Olivia Wilde's relationships famously blew up in her face. Now insiders reveal deepest fear pushing her in 'sexualized' direction… and sad truth etched into her own name

Olivia Wilde's latest film opens with a quote from one of her heroes, her namesake, Oscar.

'One should always be in love,' wrote the Victorian playwright whose last name a young Olivia Cockburn assumed. 'That's the reason why one should never marry.'

It's a classic Wilde line – Olivia and Oscar: witty, sexy, defiant. And perhaps just a little bit sad.

Indeed, a source tells the Daily Mail, the actress and director is navigating a challenging time. 'Getting older and getting nearer what some might see as a midlife crisis is definitely something that has been crossing Olivia's mind,' the source said, noting that her recent headline-grabbing roles have coincided with a turbulent time in her private life.

Wilde separated from the father of her two children, Jason Sudeikis, early in the pandemic and then embarked on a two-year relationship with Harry Styles, a decade her junior.

The fallout from both relationships was bruising. But Wilde, 42, is not about to stop any time soon.

A member of the celebrated Cockburn journalistic clan, whose globe-trotting documentarian parents instilled in her a horror of being 'boring' – Wilde has coped by taking on increasingly provocative roles.

The Invite, which she directed and in which she stars, opens with that Oscar Wilde quote and follows the unravelling of a relationship during a night in which she and her husband, played by Seth Rogen, explore swinging with their uninhibited upstairs neighbors, played by Penelope Cruz and Edward Norton.

Her follow up, later this month, is I Want Your Sex, directed by Gregg Araki, in which she stars as a dominatrix – whips, chains and all.

'Olivia has wanted to explore these recent sensual roles for a while now,' the source said. 'Losing her relationships with Jason and Harry was very rough for her, so to reclaim her sexuality, and reclaim her self-worth, has been important. To play these characters on film has been therapeutic.'

Certainly, Wilde can be forgiven for seeking out ways to escape on camera from the behind-the-scenes drama.

The upheaval began when Wilde and Sudeikis separated after almost a decade together.

The pair weren't married – at the age of 19 she had eloped from Burning Man and married Italian American filmmaker Tao Ruspoli; an eight-year union she later termed 'romantic and insane.'

She and Sudeikis, 50, were engaged but never tied the knot and raised two children together: 12-year-old son, Otis, and nine-year-old daughter, Daisy.

Their separation was initially amicable, until it came to the question of custody of the children. Sudeikis wanted them to be raised in New York; Wilde wanted them in Los Angeles.

So acrimonious was the spat that a court official served her with legal papers while she was on stage in April 2022, in Las Vegas, promoting Don't Worry Darling.

She jokingly asked the process server whether the brown envelope was a script.

On reading it, Wilde ignored the contents and carried on, but she later said it was deeply distressing.

'It was my workplace,' she told Variety four months after the event. 'In any other workplace, it would be seen as an attack. It was really upsetting. It shouldn't have been able to happen. There was a huge breach in security, which is really scary.'

Time, it seems, has done little to diminish the sting of that moment. Just this week Wilde appeared on Alex Cooper's podcast, Call Her Daddy, and recalled it as 'incredibly traumatizing.'

'But I get through it. Because weirdly as women we are taught to muscle through the most insane experiences, so I was like: just finish your speech.

'Got through it. Went backstage and completely dissolved into a puddle. Then I was like, no one saw it because there's no phones allowed. Oh, what's that? It's already up on Page Six? There's a video? Oh, well no one is going to look because no one is paying attention.

'And a couple of months later, I met Tom Cruise, and he was like, 'Hi, I'm Tom. F***** up what happened to you in Vegas.''

Getting served on stage was a surreal low point in what proved to be, for Wilde, a torrid publicity tour.

While discussing Don't Worry Darling, over the course of several months, she was questioned repeatedly about why Shia LaBeouf, originally cast as the male lead, was replaced.

