A Complete Timeline of Olivia Wilde Relationships Over the Years

Inside Olivia Wilde's star-studded romantic history: The actress-turned-director is a mother to two!  

A highly-sought A-list actress and a quickly soaring filmmaker, Olivia Wilde has ostensibly outshined her peers in a short span of time. She delved into acting in the early 2000s with roles in Skin, The O.C., Year One, and a myriad more in the decade to come.  

But it wasn't until Wilde made her directorial debut, Booksmart, in 2019, that the world started viewing her as an imposing Hollywood figure. Wilde's star-studded love life and her occasional feuds with fellow A-listers have also made a recurring name in the media.  

Inside Olivia Wilde's Dating History!   

Wilde's romantic associations with fellow A-listers have been a staple in the gossip tabloids for a while now. The Don't Worry Darling director has gone from getting married early in her career, courting the most eligible bachelor, and embracing motherhood with a longtime partner, to revealing the most surprising love affair of the decade.   

Wilde's earliest known romance was with filmmaker Tao Ruspoli, who she married in 2003. Wilde acknowledges the growth her marriage with Tao endowed her. The actress also explains how the two drifted apart and the relationship ran its course. 

"I hung on for as long as possible until it was more hurtful to stay," said Wilde, who filed for divorce from Ruspoli in 2011. The Booksmart director jumped right into the dating pool after her divorce. And in the next few months, Olivia was linked with a number of famous faces.   

Wilde sparked dating rumors with Ryan Gosling, Justin Timberlake, and Bradley Cooper, but the rumors were later chalked out as casual flings. Wilde kicked off her most notable relationship in 2011. She was linked with actor Jason Sudeikis in November 2011.  

Wilde and Sudeikis were soon a young Hollywood power couple. The twosome even announced their engagement in 2013 and went on to welcome two kids. The couple practically lived a married life but never actually exchanged their vows.  

Despite the media's inundated curiosity and speculations about their long engagement, Wilde and Sudeikis reported no trouble in their paradise. The duo's separation announcement came as quite a shock in late 2020. An insider said the pair had transitioned from being romantic partners to co-parents.   

Wilde and Sudeikis's split is one of the most amicable Hollywood splits. Sure, the estranged duo had their moments of feud and disdain in the beginning. But the pair have since come out stronger as friends and parents. The Don't Worry Darling star and her ex are often spotted on cordial meet-ups.  

Who is Olivia Wilde Dating?  

A recently surfaced rumor indicates that the Booksmart director is dating again. And the linked beau with none other than Wilde's last famous ex, Harry Styles. An eagle-eyed fan noticed Wilde spotting an old T-shirt of Styles and the rumors have been swirling nonstop since.   

Olivia and the former One Direction star ended things in November 2022. Hence, it's not much of a surprise if the A-list pair have indeed decided to rekindle their romance. Olivia's relationship with Harry has to be the most surprising yet fan-favorite pairing of the decade. The duo was first linked in early 2021.  

Wilde, who is ten years older than the singer-turned-actor, had cast Harry in her directorial, Don't Worry Darling, to play Florence Pugh's husband, late in 2020. The duo's budding romance was made official by an insider early on. But the journey ahead was as exciting as it was overwhelming for the unlikely couple. 

Although Olivia and Styles never made their relationship official on Instagram, the duo often hinted at their growing love for each other. The One Direction alum even hinted at his love for Wilde in his hitmaker, As It Was. Fans were certain that Styles' lyrics, "Leave America, two kids follow her," were about his wishful situation with Wilde.  

While Olivia and the Grammy-winning singer kept their relationship on the low from their side, insiders still kept fans updated on where the duo was as a couple in a highly scrutinized romance. "They're not nervous about spending time apart," a source said while referring to both Harry and Wilde's soaring careers, and busy schedules.  

The source added, "It adds to the attraction when they reunite after some time off." Wilde and Harry's romance seemingly hit a bump in late 2022; when Wilde's former nanny claimed that the Life Itself actress had cheated on her Sudeikis with Harry.    

The pair were first linked in early 2021! 

More allegations followed from the anonymous nanny, which probably strained Wilde's romance with Styles. The twosome's breakup announcement came shortly after the drama in November 2022. An insider said that the duo decided it was in their best interest to go separate ways.  

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