Olivia Wildes Struggles Post Harry Styles Breakup

When stepped out at the San Francisco International Film Festival this week, the Hollywood star sparked some concern among fans.

Not just because a looking markedly slimmer than years past, but also due to the fact her ex-boyfriend , 32, is rumored to be engaged to actress after a whirlwind eight months of dating.

As Kravitz, 37, was photographed with an on her finger, all eyes were immediately turned to Wilde, 42, whose two-year relationship with the former member was the subject of wild headlines and an .

Nearly four years since their split, Wilde seemingly put on a brave face as she promoted her upcoming directorial feature, The Invite, at the film festival on April 24.

But according to a source who spoke exclusively to the Daily Mail, the mother of two has not forgotten how 'painful' her breakup with Styles truly was. However, both Wilde and Styles have since happily 'moved on' from the rollercoaster romance, they said.

'When Harry and Olivia split, it was the hardest breakup he had ever gone through,' the source told the Daily Mail.

'He recorded an entire album about what he was going through, but it never saw the light of day. He decided it was best to keep it private and move on,' the source continued.

'Now that he's met Zoe, he is so happy and it all makes sense why he went through that.'

They added, 'The breakup with Harry was very painful for Olivia too, but she's dated other people and has moved on.'

Wilde sparked conversation this week when a clip from the San Francisco International Film Festival looking wide-eyed and gaunt.

Some critics took the opportunity to lash out against Hollywood's beauty standards and the influx of  for weight loss. 

However, defenders suggested the distorted look was actually due to the camera angle of the video.

Despite the confusion surrounding Wilde's recent appearance, the source explained to the Daily Mail how the actress doesn't take such speculation lightly.

'Olivia has always been a bit insecure and she cares what people think about her. Everyone does and just because she's famous, she's no different,' they said.

Her nearly two-year romance with Styles has received renewed attention after Page Six reported last week that Styles and Kravitz are engaged, and that he is 'completely smitten' with Kravitz.

Styles famously met Wilde while working on her second directorial feature, Don't Worry Darling, in late 2020. 

In November that year, it was reported that Wilde had ended her engagement to Saturday Night Live Alum Jason Sudeikis, 50, after nine years together.

The former couple share son Otis Alexander, 12, and daughter Daisy Josephine, nine.

Wilde and Styles first sparked romance speculation after they were seen holding hands at his manager Jeffrey Azoff's wedding in Montecito, California, in January 2021. 

However, the outing caused quite a frenzy among Styles' devoted fanbase, who pointed out their 10-year age gap and fueled rumors Wilde had cheated on Sudeikis while filming Don't Worry Darling.

The actress later shut down the cheating allegations in an interview with Vanity Fair.

'The complete horses**t idea that I left Jason for Harry is completely inaccurate,' she told the magazine in September 2022, insisting that their 'relationship was over long before' she met Styles on the set.

'Like any relationship that ends, it doesn't end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic.'

But that didn't stop the increased speculation into their relationship.

Wilde and Styles' rumored romance began to heat up throughout 2021 and into 2022. By February 2021, it was reported that Wilde and Styles had been living together in his Los Angeles home, as she was pictured moving some belongings into his home that Valentine's Day.

They were seen vacationing in Italy that summer, sharing a passionate kiss on a yacht in Monte Argentario. Wilde was also spotted supporting Styles at a Love on Tour concert stop in Las Vegas that September, and even sported a Love on Tour t-shirt two months later.

It was reported in December 2021 that Styles was 'slowly' getting to know Wilde's two children, and the singer even mentioned to Rolling Stone the following August that he was thinking more seriously about having kids of his own.

While the pair kept many details about their relationship private, fans did speculate that the lyrics to his single As It Was – released in April 2022 – were about the actress, as Styles sings: 'I don't wanna talk about the way that it was, leave America, two kids follow her, I don't wanna talk about who's doin' it first.'

Styles also spoke about protecting his relationships from the public, telling Rolling Stone: 'There's always going to be a version of a narrative, and I think I just decided I wasn't going to spend the time trying to correct it or redirect it in some way.'

Meanwhile, Wilde echoed their desire to protect their relationship in an interview with Variety.

'I'm not going to say anything about it because I've never seen a relationship benefit from being dragged into the public arena,' she said in August 2022. 'We both go out of our way to protect our relationship; I think it's out of experience, but also just out of deep love.'

Don't Worry Darling hit theaters in September 2022, but the release of the film was largely overshadowed by off-screen drama.

While promoting the film at CinemaCon in Las Vegas in April 2022, Wilde was handed a mysterious envelope marked 'Personal and Confidential' by a woman in the audience.

It was revealed that the envelope contained legal papers served by Sudeikis regarding their two children, a move that Wilde told Vanity Fair she was 'deeply saddened' and 'disturbed' by.

A representative for Sudeikis later said in a statement that the actor 'had no prior knowledge' his ex would be given the custody papers so publicly, and he 'would never condone her being served in such an inappropriate manner.'

Her breakup from Sudiekis made even further headlines when their former nanny shared intimate details about the celebrity couple's split in an , describing how Sudeikis was left heartbroken and Wilde was besotted with Styles.

She further claimed that Sudeikis became infuriated after seeing Wilde prepare a salad for Styles with her 'special dressing' in the family kitchen, leaving him ranting furiously at her, before he tried to prevent her leaving by lying under the car.

At the time, Wilde and Sudeikis shared in a joint statement to the Daily Mail: 'As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make such false and scurrilous accusations about us publicly.

'Her now 18-month-long campaign of harassing us, as well as loved ones, close friends and colleagues, has reached its unfortunate apex.

'We will continue to focus on raising and protecting our children with the sincere hope that she will now choose to leave our family alone.'

The former couple's nanny later filed a wrongful termination lawsuit against them in February 2023, alleging in her filing that she was put in the middle of the celebrity couple's split. 

In August that year, a judge . 

Representatives for Wilde and Sudeikis later declared in a statement to the Daily Mail that the 'lawsuit [had] been fully dismissed.'

'Both Olivia and Jason are hopeful they can finally close this chapter after what has not only been a selfish grab for financial gain, but a shameless exploitation of their trust played out in the media,' they said.

In September 2023, the former couple their custody battle, with the Ted Lasso actor agreeing to pay $27,500 in monthly child support for their two children, according to court documents obtained by the Daily Mail.

The exes agreed to share joint custody of their son Otis and daughter Daisy on a 'week-on, week-off basis.'

As Wilde's bitter custody battle played out in the public, her relationship with Styles appeared to run its course. 

In November 2022, it was from their relationship, as Styles resumed his world tour and Wilde remained in Los Angeles.

Although they appeared to press pause on their relationship, it soon became clear that Styles and Wilde had gone their separate ways when the singer became romantically linked to actress Taylor Russell in June 2023.

Since then, Styles has sparked romance rumors with model Emily Ratajkowski, singer Olivia Dean and producer Ella Kenny. 

By August 2025, he was speculated to be dating Kravitz after the two were frequently photographed together throughout Europe and New York.

As for Wilde, it seems that her co-parenting relationship with Sudeikis has turned a positive corner in recent years.

Just days after news of Styles' rumored engagement surfaced, Wilde in Los Angeles. She was seen dropping her children off with Sudeikis, as the two shared a hug.

Two years after her split from Styles, the director also sparked romance speculation with former basketball player Dane DiLiegro. Wilde is now reportedly dating British art dealer Caspar Jopling, to whom she was first linked in September 2025.

Representatives for Wilde declined to comment to the Daily Mail.