Prince Harry former girlfriends: From TV Presenters to Models and Singers, all who fell for the Ginger Prince before Meghan Markle

Time of India

03-05-2025

Prince Harry
might have found her 'forever' in Meghan Markle and is a happily-married man with two kids now, but the Ginger Prince of the British Royal Family has had quite a run when it comes to the romance roulette.
We won't go into disagreements with Meghan as she went on record and called her husband 'a fox', implying how handsome he is. In fact, we have a string of past relationships to add up in favour of Meghan's argument!
Before Prince Harry married Meghan Markle in 2018, after a two-year romance, he enjoyed the on-again, off-again company of Chelsy Davy for many years and had a serious relationship with Cressida Bonas.
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Although Harry certainly enjoyed his single years, when he was ready to settle down, he knew Markle was the one 'the very first time [they] met,' according to Harry at their engagement photo call, via Harper's Bazaar.
But do you know who these women were who fell hard for the Ginger Prince?
Take a look!
Natalie Pinkham (2003)
Natalie Pinkham and Prince Harry first met in 1999 at the Rugby World Cup, according to US Weekly. A few years later, they began dating in 2003. They crossed paths several times since then due to her work and his charity efforts, and they reportedly remain friends today.
Cassie Sumner (2003)
The palace was relieved that this one-night stand didn't turn into more!
A 19-year-old Harry met model Cassie Sumner at a nightclub during his wild youth. They reportedly spent an evening together, which Sumner talked about in an interview. She joined him at his private table, and the fun began. She said, 'He seemed fascinated with my breasts because he spent more time looking at them than my face.' Sumner added that at one point, Harry cuddled up to her, ran his hands up and down her thighs, and whispered that she looked sexy. When he asked if they could go somewhere private, she told him, 'Don't be silly,' but it only seemed to encourage him more. It's not surprising that this fling ended quickly, letting the royal family take a breath of relief.
Chelsy Davy (2004-2011)
Harry had a sweet but complicated on-again-off-again relationship with Chelsy Davy. They broke up and got back together several times, and the royal family welcomed her back each time. Chelsy even attended Prince William and Kate Middleton's wedding in 2011. However, she felt that the royal life was not for her because of the media attention. She said, 'It was so full-on: crazy and scary and uncomfortable,' and she found it hard to cope when things were bad.
Astrid Harbord (2009)
Harry's short romance with Astrid Harbord, a friend of Kate Middleton, happened while he was taking a break from Chelsy Davy. They were seen partying together in London. After their fling, they stayed friends, and Astrid even became Harry's PR representative. Their professional relationship ended when Harry became serious with Meghan, and they changed their household communication style.
Caroline Flack (2009)
TV presenter Caroline Flack was excited to meet Prince Harry through a mutual friend. They spent some time together in 2009, but when the press started to notice, they decided to end it. In her memoir, 'Storm in a C Cup', she wrote, 'I was no longer Caroline Flack, TV presenter; I was Caroline Flack, Prince Harry's bit of rough.'
Mollie King (2010)
Mollie King, a singer from The Saturdays, denied dating Prince Harry. She told the Evening Standard, 'No, I'm not going out with him – I'm serious. Everyone wants to believe it because he's royalty. Everyone would like it to be true but it's not. He's very out of my league, come on.' But two years later, she admitted to Closer magazine, via Digital Spy, that they did go out for a drink.
Camilla Romestrand (2010)
Prince Harry was linked with singer Camilla Romestrand, and it seemed like they might have had a casual relationship. A source told News of the World, via CBS News, that she talked about their friendship and staying overnight at 'the Palace.' She described him as a 'total gentleman' but didn't share more details. Camilla focused on her music career after they broke up.
Florence Brudenell-Bruce (2011)
After Harry ended his relationship with Chelsy Davy, he had a brief fling with model Florence Brudenell-Bruce. This romance didn't last long because of trust issues. An insider told the Daily Mail that Florence felt Harry had a wandering eye and didn't like being unsure about who he was with when they were apart.
Cressida Bonas (2012-2014)
Cressida Bonas was Harry's last serious girlfriend before Meghan. They genuinely cared for each other, but they split due to pressure from media attention. Royal author Katie Nicholl revealed that Cressida felt overwhelmed watching coverage of William, Kate, and George during their tour of New Zealand and Australia. She told Harry she didn't want that kind of attention. Harry felt heartbroken over this.
In his memoir 'Spare', Harry shared that Cressida was important to him. He noted that he cried for the first time about his mother while talking to her. Despite this bond, they broke up because she didn't want the stress of being part of the royal family.
Ellie Goulding (2015)
People wondered if Prince Harry dated pop star Ellie Goulding in 2015. The Daily Mail reported they were seen chatting, flirting, and kissing at a post-polo event, but no pictures were taken, so it remains unconfirmed. Their friendship began when she performed at his 30th birthday, and she participated in the closing ceremonies at the 2014 Invictus Games, a charity Harry cares about.
Even if they had a romantic moment, Harry met Meghan the following year, and the rest is history. Staring their secret romance in 2016, the pair married in 2018, and now are parents to two kids – Archie and Lilibet.
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