never keen to admit their handsome hero has a new love interest, yesterday poured cold water on the news.

Some posted pictures of him holding hands with James Corden and Niall Horan, sarcastically commenting that it must mean they are a couple.

Others suggested the Sign Of The Times singer was purely supporting a friend after the end of her long-term relationship.

Olivia, whose directorial debut Booksmart earned critical acclaim in 2019, revealed in November that she and Horrible Bosses actor Jason Sudeikis had split early last year.

It was said they simply couldn't make their "bicoastal" marriage work, with Olivia's work putting her firmly in Los Angeles and Jason preferring New York.


One source said they "butted heads on many occasions and decided it was best to go their separate ways".

Olivia and the Saturday Night Live funnyman now co-parent their children, Otis, 6, and Daisy, 4.

But while Olivia is not on the same level of extreme fame as Harry, her past is almost as colourful as the singer's, whose 18 ex-girlfriends include pop star Taylor Swift and supermodel Kendall Jenner.

As a teenager, Olivia secretly married Italian prince Tao Ruspoli who lived on a school bus, and went on a sex bender when they eventually split, according toThe Sun.

She was just 19 when she and Tao, a filmmaker and musician, met via a family friend.

His aristocratic family owns a famed palazzo and castle in Italy, but Tao led a much more humble life.

Olivia once told Women's Health magazine: "Everyone expects him to pick me up in a limo or a yacht. Then Tao rolls up in this old Thunderbird, wearing flip flops, his hair all crazy.

"People are like, 'He's a prince?'"

Explaining it was only a "papal title", Olivia said it did still make her "feel like a princess".

RELATED: Olivia's cryptic post after Jason split

Olivia Wilde and her ex-husband Tao Ruspoli. Picture: Kevork Djansezian/Getty Images
Olivia Wilde and her ex-husband Tao Ruspoli. Picture: Kevork Djansezian/Getty Images

They married on Tao's school bus with just a couple of witnesses.

She said: "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. We were very open to the idea that if it didn't work, we would let it go its course. No pressure."

It didn't work out, but the pair were together for eight years, splitting in February 2011.

Afterwards, Tao made a documentary called Monogamish, which seemed to stem from his heartbreak.

He says in the film: "My wife has just left me after nearly 10 years together and my whole world crumbled."

There is no animosity though. He said in 2016, he had "nothing but good feelings towards her and nothing but gratitude for the time we spent together".

He added: "It was amazing to see her propelled into stardom and a fascinating front-row seat at something not many people get to witness."

In 2012, Olivia made a deeply personal revelation about the end of her marriage while she was talking to friends at a pub in New York, where she was taking part in the theatre production Glamour Presents These Girls.

She said: "I felt like my vagina died. Turned off. Lights out. And you can lie to your relatives at Christmas dinner and tell them everything on the home front is just peachy. But you cannot lie to your vagina."

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Olivia at the Emmys in 2009. Picture: Chris Pizzello/AP
Olivia at the Emmys in 2009. Picture: Chris Pizzello/AP

When her comments made it into the press, she hit out, saying the monologues were "not meant for publication, and in context, were a celebration of LOVE, girls and honesty".

She added: "Sneaky recorders are everywhere these days, but performance art doesn't always translate accurately to tabloid interpretation."

After spending her 20s as a wife, Olivia briefly took advantage of her new-found freedom by going on what one magazine dubbed a "sex bender".

It wasn't fulfilling and at one point she felt so lonely she told the audience at These Girls that she considered "a soft kind of lesbian relationship, just gentle kissing and scissoring".

Then she crossed paths with Jason at a Saturday Night Live after-party, where she admired his dance moves and he came out with what she called "the greatest line".

He said: "Whatever you're looking for, you don't need it."


Fate brought them together several times over the next six months until eventually one of Olivia's best male friends gave Jason her number.

Even then Jason didn't text her for a month, and they only kissed on their fourth date.

Olivia said: "He played it so cool. He finally kissed me and I was completely head over heels."

There were fireworks from the off, and Olivia once proclaimed: "We have sex like Kenyan marathon runners."

The pair at a basketball game when they began dating in 2011. Picture: Orlin Wagner/AP
The pair at a basketball game when they began dating in 2011. Picture: Orlin Wagner/AP

They split after nine years together last year, ending their long-running engagement.

Olivia, who was born Olivia Cockburn in New York and grew up in Georgetown, Washington D.C, comes from a family of journalists.

One of her great great grandfathers, Henry Arthur Blake, was governor of Hong Kong and the family is descended from Scottish lawyer and literary figure Henry Cockburn, Lord Cockburn.

Olivia later changed her surname to Wilde, inspired by playwright Oscar Wilde.

She once said in her perfect "Olivia Land" relationships would only be allowed to last seven years.

She said: "That way it never goes stale. Can you imagine, we only had seven years? We'd be so nice to each other, so kind and appreciative and enthusiastic, like we were eating a really expensive bowl of pasta."

Harry wasn't originally intended to play the lead part of Jack in Don't Worry Darling. It had gone to scandal-hit Shia LaBeouf, but he dropped out due to a "scheduling conflict".

However, after British singer FKA Twigs accused him of physical and emotional abuse in their relationship, sources close to the film said it was Shia's "off-putting" behaviour combined with Olivia's "zero a**hole policy" that ended his contract.


The film, a psychological thriller centred on an unhappy housewife (played by British actress Florence Pugh) in the 1950s, in which Olivia acts as well as directs, also stars Crazy Rich Asians actress Gemma Chan.

Harry, who splits his time between London and Los Angeles, is said to have been living at UK TV host James Corden's home in Palm Springs, which has provided privacy for the new couple.

This story originally appeared on The Sun and has been reproduced here with permission



Originally published as Inside movie star's wild dating history