All the Lovely Ladies Prince Harry Has Dated

Natalie Pinkham
As Harry started frequenting London's bars and clubs in 2003, TV presenter Natalie was often by his side, and although they never dated, there was always a question mark over the exact nature of their tactile and flirty relationship.

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Image Source: Getty / Eamonn M. McCormack

Lauren Pope
The glamour model had a make-out session with Harry in a club in 2004, and they exchanged numbers. However when he texted to meet up again she blew him out, later telling Digital Spy, "He asked if I wanted to meet him with a group of friends at a bar. He was going soon and I didn't think I had time to get ready and I didn't want to meet Prince Harry looking like crap. I panicked and decided not to take him up on his offer."

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Chelsy Davy

Image Source: Getty / Shaun Botterill

Chelsy Davy
The pair met when they attended neighboring schools, and fell head-over-heels in love, but as Zimbabwean Chelsy later studied in law in South Africa and Harry was based in the UK, they were in an on and off relationship for from 2004 to 2011. During that time Chelsy met the Queen, and was by Harry's side for important ceremonial military events and the Diana Memorial Concert, but the couple split for good just after attending William and Kate's wedding together.

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Image Source: Getty / Paul Morigi

Catherine Ommanney
Before Harry and Chelsy were in an established relationship, the interior designer and divorced mother of two — who later joined The Real Housewives of D.C. — went public about her Harry make-out session in 2007. When she was 34 and he was 21 the pair ended up kissing at a friends' house on a night out, and exchanged texts for a few days afterwards.

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Image Source: Getty / Dave M. Benett

Natalie Imbruglia
When Harry and Chelsy were on a break in 2009, the prince and the Australian actress and singer met through mutual friends and they dated for a few months. During their brief relationship, Harry attended Natalie's birthday party, and they were also spotted bowling and attending a Killers concert together.

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Image Source: Getty / Dave M. Benett

Caroline Flack
In the same year, Harry also had a brief relationship with the TV presenter, after being introduced by their mutual friend Natalie Pinkham. However Caroline wrote in her autobiography Storm In a C Cup, "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." Before the end of the year, Harry was celebrating his 25th birthday with Chelsy in Botswana.

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Image Source: Getty / Gary Gershoff

Camilla Romestrand
Harry dated the Norwegian lead singer of rock group Eddie the Gun for a couple of months towards the end of 2010, but before long the prince was reuniting with Chelsy once again.

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Image Source: Getty / Nick Harvey

Florence Brudenell-Bruce
When Harry and Chelsy split for good in 2011, he and the aristocratic lingerie model enjoyed a summer romance. The pair had known each other for years but went their separate ways as Harry headed to the US for helicopter training.

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Image Source: Getty / Mike Marsland

Mollie King
Posh, pretty and blonde — Saturdays pop singer Mollie was certainly the prince's type, and the pair were spotted dancing together at Harry's favorite bar Bunga Bunga. However, in a situation reminiscent of Harry's dalliance with Caroline Flack, after their night out was made public, Harry cooled their fledgling romance. Mollie later confirmed to Closer magazine, "We did go out for a drink."

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Image Source: Getty / GLYN KIRK

Cressida Bonas
After meeting through Harry's cousin Princess Beatrice, Harry and Cressida had a two year relationship from 2012 to 2014. They were first spotted together in the summer having post Dark Knight Rises premiere drinks at Le Salon. They went on to vacation together, attended her sister's wedding, and in a sure sign it was getting serious, 'Cressie' accompanied Harry on one of his charity engagements, however, they split a few months later.

Camilla Thurlow
After they first hooked up on a night out in London in 2014, Harry invited Camilla to go on vacation with him. As the prince headed off on a yacht around St Tropez with friends, the former Miss Edinburgh — who now works for landmine charity The Halo Trust — was by his side. However when Harry celebrated his 30th birthday a few weeks later, Camilla was nowhere to be seen.

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Image Source: Getty / Chris Jackson

Ellie Goulding
Ellie has long had royal connections — she sang "Your Song" for William and Kate's first dance at their wedding, and has performed at numerous royal events over the years. But it wasn't until this year that she was linked to the prince, when they were spotted making out at a polo match.

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Image Source: Getty / Andrew Toth

Meghan Markle
The prince and the pop star was small fry compared to the Harry/Meghan juggernaut currently taking over headlines. They were introduced by — who else?! — mutual friends when Harry was in Toronto in May to promote the 2017 Invictus Games, and have been in touch ever since. Meghan was in the UK over the summer, but where will their next liaison be? Or will the publicity surrounding their budding relationship sound the death bell for Harry, as it has before?

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