Olivia Wilde's relationship history as she 'dates Harry Styles'

Just days into 2021, we were gifted with a new celebrity couple to obsess over, courtesy of Olivia Wilde and Harry Styles.

The pair, who are working on the upcoming film Don’t Worry Darling together, appeared to confirm they are dating after they were pictured holding hands at Harry’s agent’s wedding.

While there is always interest in Harry’s love life, being a former teen heartthrob and chart-topping superstar and all that, there is also plenty of chatter about Olivia’s romance history.

The 36-year-old actress has been married once before, after she tied the knot with an Italian prince as a teenager.

Olivia was 19 years old when she was introduced to Tao Ruspoli by a friend of her parents in 2003.

She told Women’s Health in 2008: ‘He wanted to introduce me to this Italian guy who made films and lived on a school bus. I said, “Whoa! I don’t want to meet a dude who lives on a bus!”’

However, she and Tao – an Italian prince whose family own a palazzo in Rome and a castle in Vignanello, as well as a filmmaker – hit it off, and six months later, they eloped on a bus.

Olivia admitted her father had a ‘minor heart attack’ over their elopement, with the couple having a ‘proper’ wedding later in Virginia.

However, Olivia filed for divorce in March 2011, citing irreconcilable differences.

Speaking to Marie Claire, she explained: ‘Even though it didn’t work, there’s nothing I regret about any of it. We’re friends; his family is my family. You always have a choice to feel angry and not be friends. But I can’t handle the idea of walking into a room and seeing someone I have bad blood with. I can’t keep any negative relationship with anyone. 

‘Our deal from the beginning was, “We’re crazy to do this, but we’re doing it because we’re in love and it makes us happy. The only reason to divorce is if one of us isn’t happy. Life is too short.” After really trying to make the relationship evolve in the way our lives had, I realised it wasn’t a natural evolution. 

‘When the relationship becomes about working to make it work, it’s lost that beauty and that optimistic bohemian sense that brought us together. I don’t think love should be work. My parents have been married for 35 years. They said, “You have to work at it. That’s what it takes.” But we tried, and it wasn’t making us happy.’

Months later, Olivia met Horrible Bosses actor Jason Sudeikis at Saturday Night Live, but their romance wasn’t instant.

Jason, 45, told Stephen Colbert in 2017: ‘I met her at a finale party for SNL. We hit it off that night.

‘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”. So I didn’t make any moves. I was just very, very busy with other things. And next thing you know, I stopped being busy, she stopped dating someone, and then it was off to the races. 

‘We sort of reintroduced ourselves. The universe had more in store for us in the fall.’ 

Olivia told Allure a year after their engagement that she thought the actor was ‘charming’, but that he didn’t ask for her number when they met. 

The OC star said: ‘Over the next six months we kept running into each other. [One night], my best guy friend walked up to him and said, “This is Olivia’s number. Use it.” That was the beginning.’

The pair started dating in November 2011, with Jason popping the question in January 2013, and they welcomed two children together – Otis Alexander, six, and Daisy Josephine, four.

Over their relationship, Jason had a role alongside his fiancée in the 2013 film Drinking Buddies, while Olivia cast her partner as the principal in her directorial debut Booksmart in 2019.

Speaking about Jason’s performance in the smash comedy, the actress said: ‘He’s one of the best improvisers in the world so I knew I could cast him. He’s like spinning a top and just letting it roll. It’s really amazing to see him do his thing.’

However, in November, it was reported that Olivia and Jason had ended their engagement after seven years at the start of 2020. 

A source told People: ‘It’s been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship.’

Now, Olivia has found herself in a new high-profile relationship, with Harry Styles, who is 10 years her junior.

Olivia cast Harry Styles in her upcoming psychological horror Don’t Worry Darling, alongside Florence Pugh, Chris Pine, Gemma Chan and KiKi Layne, with Olivia both directing and starring in the movie.

It seems sparks flew on set, as the pair seemed in couple mode as they held hands at Jeff Azoff’s wedding wearing matching face masks from The Vampire’s Wife.

According to Page Six, the stars had been spending time together at James Corden’s house as well as on set, with a source claiming: ‘This relationship between Harry and Olivia is very new. Olivia has been directing Harry in the movie in Palm Springs, and there were literally 10 people on the set, because they were strictly adhering to COVID rules. 

‘Harry had been staying at James Corden’s house near Palm Springs during filming, and so they were able to be alone and keep their relationship very secret. 

‘So everyone was really surprised — and rather delighted — when Harry brought Olivia as his date to the wedding, and introduced her as his girlfriend.’

Olivia is best known for her role as Remy ‘Thirteen’ Hadley in House, as well as starring in The OC, and Tron: Legacy.

She received critical acclaim in 2019 for her directorial debut, the award-winning comedy Booksmart. 

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