Inside Olivia Wilde's murky dating history... from her messy Jason Sudeikis split to the Harry Styles drama

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After two explosive and very-public splits, an array of cheating allegations, and a two-year-long custody battle that continuously dominated headlines, Olivia Wilde is taking a different approach with her new relationship with basketball star Dane Diliegro.

The two stars were spotted cozying up at a Los Angeles Lakers game last week, and a source told DailyMail.com afterwards that the actress, 40, is determined to keep her latest romance more 'private' because she really wants this one to 'last.' 

The House star has certainly had a tumultuous journey to finding love.

Back in 2021, her personal life was fiercely picked apart by the world after it was revealed that she was dating Harry Styles, just months after she had split from her partner of 10 years, Jason Sudeikis.

At the time, rumors erupted that she had an affair with the One Direction member - who is 10 years younger than her - which were only heightened after her former nanny made a series of explosive claims about their split; Olivia has since denied that she was unfaithful to Jason.

Even so, her and Harry's romance was certainly controversial. On top of the swirling allegations that she had cheated on Jason with the singer, there was also speculation that their romance had caused serious 'tension' on the set of her psychological thriller Don't Worry Darling.

Harry and Olivia fell in love while they were making the film - which she directed and they both starred in, alongside Florence Pugh and Chris Pine - and it was reported that some cast members were put off by their romance.

When it came time for the film's premiere at the Venice Film Festival, things seemed immensely icy between Olivia and Florence on the red carpet.

After two explosive and very-public splits, Olivia Wilde has now been linked to basketball star Dane Diliegro

As her new romance kicks off, FEMAIL has recapped Olivia's rollercoaster ride dating history from start to finish. She's seen left with Harry Styles and right with Jason Sudeikis

There was also the now-infamous rumor that Harry spat on Chris during the event, resulting in a immense speculation that the entire cast was feuding with a barrage of articles and social media posts about the alleged drama. 

Olivia did her best to shut these rumors down, stating in an interview that she had 'nothing against Florence for any reason.' 

All the while, she also became embroiled in a nasty custody battle with her ex Jason over their two kids.

It was definitely a wild ride, and it all played out in front of the entire world to see. 

But it wasn't the first time the star - who eventually split from Harry after nearly two years in November 2022 - endured a very-public breakup, as she was actually previously married to an Italian filmmaker and the son of a prince, Tao Ruspoli.

Their relationship had its own fair share of wild twists and turns before they divorced in 2011.

And after that, Olivia was linked to a slew of famous faces including Ryan Gosling, Justin Timberlake, and Bradley Cooper - before she ultimately started dating Jason.

Now, Olivia has a new love in her life, and she is reportedly determined to avoid making the same 'mistakes' from her past after her previous relationship became a 'public spectacle' and after years of seeing her personal life in headlines.

Only time will tell if Olivia will finally get her happily ever after, but as her new romance kicks off, FEMAIL has recapped her rollercoaster ride dating history from start to finish.

From her and Jason's messy split and her controversial relationship with Harry to her marriage at only 19 years old and latest partner, here's a look back at everyone Olivia has dated.

Tao Ruspoli

Olivia met Italian filmmaker Tao Ruspoli (seen in 2009) at the Burning Man festival in 2002. After a whirlwind romance, the two eloped months later, when she was only 19 years old

Olivia met Italian filmmaker Tao at the Burning Man festival in 2002, when she was just starting off as an actress.

After a whirlwind romance, the two eloped months later, when she was only 19 years old. The pair married on a school bus, with just a couple of witnesses. 

She later recalled thinking during their unconventional wedding, 'Hey, isn't this an optimistic thing to do? And if it lasts, we're lucky.' 

In February 2011, news hit the web that Olivia and Tao, who was the son of an Italian prince, were getting a divorce after eight years of marriage.

'They have been living apart after trying for quite some time to make their relationship work,' a source told People at the time.

Olivia admitted to Marie Claire that the split was difficult for her, confessing in August 2011, 'The trauma of the whole thing has been humbling and for the first time, I'm a little bit wobbly.'

But the pair were spotted getting cozy again later that month, sparking rumors of a reconciliation.

Photographers caught them enjoying an intimate lunch together, and at one point, Tao was seen feeding Olivia food off his fork.

In February 2011, news hit the web that Olivia and Tao, who was the son of an Italian prince, were getting a divorce after eight years of marriage. They're seen in 2009

Olivia (seen with Tao in 2009) admitted that the split was difficult for her, confessing, 'The trauma of the whole thing has been humbling and for the first time, I'm a little bit wobbly'

Even so, the divorce was finalized in October 2011 and the couple were not spotted together again after that.

