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Olivia Wilde Caught Kissing A New Mystery Man In A Chic Trench Coat During A Recent Dinner Date Amid Ex Harry Styles’ Reported Fling With Zoë Kravitz: ‘She Likes Them Young’

September 9, 2025 by Abigail Connolly

 
Splash News

Olivia Wilde is one of Hollywood’s most talked-about bachelorettes, ever since her marriage to actor Jason Sudeikis ended and she had her infamous age-gap relationship with Harry Styles. Now, after a few months of living the single life, it looks like she may be off the market once again.

The actress and director was recently spotted wearing a long, stylish trench coat while smooching Caspar Jopling, the ex-husband of pop singer Ellie Goulding. She had on a classic fall date night look as they shared a kiss after what looked like a dinner date between the two of them. Their night out doesn’t come long after sources claimed Olivia is not looking for anything “serious” right now, but is “having fun” dating around. Read more about her date night look and rumored fling below.

Olivia Wilde Is Photographed Kissing Ellie Goulding's Ex-Husband In A Chic Fall Trench Coat

It's no secret that the glamorous actress has been through a lot in her personal life over the last few years, as not only did she breakup and enter a custody battle with the father of her children and fiancé of seven years, Jason Sudeikis in 2020, but she also had a scandalous brief relationship with megastar and co-star Harry Styles, who is 10 years younger than her.

Once she and the British pop star broke up, she took a step out of the spotlight, quietly working on other projects and every once in a while being seen on a more casual date. Until now, that is. This week, she was caught sharing a kiss with Caspar Jopling, an English art dealer and the ex-husband of British popstar Ellie Goulding, in London. The pair were reportedly on a dinner date together, as they were seen embracing and kissing outside a London restaurant. You can see the photos of them here!

Olivia had on a classic fall date night look, sporting a large, beige trench coat that went all the way down to her ankles. In the sneaky paparazzi photos, she seemingly had the coat on over a pair of trousers or jeans, and was seen wearing a casual, simple white t-shirt at dinner. She paired the look with a cross-body purse and left her highlighted blonde hair down.

The Internet Reacts To Olivia's Dinner Date & New Paparazzi Photos On Social Media

Once the Don't Worry Darling director was papped on her dinner date, as per usual, the pictures were spread across social media, where the internet began reacting to the photographs, many of them wondering if her rebound with Caspar has anything to do with her ex, Harry, seemingly moving on recently.

The "Watermelon Sugar" singer has been photographed holding hands with actress Zoë Kravitz in New York City and Rome over the last few weeks, showing lots of PDA, and even being seen having lunch with her rockstar dad, Lenny Kravitz. Therefore, fans of Olivia's were happy to see her out and about and are hoping this potential new relationship sticks and lasts.

"Good for her," commented a fan under Instagram photos of Olivia and Jaspar. "They look so cute," added another.

"I hope she found the right partner for her this time," commented an Instagram user.

One Instagram user joked about Caspar being eight years younger than Olivia, referencing her and Harry's former age gap as well, and wrote, "She likes them young."

While a source close to the House actress recently stated that she's "having fun" and dating around, not looking for anything too "serious," we'll be curious to see if this fling with Caspar turns into something more.

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