In the midst of Harry’s early-2000s wild phase, the royal met model and actor Cassie Sumner at London’s China White bar. While the two spent an hour canoodling, they ultimately parted ways, and Sumner said, “If I’m honest I didn’t really fancy Harry. I prefer more muscles on a man [...] I can’t see myself getting invited home for tea with Prince Charles and Camilla!”

Later that same year, Harry met heiress Chelsy Davy and the connection between the two was immediately apparent. Despite many considering their love to be the real deal, the two ultimately split because Davy didn’t want to be in the public eye. Davy called the media frenzy, “Crazy, and scary, and uncomfortable. I found it very difficult when it was bad. I couldn’t cope.”

In 2009, Prince Harry began dating TV personality Caroline Flack, but when the media caught wind, the two decided to end their relationship. Flack said of the romance, “To meet a prince is so unlikely […] However, once the story got out, that was it. We had to stop seeing each other. I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough.”

Like Flack before her, Cressida Bonas struggled with media attention during her two-year relationship with the prince. Even years later Bonas still struggles with the media frenzy, saying in a 2020 interview, “The hurdles […] for me are when I’m trying to do my work and people want to talk about him […] it is still something I have to contend with.”

Prince Harry met singer Mollie King as early as 2010, but the two didn’t move beyond friendship until early 2012. Harry allegedly ended things because King was too candid about their relationship, but all King said about their time together was, “He’s very out of my league […] I just went out with loads of friends and all of a sudden we are an item. But we’re not.”