Olivia Wilde Dating History: Before Split With Harry Styles, She Was Once Engaged to Jason Sudeikis and Married to Italian Filmmaker

Actress Olivia Wilde was married to Italian-American filmmaker Tao Ruspoli from 2003 to 2011. In a 2013 Marie Claire interview, Wilde talked about the lessons she learned from heartbreak.

"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," Wilde said.

The "Booksmart" director noted that she appreciated the suffering and sadness as it gave her the strength to go. She continued by saying that her split with Ruspoli has introduced her to the great love of her life, referring to Jason Sudeikis, Page Six reported.

Olivia Wilde Dating History: From Tao Ruspoli to Harry Styles

Before dating Jason Sudeikis for nine years and subsequently Harry Styles, Olivia Wilde was associated with three other celebrities.

Tao Ruspoli

Tao Ruspoli met Olivia Wilde when she was 18 and had just moved from Washington, D.C. to Los Angeles to become an actress. According to Wilde, she and Ruspoli met during the invasion of Iraq, and both of her parents were journalists who frequently covered conflict zones.

Her parents were ecstatic for her and informed her that tying the knot with Ruspoli was a bright spot in an otherwise bleak chapter of her life. They were married for eight years.

Ryan Gosling

In 2011, the same year Olivia Wilde and Tao Ruspoli officially split up, rumors of a romance between the actress and Ryan Gosling began to circulate. According to People, the two were seen out on a brunch date in February of the same year while Gosling was filming "The Ides of March" in Cincinnati.

Justin Timberlake

Following her supposed hookup with Ryan Gosling, Olivia Wilde was spotted at a Hollywood club in April 2011 with her "In Time" co-star Justin Timberlake. However, an insider told People at the time that they were just friends.

Bradley Cooper

A source told Us Weekly in June 2011 that Bradley Cooper and Olivia Wilde were "definitely hooking up." According to the site, they met when Wilde tried out for a part in "Limitless" and then later reconnected in the wake of their breakups.

Wilde filed for divorce from Ruspoli earlier that year, while Cooper and Renee Zellweger just ended their two-year relationship. However, Wilde and Cooper reportedly hooked up only for a few months.

Jason Sudeikis

In November 2011, Olivia Wilde and Jason Sudeikis started dating, and by January 2013, they were engaged. Wilde and Sudeikis eventually became proud parents of son Otis in 2014 and daughter Daisy in 2016.

In late 2020, reports of a broken engagement between Sudeikis and Wilde began circulating. However, since news of the breakup went public, the actors have been routinely spotted hugging one other, suggesting they have the best split in Hollywood.

Harry Styles

In January 2021, Olivia Wilde and Harry Styles announced their engagement after being photographed holding hands at Styles' agent's wedding in California. They first connected while working together on the production of Wilde's movie "Don't Worry Darling."

The couple "had chemistry almost instantaneously" when they first met on the set, a source earlier claimed. But after more than two years together, the pair decided to call it quits, according to numerous sources.

Sources close to the pair told People earlier this week that the couple is "taking a break," and it was "a very amicable decision." A source said Styles is still touring and is now going abroad, while Wilde is focusing on her children and her work in Los Angeles.

Another insider noted that Styles and Wilde are still "very close friends." Another friend told the outlet that Olivia Wilde and Harry Styles have "different priorities that are keeping them apart."

This article is owned by Latin Post.

Written by: Bert Hoover

Watch: Harry Styles and Olivia Wilde Taking a Break After Nearly 2 Years - From E! News