Oliva reflected on the romance a few years later to Marie Claire, explaining, 'I had grown up with Tao.

'We had just drifted. I felt I had something to prove. If you fall off a horse, you get back up. 

'I am not a quitter. I hung on for as long as possible, until it was more hurtful to stay.'

'I'm so grateful for the pain and the heartbreak. It gave me the courage to leave and brought me to the great love of my life,' she added of her then-partner, Jason.

Ryan Gosling

Olivia and Ryan Gosling were seen getting flirty at the Golden Globes in January 2011. They're pictured at the event

And soon after she announced her split from Tao, Olivia and Ryan were spotted on a series of dates together. But things seemed to fizzle out soon after. They're seen at the Golden Globes

Olivia and Ryan were seen getting flirty at the Golden Globes in January 2011.

Photos showed them laughing together and him intimately whispering in her ear during the event.

And soon after she announced her split from Tao, Olivia and Ryan were spotted on a series of dates together.

In March 2011, they seemed to confirm that they were dating when they were caught holding hands at an aquarium in Kentucky.

However, it must have fizzled out soon after because that was the last the public heard of their romance.

Justin Timberlake

In April 2011, rumors erupted that Olivia was dating Justin Timberlake after they were seen partying at a Hollywood nightclub together

In April 2011, rumors erupted that Olivia was dating Justin after they were seen partying at a Hollywood nightclub together.

Olivia and Justin, who was on a break from his on-and-off-again relationship with Jessica Biel, were said to have been 'dancing all night' together. 

An onlooker told Us Weekly at the time that they looked like a 'couple' and that it was 'obvious' it was 'a date.' 

'They were dancing, whispering, he had his hand on her back and shoulders and they were together all night,' they said.

'His arm was around her, they were talking closely, just the two of them. Justin and Olivia were there with a group, but weren't talking to anyone else.' 

But Olivia, who had appeared in the film In Time with Justin, was quick to shut down the speculation.

But Olivia, who had appeared in the film In Time with Justin (seen together in 2007), was quick to shut down the speculation. She said, 'We're just friends and have been for years'

She tweeted, 'Cool it, honeybadgers. We are just friends and have been for years.' 

One month later, the actress spoke about dating again following her split from Tao.

'I am opening my heart up to the idea of dating,' she told Glamour. 'But things have changed a lot since I was dating in high school.'

When asked if she thought she would get into another serious relationship soon, she remarked: 'I don't want to but I probably will.

'I wish I could play the field but it's so not me. I go 100 percent into everything and I'm a really good girlfriend.'

'I've been lucky to have chemistry with my costars,' she added, seemingly referring to the Justin rumors.

'I really enjoy pretend kissing. If you're pretending to love each other you have to find something to fall in love with.'

Bradley Cooper

Olivia was briefly linked to Bradley Cooper in May 2011 after they were seen getting flirty at an after party for the premiere of his flick Hangover II. They're seen together in 2019

Olivia was briefly linked to Bradley in May 2011 after they were seen getting flirty at an after party for the premiere of his flick The Hangover Part II.

The House star, who is almost a decade younger than the A Star Is Born alum, was seen embracing Bradley at the event. 

The pair spent the night chatting away in a private booth. At one point, Olivia put her arm around Bradley and at another, she gently touched his knee. 

Life & Style even reported that the pair left together afterwards. 

A source told the publication, 'Olivia was Bradley's date. He was always taking her hand or putting his hand on her lower back, it was really sweet. He took care of her all night.'

One month later, a separate insider told Us Weekly that the two stars were 'definitely hooking up.' 

But her rep insisted, 'Olivia is single and not dating Bradley.' 

Jason Sudeikis

Olivia's romance with Jason kicked off in November 2011, and Jason proposed two years later in 2013. They're seen in November 2014

Olivia's romance with Jason kicked off in November 2011, months after they met at a Saturday Night Live wrap party.

During a 2017 appearance on The Late Late Show With Stephen Colbert, the Horrible Bosses star spilled on his first interaction with Olivia, and he explained that he had 'heard from the grapevine' that she was 'dating someone' so he 'didn't make any sort of moves' at the party.

The couple welcomed their first child, son Otis, in 2014, which followed by the birth of their daughter, Daisy, in 2016

'I actually came off looking a lot cooler than I really am because I had heard through the grapevine, mutual friends would report back, "Oh, you know, I think she's dating someone." So I didn't make any sort of moves,' he recalled. 

Olivia also once said of meeting Jason, 'I was just learning to be by myself. I'd been divorced nine months. We were both seeing people but were single. He seemed to really see me, see through the bulls**t.'

