Prince Harry’s Exes Kiss And Tell All About Him

These days, it’s difficult to picture Prince Harry with anyone other than Meghan Markle. She’s not just the mother of two of his children. She’s also the main reason that he stepped back from royal duties and eventually moved to America.

However, before Meghan came along, Harry dated quite a few lucky ladies. At the time they were dating, most of these gals practiced the British “stiff upper lip” and said nothing about the relationship. Over time, though, more than a few of them were willing to “kiss and tell” about the prince!

So, what do all these exes really think about Prince Harry? Trust us: you’re going to be shocked!

Cassie Sumner

While Prince Harry is prim and proper these days, he was wild and a bit unhinged when he was younger. In between partying at clubs and constantly landing in the tabloids in the early 2000s, he met actor and model Cassie Sumner.

In 2004, the two of them met at London’s China White bar. The two didn’t exactly have a major relationship. According to the Mirror, Sumner said that Harry was drunk and invited her to hang out at his table. They were only together for about 45 minutes before the club closed and they went their separate ways.

Does Sumner think of Harry as the one that got away? Hardly: “If I’m honest, I didn’t really fancy Harry,” she said. “I prefer more muscles on a man. … Anyway, I can’t see myself getting invited home for tea with Prince Charles and Camilla!”

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Chelsy Davy

2004 was a busy year for Prince Harry. It was that same year he met heiress Chelsy Davy. And before Meghan Markle came along, this was the woman Harry seemed likeliest to marry.

The two had an off-and-on romance that lasted between 2004 and 2011. They had enough chemistry that sparks visibly flew when they were together, but it just wasn’t enough for either of them to make a long-term commitment.

So, what did Davy think of Harry after the fact? In 2016, she told The Times that they mostly broke up because she didn’t want the media attention that came from dating a prince. “Crazy, and scary, and uncomfortable. I found it very difficult when it was bad. I couldn’t cope. I was young, I was trying to be a normal kid and it was horrible.”

Caroline Flack

Some of Harry’s exes were already famous in their own right before they dated. For example, Caroline Flack was a previous contestant on Strictly Come Dancing and a host of X Factor in 2009 when she began dating Harry. They only dated briefly before breaking things off.

However, Flack later penned an autobiography titled Storm in a C Cup. According to the Sun, she wrote that “To meet a prince is so unlikely it would be weird not to acknowledge it. 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.”

In other words, it seemed Flack didn’t like the attention that came from dating Harry. Tragically, she committed suicide in 2020, and many wonder if the negative media attention from her time with Harry was a contributing factor.

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Cressida Bonas

Cressida Bonas was born into an interesting heritage. After all, she is the daughter of famous socialite Lady Mary Gaye Curzon, and she’s even connected to King Edward VII. Despite that, she is wary of media attention, and that ultimately spelled doom for her relationship with Harry.

The two began dating in 2012 after being introduced by Princess Eugenie, a cousin of Harry. The couple dated for two years and tried to keep things quiet, but this didn’t keep the rumor mill from churning out constant headlines, including breathless headlines about the two getting married.

In 2020, Bonas disclosed to ES magazine that she is still dealing with the media fallout from her romance with Harry. “No one likes to be labeled, no matter what it is about or where they come from. The hurdles and barriers for me are when I’m trying to do my work and people want to talk about him. I work very hard and love what I do — I just want to continue. But it is still something I have to contend with.”

Mollie King

Mollie King was one of Harry’s more famous ex-girlfriends. That is because she was a member of the female musical group The Saturdays, and she met Harry in 2010 at the height of her fame. In 2012, the two began dating and tried to play it cool, denying that any relationship existed. Still, numerous photos of the two partying together put that denial to rest.

The relationship didn’t last long, and King didn’t have a lot to say about Harry afterward. But as the Daily Beast reports, she did admit that the relationship didn’t have much of a chance and wasn’t much of a relationship at all. “He’s very out of my league, come on. I just went out with loads of friends and all of a sudden we are an item. But we’re not.”

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Camilla Romestrand

Does Harry have a thing for female musicians? Considering his brief romance with Norwegian frontwoman of Eddie the Gun, Camilla Romestrand, that may just be the case!

The two met in 2010 when Harry wasn’t actively dating Chelsy Davy. Harry and Romestrand had a mutual friend, and that friend invited Romestrand back to Harry’s home. Later that year, Cosmopolitan UK reports that the two were seen partying at the Chelsea nightclub Raffles (a personal favorite hangout spot of Harry’s). 

Romestrand herself never actually said anything about her time dating Harry, but one of her friends spilled the beans. As reported by CBS News, Romestrand told her buddy how Harry was a “total gentleman” who would bring her breakfast in bed!

That same friend said Romestrand ultimately wanted to call things off because she worried life with Harry was starting to overshadow her career as a musician.

Florence St. George

Historically, royalty kept romance “in the family.” And that happened when Harry dated Florence St. George, who is actually Harry’s eighth cousin.

The two began a summer romance in 2011 that only lasted a couple of months. The alleged cause of their breakup is rather shocking. According to the Daily Mail, things fell apart because Harry couldn’t stop scoping out other women. One source close to the matter told the publication, “She felt he had a wandering eye all the time and she wasn’t really into not knowing who he was flirting with or talking to when they were apart.”

How does St. George feel about their relationship now that it’s over? In her own words, she told The Telegraph, “My privacy ended abruptly, and the scrutiny began. A new story would appear almost every day in the press, my school friends were interrogated, and there were photographers outside my front door. I take my hat off to those people who can cope with that lifestyle, but I knew I couldn’t. Although it was sad at the time, I feel lucky that the relationship was short-lived.”

Given what all these women have had to say, it seems Harry was lucky to find Meghan Markle when he did!

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