His role was ultimately taken by Styles, 32. Wilde said that LaBeouf's 'combative' approach did not work for her, and made her leading lady, Florence Pugh, uncomfortable.

LaBeouf hit back, insisting he quit due to a lack of sufficient rehearsals, and releasing text and video messages including one in which Wilde told LaBeouf that the testing time 'might be a bit of a wake-up call for Miss Flo.'

Pugh made little effort to hide her fury at the insult, spurning the September 2022 Venice Film Festival press conference (she insisted it was due to a clash with filming Dune: Part Two) and posing separately from Wilde at a New York City premiere.

Wilde, meanwhile, continued praising Pugh's 'astonishing' work on the film and tried to downplay rumors of on-set rifts.

It didn't help that, after the tornado had passed, Wilde and Styles went public with their burgeoning romantic relationship. Rumors immediately flurried that this too had been a source of tension between Pugh and her director.

But though Wilde tried to settle into some form of normalcy with Styles their schedules strained the relationship and, by November 2022, it was all over: the film and the shrapnel it had sprayed; the relationship with Styles; the life with Sudeikis she once knew.

'I don't think you know what you're made of until you fall apart,' Wilde told The Cut last month. 'I don't trust anyone who hasn't had their heart broken. If you can push through the moment, you have previously identified as the worst possible thing that could happen to you, whether that is divorce or the internet hating you or whatever, you are forged into something way better than you could have possibly imagined.'

Wilde said she took time to read and journal, drive to Big Sur, climb mountains in Bhutan and explore Ireland and Hawaii.

'I tell my female friends to take themselves on road trips,' she told the magazine. 'You meet strangers. You introduce yourself as who you are.'

The break revived her, and soon she was back in business and directing her third film, The Invite.

Since September, Wilde has been in a relationship with art world scion Caspar Jopling, the 34-year-old ex-husband of singer Ellie Goulding.

'I'm in a really lovely relationship now,' she told The Cut. 'I adore him, and I feel completely whole and intact as a person. I think it's only possible after spending a couple years alone. If you haven't ever been single for a few years, how do you even know who you are?'

At the Sundance Film Festival in January, she had The Invite and I Want Your Sex to promote: both films were rapturously received and the subject of bidding wars.

Then in May, while appearing at the San Francisco International Film Festival, a picture emerged of Wilde, hollow-cheeked and wide-eyed, seemingly painfully thin to the point where she drew comparisons to Gollum from Lord of the Rings.

The image became an internet meme. It didn't help that Styles, two years into his relationship with Zoe Kravitz, 37, had apparently just popped the question. Speculation swirled that Wilde was left reeling by the 'blow' after Kravitz was pictured wearing a $1million rock on her ring finger.

For her part, Wilde laughed it off – as did those close to her.

Her brother Charlie asked in an Instagram story she shared: 'Olivia Wilde, do you care to address recent rumors that you're a resurrected corpse?' A giggling Wilde replied that she was 'not dead.'

Indeed, she is not. In fact, our source tells us, the only thing Wilde is interested in resurrecting is her sense of self. Taking on challenging movie roles is, the source said: 'About making her feel sexier and that she's still got it. If it works on film, then it can work in real life.'

Certainly, it's working on film. The Invite opened in late June to a strong box office performance and currently has a 97 percent rating on Rotten Tomatoes.

I Want Your Sex had its LA premiere on Tuesday night, with Wilde beaming alongside co-star Cooper Hoffman – son of Philip Seymour Hoffman.

Daily Mail has reached out to Wilde's representatives for comment. 

Whatever it is that is now propelling Wilde, it's working. And, the source said, it has emboldened her.

'She's looking to push the envelope even more in coming years and tackle other sexualized roles, to return to the woman she has always thought she has been,' the source said.

'She may have lost her way with how her relationships have blown up in her face, but these roles have given her a new lease on life. It's made her feel so much better about herself.'