The actress told Allure that they 'kept running into each other' in the months that followed, before one of her friends finally gave them the push to get together. 

'[One night], my best guy friend walked up to him and said, "This is Olivia's number. Use it." That was the beginning,' she said.

The two went public with their romance that December, and Jason proposed two years later in 2013.

Olivia told Net-a-Porter in 2016, 'We're committed and promised... We are seriously connected.' They're seen together in 2018

But their relationship came to a screeching halt in 2020, soon after she began filming Don't Worry Darling with Harry. They're seen on set 

The couple welcomed their first child, son Otis, in 2014, which followed by the birth of their daughter, Daisy, in 2016. 

When asked about when they were still planning to get married by Net-a-Porter in 2016, Olivia explained that it wasn't a priority for them now that they had become parents.

'Before you have a child, marriage is the ultimate commitment and promise to one another, and then once you have a child, it's like, "Oh, we're committed and promised already,"' she explained. 'We are seriously connected.'

But their relationship came to a screeching halt in 2020, soon after she began filming Don't Worry Darling with Harry.

Production kicked off in September 2020, and two months later, it was revealed that she and Jason had gone their separate ways after 10 years together. 

Reports initially claimed that the split was 'amicable' and that they had quietly gone their separate ways 'at the beginning of the year.' 

But when the actress was spotted holding hands with the former One Direction member in January 2021, rumors started to swirl that she had cheated on her fiancé with the British superstar.

At the time a source told People, 'Jason feels that the timeline that Olivia and Harry would like people to believe - that she and Jason split ages ago, long before she became involved with Harry - is simply not accurate.

Production kicked off in September 2020, and two months later, it was revealed that she and Jason had gone their separate ways after 10 years together. Olivia and Harry are seen on set 

When the actress was spotted holding hands with the former One Direction member in January 2021, rumors started to swirl that she had cheated on her fiancé with the British superstar 

'She began filming [Don't Worry Darling] in September, and by October, he began to get the impression that she wanted out. By November, they'd announced their split.' 

Olivia has repeatedly denied that she was unfaithful to Jason and has insisted that she and Jason split before she started dating Harry. 

'The complete horses**t idea that I left Jason for Harry is completely inaccurate,' she told Vanity Fair. 

Amidst the messy split, Olivia and Jason soon became embroiled in a nasty custody battle over their two children. 

The actress was infamously served custody papers on stage while at CinemaCon in April 2022. 

She later spoke of the incident to Variety, stating, 'To try to sabotage [me], that was really vicious... 

'But, you know, sadly, it was not something that was entirely surprising to me. I mean, there's a reason I left that relationship.'

The custody battle began after Olivia allegedly told Jason that she wanted to move the kids to London, where Harry lived. 

According to court documents, Olivia and Jason had initially agreed to send their kids back to school in Los Angeles for the 2022 school year, after filming on Ted Lasso wrapped. 

Olivia has repeatedly denied that she was unfaithful to Jason. 'The complete horses**t idea that I left Jason for Harry is completely inaccurate,' she told Vanity Fair. They're seen in 2019

Amidst the messy split, Olivia and Jason soon became embroiled in a nasty custody battle over their two children. The family is seen in 2018

The actress was infamously served custody papers on stage while at CinemaCon in April 2022 (seen)

However, he claimed in the documents that Olivia told him that she 'intended to relocate with the children to London following the close of school in 2023.'

He wanted to move the children to New York instead, claiming that he and Olivia were largely based in New York for most of their relationship.

The pair ultimately settled their custody case in private in September 2023, after a lengthy court battle that spanned two years. They're seen in 2020

She fired back by asking for a motion to dismiss his lawsuit and filing a petition to 'determine parental relationship' in California instead, claiming that the children spent most of their last fours years in LA or in London, and not New York. 

Amidst the messy legal drama, the couple's former nanny made a series of bombshell accusations about the pair exclusively to DailyMail.com.

She sensationally claimed that Olivia was talking of marriage with Jason just one month before she dumped him.

She also alleged that Jason became so infuriated after he saw Olivia had prepared a salad with her 'special salad dressing' for Harry that he flung himself under her vehicle in a desperate bid to prevent her from visiting the musician.

Olivia and Jason hit back at their former employee's allegations in a joint statement, saying: '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.' 

The pair ultimately settled their custody case in private in September 2023, after a lengthy court battle that spanned two years. 

The stars agreed to share joint custody and the actor now pays $27,500 in monthly child support for their two children.

