A Complete Timeline Of Olivia Wilde's Relationships

Actress, director, and filmmaker Olivia Wilde's dating life has been a hot topic of conversation over the last few years, especially with her having been linked to British pop star and actor Harry Styles in 2021 (via People). From her early marriage to an Italian prince to her very long engagement to a popular "Saturday Night Live" alum, to even bearing a child of her own, Wilde's successful acting career has almost always been accompanied by glamorous and high-profile relationships with in-demand entertainers and more.

There's absolutely no doubt that Wilde's personal life these days definitely seems to be going just as well as her impressive and storied career — but who has she dated in the past, and perhaps just as importantly, why did they break up? Continue reading to learn more about the details of Olivia Wilde's past and current relationships, from the low-key to the hot and heavy.

Olivia Wilde met Tao Ruspoli, a filmmaker and Italian prince, in 2003, and the couple eloped within six months. The pair married in Virginia when Wilde was just 19 years old. Speaking about the whirlwind romance, Wilde told Women's Health in 2008, "My dad did have a minor heart attack, and it was hard to imagine settling down at the time, but there was this wave of romantic excitement and an overwhelming sense that we were supposed to be family. We were very open to the idea that if it didn't work, we would let it go its course. No pressure."

Wilde and Ruspoli later collaborated on a film called "Fix," which was released in 2008 (via IMDb). Despite his royal title, Wilde often spoke of how her husband was not the conventional prince that people may have expected. She told Women's Health, "Everyone expects him to pick me up in a limo or a yacht," she says. "Then Tao rolls up in this old Thunderbird, wearing flip-flops, his hair all crazy. People are like, 'He's a prince?'"

In February 2011, a representative for Olivia Wilde and Tao Ruspoli publicly confirmed that the couple had separated, and a month later, Wilde filed for divorce citing irreconcilable differences (via People).

In 2013, Wilde told Marie Claire, 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." She added, "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."

Although Ruspoli did not speak about the divorce at the time, he released a documentary titled "Monogamish" in 2014 (via IMDb), in which he explained his state of mind during that time. Reading a letter, he said, "I'm in a state of total crisis. My wife has just left me after nearly 10 years together, and my whole world has crumbled." The documentary explored whether the concept of monogamy is natural and included interviews with a range of people discussing sex, relationships, and marriage (via ET Online).

As it would turn out, Olivia Wilde's "great love" was actor and comedian Jason Sudeikis (via Marie Claire). Reports of a romance between the two began to swirl in November 2011. The pair first met at a "Saturday Night Live" wrap party following the show's Season 36 finale, but the two did not officially begin dating until around six months later. During an interview with Stephen Colbert (per People), Sudeikis explained, "I was just very, very busy with other things. And next thing you know, I stopped being busy, she stopped dating someone, and then it was off to the races. We sort of reintroduced ourselves. The universe had more in store for us in the fall."

Once the couple finally did get together, they took the relationship slowly. Wilde told Howard Stern (via YouTube), "When he got my number, he didn't text me for a month. ... He literally didn't kiss me until the fourth date. He finally kissed me and I was completely head over heels."

Less than a year later, USA Today reported that Wilde and Sudeikis moved in together in Manhattan.

After just a year of dating, Olivia Wilde and Jason Sudeikis got engaged over the 2012 holidays and publicly announced the good news in January 2013 (via People). Sudeikis gushed about adoring Wilde's personality and good looks during an InStyle interview later that year. At the time, he said, "She is a combination of everything that I love about women — she's smart, strong, caring, beautiful, and as funny as anybody I've ever known. She just has it all."

Despite being engaged, the couple never set a date for a wedding. Wilde told Vanity Fair that she was looking forward to a long engagement and said, "It's funny, people tend to skip over the engagement thing. They think it's like, 'Oh, engaged.' And then you get there. I don't think you should spend your entire engagement planning a wedding. Because it's fun. It's this great time. It's like dating-plus."

In late 2012, Olivia Wilde spoke about how she saw herself becoming a mother in the future. She told USA Today, "My mom was a great example of having a professional life and having a kid. It can be done. No one is saying it's easy. But I'm totally inspired by the idea of being a badass working professional mom. I'm so into my dog. I can't imagine how I will smother my child."

By April 2014, Wilde and Jason Sudeikis welcomed their first child: a son named Otis Alexander. Wilde announced the birth on Twitter, joking, "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I'm the building)."

Two years later, in 2016, Wilde confirmed on Instagram that she was pregnant with the couple's second child. Alongside an adorable photo of her and Otis holding their stomachs, she wrote, "Matching baby bumps." Later that year, Wilde announced on Instagram that she and Sudeikis had welcomed their second child, a daughter named Daisy Josephine.

The world was devastated in November 2020 when it was announced that Olivia Wilde and Jason Sudekis had ended their relationship (via People). Hours after the split became public, People reported that Wilde posted a sweet photo of her two children on her Instagram Story alongside the caption "My everythings."

In August 2021, Sudeikis spoke about the breakup during an interview with GQ, and said, "I'll have a better understanding of why in a year," he said, "and an even better one in two, and an even greater one in five, and it'll go from being, you know, a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle." 

In April 2022, Wilde and Sudeikis were back in the headlines when Wilde was served with custody papers while she was speaking on stage at CinemaCon to promote her new film, "Don't Worry Darling" (via Page Six).

In January 2021, Olivia Wilde and former One Direction frontman Harry Styles broke the internet when they were seen arriving together and holding hands at manager Jeff Azoff's wedding in Montecito, California (via Page Six). The pair met on the set of "Don't Worry Darling," a film directed by Wilde and starring Styles, in September 2020.

Later in 2021, Page Six reported that the new couple was spotted vacationing together in Italy. Wilde was also seen dancing and singing at several of Styles' concerts (via the Metro).

In May 2022, Styles spoke with Howard Stern, who asked the young ingenue if he "fell in love" on the set of "Don't Worry Darling" (via People).

"Oh, wow, how to answer this question?" Styles replied. "I had a wonderful experience being directed by Olivia. I think there is something that obviously ... acting is very uncomfortable at times. I think you have to trust a lot. Being able to trust your director is a gift."

The couple was spotted on vacation in Italy again that same month (via Popsugar), apparently proving that the relationship is still going strong despite their various work commitments and Styles flying around the world on tour!