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If you’ve been keeping an eye on the headlines lately, you know things are moving fast for Olivia Wilde. Honestly, she’s spent the last few years trying to keep a lower profile after the absolute circus that was her relationship with Harry Styles. But you can't stay a mystery forever in Hollywood.
Right now, Olivia Wilde is dating Caspar Jopling, a 33-year-old British art dealer.
This isn't just some random rumor, either. They’ve been spotted everywhere from the quiet streets of London's Primrose Hill to the high-energy parties of New York Fashion Week. It’s a bit of a shift for her. After the "Don't Worry Darling" drama and the very public custody battles with Jason Sudeikis, she seems to be leaning into a life that's a little more... sophisticated? Art-world chic?
Whatever you want to call it, the "who is dating Olivia Wilde" question finally has a solid answer as we head into 2026.
The Caspar Jopling era: How it started
The timeline is pretty interesting. Most people didn't see this coming, but the pair reportedly started seeing each other around July 2025.
If the name Caspar Jopling sounds familiar, it’s probably because he was famously married to pop star Ellie Goulding. They split back in 2024, and for a while, everyone was wondering who he’d end up with. Turns out, it's Olivia.
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Things really heated up in September 2025. They were caught by the paparazzi in London having a three-hour dinner at The Pelican, and let's just say they weren't trying to hide the PDA. Witnesses described them as looking like "teenagers in love." A few days later, they made their first "official" public appearance (well, sort of) at a W Magazine party during New York Fashion Week.
Why this relationship feels different
You’ve probably noticed that Olivia isn't doing the whole "paparazzi walk" thing as much as she used to. After the Harry Styles era, she apparently told friends she was done with the "public spectacle" side of dating.
Caspar is a bit of a different breed than her exes:
- He’s an Eton-educated art dealer.
- He works with blue-chip art at Sotheby’s.
- He’s 41, and she’s 33? No, wait—she’s actually 41 and he’s 33. It’s an eight-year age gap, but it seems to work for them.
- He has a son, Arthur, with Ellie Goulding, so he understands the "co-parenting" life that Olivia is constantly navigating.
What happened to the other guys?
Before Caspar became the main man, 2025 was a bit of a whirlwind for Olivia's dating life. For a second there, everyone thought she was with Dane DiLiegro.
Remember him? The 6’8” former basketball player who played the Predator in Prey? They were spotted looking very cozy at a Lakers game in January 2025. Sources at the time said she was "smitten" and that he was a "breath of fresh air." It seemed like a solid match—he’s a chef, an actor, and basically a giant. But like many Hollywood "situationships," it seemed to fizzle out by the summer.
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There was also some chatter about her and producer Saul Germaine. They were seen together in London while filming The Invite, but Olivia actually went into the Instagram comments herself to laugh those rumors off. It’s rare for her to engage like that, but she clearly wanted to set the record straight: they’re just work friends.
The "London Move" and the real estate clues
Here is where it gets juicy. In January 2026, news broke that Olivia Wilde sold her Los Angeles home in Studio City.
She didn't just sell it; she took a hit. She sold it for $5.23 million, which was about a $700,000 loss from what she paid in 2023. People don't usually sell at a loss unless they are in a massive hurry to leave.
The word on the street is that she’s eyeing a permanent move to London. Since Caspar is British and based over there, it makes total sense. Plus, she’s always had a soft spot for the UK. If she moves, it would mean a major shift in her custody arrangement with Sudeikis, but insiders say they are finally in a "good place" and presenting a united front for their kids, Otis and Daisy.
A quick refresher on the Olivia Wilde dating timeline
If you’re trying to keep track of how we got here, it’s been a long road:
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- Tao Ruspoli (2003–2011): She married this Italian prince when she was just 19 on a school bus. Very indie.
- Jason Sudeikis (2011–2020): The long-term engagement that gave us two kids and eventually led to that viral moment where she was served custody papers on stage at CinemaCon.
- Harry Styles (2021–2022): The relationship that broke the internet and started a million conspiracy theories about spit-gate and Florence Pugh.
- Dane DiLiegro (Early 2025): The rebound that felt like a movie script.
- Caspar Jopling (July 2025–Present): The current, more private chapter.
What’s next for Olivia?
It looks like 2026 is going to be a year of big transitions. Between the house sale and the public appearances with Caspar, she seems to be prioritizing her personal happiness over the Hollywood "it-girl" grind.
She’s still directing—The Invite is one of the most anticipated projects on her slate—but her focus seems to have shifted toward a more European lifestyle.
If you're following her journey, keep an eye on the London real estate market. That’s usually the biggest tell when a celebrity relationship is getting serious. She’s looking for a fresh start, and it seems like she’s found it with a 6'3" art dealer who stays away from the pop-star spotlight.
Key Takeaway for Fans:
If you see Olivia Wilde in the news right now, it's likely about her move to London or a gallery opening with Caspar. She’s finally moved past the "Don't Worry Darling" era and seems to be thriving in a much quieter, more mature relationship.
Actionable Insights for Celebrity News Followers
- Follow the Real Estate: When celebrities sell homes at a loss, it’s a huge indicator of a lifestyle change. Check property records in the UK if you want to see where she’s heading next.
- Ignore the "Work Rumors": Olivia is a director and producer. She’s going to be seen with men like Saul Germaine often; don't assume every lunch is a date.
- Check the Art World: Since Caspar is a major player in the art scene, you’re more likely to see Olivia at a Sotheby’s event than a Hollywood nightclub these days.