A Look Back At Prince Harry’s Dating History Before Meghan Markle

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Prince Harry may be head over heels about Meghan Markle, the star of Suits, but the British royal has been linked to plenty of other women in the past. Take a look at the Prince’s history of romances, from the flings that were never verified to the on-and-off affairs.

Natalie Pinkham

The young royal was said to have dated TV presenter Natalie Pinkham in 2003. Although none of them has ever openly acknowledged a love connection, they are said to have stayed friends even after being associated. Pinkham, a Sky Sports F1 correspondent, is now married with two children.

Cassie Sumner

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Sumner revealed a controversial account of her encounter with Prince Harry in London’s Chinawhite nightclub in 2004. (Harry was 19 and she was 21). But it seems the affair only lasted for that one evening.

Chelsy Davy

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Harry’s romance with Chelsy Davy, which lasted intermittently from 2004 to 2011, is still his longest union to date. Initially meeting while Prince Harry was on a gap year in Cape Town, the two dated intermittently for years. Following a 2009 breakup, Davy and Harry resumed their romance, and the two even went on a date to the Duke and Duchess of Cambridge’s wedding in 2011. Despite ending their relationship permanently, Davy said they will “always remain friends.”

Astrid Harbord

Credit: Davidson/O’Neill/REX/Shutterstock

Astrid Harbord, a friend of Kate Middleton, and Harry were spotted out together in London in 2009, leading to a brief association between the two.

Caroline Flack

Credit: Mike Marsland/WireImage.com

In June 2009, Harry was also linked to Caroline Flack, the host of the X Factor. Flack said in her account that a common acquaintance set up the two to start dating. But they broke up as soon as the connection became known. “That was it as soon as the news spread. We had to cut off our contact. I was Caroline Flack, Prince Harry’s bit of rough, not Caroline Flack, TV presenter “Flack said.

Camila Romestrand

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Following his split with Chelsea Davy in 2010, Harry dated Norwegian singer Camila Romestrand for a brief period of time. As per CBS, Romestrand told her friends that she remained the night at Clarence House, where Prince Harry even gave her breakfast in bed. Prince Harry, however, never corroborated Romestrand’s story.

Florence Brudenell

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The British newspaper The Sun said that Harry dated the model/actress Florence Brudenell in 2011. They reportedly had “secret trysts” when visiting her Notting Hill residence in London and kept their relationship under wraps. A representative for the Palace said, “We don’t comment on the Prince’s personal life,” when questioned about Prince Harry’s new partner.

Cressida Bonas

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After purportedly being introduced by Princess Eugenie, actress Cressida Bonas dated Prince Harry from 2012 until 2014. According to reports, Bonas’ inability to handle Harry’s close public attention caused the relationship to end. She later talked openly about the encounter in a BBC Radio interview.

Mollie King


The English singer and member of The Saturdays admits to dating Prince Harry for a brief period of time back in 2012. They were seen together at a London bar, but according to rumors, Harry broke things off with the singer because she was too outspoken about their relationship in public.

Ellie Goulding

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Despite never having a romantic relationship, Prince Harry and pop artist Ellie Goulding ignited suspicions in the spring of 2016 after cuddling up at a polo in Bershire. The two were subsequently seen kissing after spending a lot of time “sitting together beneath blankets,” according to sources (even though there is no photograph of this). After Goulding performed at Prince William and Kate Middleton’s wedding in 2011 and then again at Prince Harry’s Invictus Games in 2014, the two are said to have known one other for a long time.

Meghan Markle

(Photo by Karwai Tang/WireImage)

In 2016, Prince Harry and Meghan Markle started dating covertly, but things took a serious turn. The monarch issued a rare public statement encouraging people to stop bothering Markle and her family months after they started dating. The two kept their relationship very private, although they did go on a weeks-long safari together in Africa and Markle attended with Harry to Pippa Middleton’s wedding. The pair made their royal engagement announcement after finally seeing the Queen. Archie Harrison and Lilibet Diana, their two children, were born on May 19, 2018, the day after their wedding. They now reside in California with their kids after resigning from their position as senior royals.

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