When you think of Prince Harry’s ex-girlfriends, Chelsea Davy or even possibly Cressida Bonas are the first to come to mind. However, in 2009, he was pictured with Love Island show host Caroline Flack. So what happened between the two of them?

As those following Harry’s lawsuit against Mirror Group Newspapers over hacking allegations will know, photos of the ‘Spare’ author with Flack were put on public display in 2009. According to The Guardian newspaper, the prince told the court that after weeks of correspondence, Harry and Flack planned to meet at the group. But photographers were already on hand by the time they arrived at the venue – the home of his friend Mark Dyer. And Harry claims the photographers went to great lengths to conceal themselves. “They were hiding under the car,” he said.

The date soon became headline news – and the damage to a possible courtship was done. The prince and the presenter subsequently broke up, and Harry only spoke about it recently as part of the legal proceedings. As for Flack, she also kept details of the situation private until her heartbreaking death in 2020. So, what did they both say? 

This story has had an impact on Caroline’s public persona

It is worth noting that despite the photos together, Caroline Flack openly stated that she and Prince Harry did not have a relationship. Most of all, in an interview with the This Morning program, she laughed at the idea that they might have moved on if they hadn’t been photographed on that fateful night. 

Still, there is no denying that the media attention she and her family received for the story significantly impacted Flack. In the book, she writes that her entire public persona was turned upside down when the press accused her of social climbing. 

Eventually, after learning that the press was targeting all her Facebook friends, Flack hid at her sister Jodie’s house and stopped working for a while. 

And Prince Harry claimed he had trust issues.

Caroline Flack wasn’t the only one to backtrack after the publication of photos of her with Britain’s Prince Harry. Following the TV presenter’s example, the Duke of Sussex became increasingly withdrawn and distrustful of Flack and Mark Dyer.

“Given that only the three of us knew about the plan, I was extremely suspicious and convinced that someone had leaked information to the press,” he told London’s High Court (according to The Guardian). However, he has since changed his stance. 

Although Flack has long since died, in an interview with Jeremy Vine, her mother, Christine, revealed that her daughter was also often suspicious of friends’ and relatives’ interactions with the press (via Evening Standard). Christine has made it clear that she supports Prince Harry to the end. “I think Harry is doing it for everyone … and I think he’s a courageous man because there’s so much trouble coming down on him as well,” she noted. Harry and Flack may have never been in a relationship, but they’ve been through a lot together.