Olivia Wilde Has A History Of Age Gap Relationships—& Won't Apologize For It

All of the public relationships Olivia Wilde has been in involved a considerable age gap. And that was true even before she rose to prominence in the teen drama "The O.C." in the aughts. In late 2003, the "Tron: Legacy" actor tied the knot with an Italian man named Tao dei Principi Ruspoli, a marriage that earned Wilde the title of princess (though Italy had abolished the monarchy decades earlier, many members of the one-time royal family still use their titles). She was 19, whereas Ruspoli was going on 28. The two divorced in 2011, after eight years of marriage. 

In November of that same year, Wilde entered a relationship with Jason Sudeikis, with whom she had two children. She was 27, while he was 36. After nearly a decade together, Wilde and Sudeikis split in 2020. From then on, Wilde seemingly flipped the script, with her subsequent boyfriends being younger men. In 2021, Wilde was linked to Harry Styles after working together in her thriller "Don't Worry Darling." The pairing earned considerable public attention, particularly because Wilde was 37, and the One Direction alum was 27.

Wilde went from dating older men to being the older woman. As such, she became a first-hand witness to how the public reacts when an older woman dates younger men, as opposed to when an older man dates younger women. The public has had lots to say about Wilde's age-gap relationships, but she won't apologize for any of it. She was particularly struck by the outrage her relationship with the 10 years younger Harry Styles sparked online, which caught her by surprise. "We've done this to women for a long time. Why is it? I don't know. People were f***ing p***ed," she reflected on the "Call Her Daddy" podcast in June 2026.

Olivia Wilde believes Harry Styles' status among young women complicated things and made it impossible for her to show any happiness at all. "I would go to shows and dance, and people were like, 'You sl*t! How dare you dance and smile?'" she recalled. 

The relationship didn't last long, and by late 2022 Wilde and Styles had broken up. In her next relationship, she was again the older half. In 2025, Wilde was briefly linked to actor and former basketball player Dane DiLiegro, who is four years her junior. Later that year, the actor and director began dating British art dealer Caspar Jopling, Ellie Goulding's ex-husband, who is eight years Wilde's junior. After the end of her romance with Styles, Wilde also began to explore the dynamics in her work. In 2026, she starred in Gregg Araki's "I Want Your Sex," co-starring with the much-younger Cooper Hoffman.

Later, she celebrated "the fact that audiences are really open to a trend that for so long was dominated by the traditional older man, younger woman narrative. I think it's exciting that people are breaking out of their boxes in different ways," she told The Hollywood Reporter. In July 2026, she admitted that her experiences inspired her to take on the role. "Experiencing the double-standard first-hand has been fascinating from an anthropological standpoint," she said on "The Run-Through with Vogue" podcast in July 2026.