Olivia Wilde's Dating History: From Jason Sudeikis to New Beau Caspar Jopling

As a highly sought-after A-list actress, Olivia Wilde can have her pick of Hollywood's most notable men - and all of her romances make headlines.

Prior to her rise to fame, Wilde was married to Italian-American filmmaker Tao Ruspoli when she was just 19 years old. Following their 2011 split, the actress was romantically linked to several big names in Hollywood, including Ryan Gosling.

However, it was her relationship with Jason Sudeikis, with whom she shares two children, that captivated fans for nearly a decade.

Since they parted ways in 2020, calling off their engagement, Wilde has been spotted with the likes of Harry Styles and art dealer Caspar Jopling.

Scroll down to explore Wilde's dating history through the years:

Tao Ruspoli

The Tron: Legacy actress was married to the son of Prince Alessandro Ruspoli, Tao Ruspoli, from 2003 to 2011. Wilde filed for divorce in March 2011 citing "irreconcilable differences" and their case was finalized that September.

"I really had a sense that I had stunted my growth. I think that's one of the things that made me feel so uncomfortable in my marriage," Wilde said on Lifetime's The Conversation in 2012 of getting married so young. "It was really no fault of my husband. It was me realizing that I had sort of arrested development. I knew the only way I was going to grow the f*** up was to learn to take care of myself."

Ryan Gosling

Three weeks after announcing her split from Tao Ruspoli in February 2011, Wilde sparked dating rumors with Crazy, Stupid, Love actor Ryan Gosling when they were spotted holding hands at an aquarium in Kentucky in March 2011. Before that, they were seen enjoying a casual brunch together at Nada restaurant in Cincinnati, Ohio, and getting cozy at the Golden Globes in January 2011.

Justin Timberlake

Wilde was linked to Justin Timberlake in April 2011 while he was on a break from now-wife Jessica Biel. After they were spotted dancing and flirting in L.A., a source told Us that the In Time costars "were obviously a couple or on a date." She later slammed the dating speculation, tweeting, "Cool it, honeybadgers. We are just friends and have been for years."

Bradley Cooper

After Bradley Cooper ended his two-year relationship with Renée Zellweger in 2011, Us revealed that June that The Words costars were "definitely hooking up" after getting to know each other on set.

Jason Sudeikis

Wilde met Jason Sudeikis in May 2011 at a Saturday Night Live wrap party following the season 36 finale. They began dating that November and got engaged in 2013. Us confirmed in November 2020 that the Drinking Buddies costars - who share son Otis (born in 2014) and daughter Daisy (born in 2016) - split after nine years together.

"They've been separated for months now and there really is no drama. They're handling this like adults. It's all about coparenting their kids, Daisy and Otis. That's the priority for them," a source exclusively told Us at the time.

Harry Styles

The filmmaker was linked to "Watermelon Sugar" crooner Harry Styles in January 2021 when they were photographed attending his pal's wedding together. A source told Us that the pair "had chemistry almost instantaneously" while working on the set of their film, Don't Worry Darling, in which she also directed.

In November 2022, Us confirmed that the pair split after less than two years of dating.

Dane DiLiegro

Athlete-turned-actor Dane DiLiegro sparked romance speculation with Wilde in January 2025 after they were spotted at the Los Angeles Lakers game against the Boston Celtics. The pair were seen looking cozy sitting side-by-side while watching the game. DiLiegro and Wilde, however, never publicly addressed their connection.

Caspar Jopling

Wilde was first linked to Ellie Goulding's ex-husband, Caspar Jopling, in September 2025. At the time, Wilde was photographed kissing Jopling outside a restaurant in London. The pair were spotted later that month outside W Magazine's New York Fashion Week party at Chez Margaux in the Big Apple.

Wilde teased her relationship with Jopling in January 2026 by sharing a steamy photo of the couple hugging in Park City, Utah. Wilde didn't tag the art dealer in her post from Sundance Film Festival, but Us confirmed that Jopling was the man who was holding her tight while out at a restaurant in the area.

US Weekly

This story was originally published January 29, 2026 at 5:10 PM.