Harry Styles

Olivia and Harry confirmed their controversial romance when they held hands at his manager Jeff Azoff's wedding in January 2021. They're seen on set of Don't Worry Darling

The pair seemed undeterred amidst the ongoing scrutiny surrounding their romance. They're seen in March 2022 

Olivia and Harry confirmed their controversial romance when they held hands at his manager Jeff Azoff's wedding in January 2021.

By July, they were flaunting their love to the world when they were seen kissing passionately on a yacht in Italy together.

And in December of that year, it was reported that Harry was 'getting to know her kids.'

The pair seemed undeterred amidst the ongoing scrutiny surrounding their romance.

But their relationship found itself in more hot water in September 2022 when they attended the Venice Film Festival premiere of Don't Worry Darling.

At the event, things seemed extremely icy between Olivia and their costar Florence, who noticeably skipped the press conference before hand.

At the time, all eyes were on Harry and Olivia as a source told DailyMail.com that it was their romance that had caused the 'tension' on set.

'Harry and Olivia started spending more time together - sneaking off for coffees, hanging out in one another’s trailers, and sharing small, routine intimacies,' they explained. 

In September 2022, they attended the Venice Film Festival premiere of Don't Worry Darling but things seemed extremely icy between Olivia and their costar Florence

At the time, all eyes were on Harry and Olivia as a source told DailyMail.com that it was their romance that had caused the 'tension' on set. Harry and Florence are seen in the film 

'It was clear to all they had a real connection. When they were pictured holding hands for the first time, Florence wasn’t too happy.

'There was already tension between the two women and this undoubtedly fanned the flames.' 

Two months later, People reported that Harry and Olivia were 'taking a break,' despite the fact that she was seen attending his concert with her kids days prior. They're seen in April 2022

An insider also told Vulture that Olivia and Florence once got into a 'screaming match' over Olivia's 'frequent, unexplained absences' on set, during which she'd 'disappear' to spend time with Harry.

But Olivia continuously gushed over Florence amid their rumored feud, calling her 'sensational,' 'brave,' and a 'superhero' in numerous interviews while discussing the movie. 

'I have nothing but respect for Florence’s talent,' she said during an appearance on the Late Show. 'She’s fantastic. I have nothing against her for any reason.' 

There was also the now infamous rumor that Harry spit on Chris - which Chris later branded as a 'ridiculous' and 'complete fabrication.' 

Two months after the Venice Film Festival, People reported that Harry and Olivia were 'taking a break,' despite the fact that she was seen attending his concert with her kids days prior. 

'He's still touring and is now going abroad. She is focusing on her kids and her work in LA,' a source told the publication. 

'It's a very amicable decision. They're still very close friends.'

A second insider added, however, in a new report days later that the decision was 'difficult for Olivia,' hinting that it was Harry who had broken it off.

'They have had some issues, but Olivia thought they were gonna work through it all. She is disappointed. It's just a tricky situation, though,' they said. 

Dane DiLiegro

Flash forward two years and Olivia has now officially moved on with basketball star Dane 

Flash forward two years and Olivia has now officially moved on with basketball star Dane.

The two sparked relationship rumors when they were spotted cozying up while attending a Los Angeles Lakers game together earlier this month.

The brunette beauty was pictured gazing romantically at Dane, while he wrapped his arm around her shoulder.

And now, a source has confirmed that they're indeed dating exclusively to DailyMail.com.

The insider said Olivia has 'finally moved on from her breakup' with Harry, after taking time off from dating to 'focus on herself and her family.'

'After the Harry breakup, she really took time off dating and away from the spotlight to focus on herself and her family,' they said. 

'She got way too caught up in that and their relationship became a public spectacle.' 

They added that she is determined not to 'make this mistake ever again' and that she wants to keep this romance out of the spotlight as much as possible 'because she knows that's the only way something will last.'

The two sparked relationship rumors when they were spotted cozying up while attending a Los Angeles Lakers game together earlier this month 

She reportedly 'finds Dane incredibly attractive, and they have a lot in common.' 

'He is passionate and he knows how to treat a woman,' the insider continued. 'They both love sports. They enjoy being around each other and not afraid to show affection when they are out together.' 

A second insider added: 'She's dating and having fun. She's working non-stop so not looking for anything serious.' 

Olivia's new man is an actor and retired athlete, who previously played professional basketball for eight seasons for teams in Italy and Israel. 

Done, who is 6ft8, served as an apprentice under famed Tuscan butcher Dario Cecchini for multiple years.

He has also hosted his own travel series on YouTube and dabbled in acting, starring in American Horror Stories, Guardians of the Galaxy Vol. 3, Sweet Home, and the 2022 film Prey.