Inside Olivia Wilde's murky dating history... from her messy Jason Sudeikis divorce to the Harry Styles drama
Inside Olivia Wilde's murky dating history... from her messy Jason Sudeikis divorce 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.
![[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]](https://i.dailymail.co.uk/1s/2025/01/28/19/94606627-14333805-image-a-97_1738093986722.jpg)
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.
![[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]](https://i.dailymail.co.uk/1s/2025/01/28/18/94605993-14333805-image-a-43_1738087550304.jpg)
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.
![[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]](https://i.dailymail.co.uk/1s/2025/01/29/15/94605991-14333805-In_February_2011_news_hit_the_web_that_Olivia_and_Tao_who_was_th-a-4_1738165353070.jpg)
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.
![[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']](https://i.dailymail.co.uk/1s/2025/01/29/15/94605995-14333805-Olivia_seen_with_Tao_in_2009_admitted_that_the_split_was_difficu-a-1_1738165352993.jpg)
