The youngest of two boys born to King Charles III and the late Diana Spencer, Princess of Wales, Prince Harry’s life has been long characterised by periods of tumult and controversy, alongside a string of relationships with celebrity girlfriends.
Where that is concerned, Harry has been especially vocal about the struggles that he has faced in his love life leading up to his eventual marriage to Meghan Markle, the Duchess of Sussex. In fact, he has claimed during his most recent litigation against the Mirror Group of newspapers that media intrusion led to the breakdown of his relationship with former flame Chelsy Davy.
In light of that, here is a concise retrospective of the relationships that have come to define Prince Harry’s dating life under the public eye, both confirmed and alleged.
A list of Prince Harry’s girlfriends that defined his love life
1. Natalie Pinkham (2003)
The earliest known name to be linked with Prince Harry romantically was British television presenter Natalie Pinkham. The pair were said to have first met during the 1999 Rugby World Cup, before dating briefly in 2003. The relationship may not have necessarily gone far, with Natalie now being married to television executive Owain Walbyoff with two children, but both she and the Prince continue to remain good friends.
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2. Cassie Sumner (2004)
Actress Cassie Sumner, who most notably dated comedian Russel Brand previously, revealed in a 2004 interview how she had shared a rather scandalous fling with Prince Harry at London‘s Chinawhite nightclub. At the time, she was 21 while he was 19. Cassie’s account of the evening claims that the Prince had ‘cuddled up’ to her after making eye contact and inviting her to join his private table. Prince Harry never confirmed her claims.
Cassie was also said to have briefly dated Commander James Hewitt, the man whom which Harry’s mother, Diana, was previously having an affair with. She is now married to Portugal national team midfielder Jose Fonte.
3. Chelsy Davy (2004 – 2011)
Zimbabwean lawyer and businesswoman, Chelsy Yvonne Cutmore-Scott, otherwise known as Chelsy Davy, was Prince Harry’s first, long-term girlfriend. The pair shared a committed, albeit on-again-off-again, romance from 2004 to 2011, first meeting when Harry spent a gap year in Cape Town. Things eventually became serious between the pair, with Chelsy being invited to meet the late Queen Elizabeth II. In his book Spare, Harry recounts how she was ‘different’, in that she did not appear concerned by property, rank, or royalty.
However, the relationship eventually fell apart, with Chelsy telling the Times that “It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn’t cope,”. She is now married and has one child.
4. Caroline Flack (2009)
Former X-Factor TV presenter Caroline Flack was briefly known to have dated Prince Harry after being introduced by their mutual friend and Harry’s ex, Natalie Pinkham. Affectionately referring to the Royal by the nickname of ‘Jam’, as he had ‘jam coloured-hair and was really sweet’, Caroline said that the romance ended for the same reason that many of Harry’s relationships did: the media.
In her autobiography, Storm in A C Cup, she said “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.”, after their relationship was made public knowledge.
5. Camilla Romestrand (2010)
Norweigan singer Camilla Romestrand claimed that she had Prince Harry had once briefly dated after he had broken up with Chelsy Davy in 2010. Her account to friends alleges that she was invited to stay over at Clarence House, and was even served breakfast in bed by the Prince himself, reports CBS. But this was never confirmed by Prince Harry.
6. Mollie King (2010)
Another alleged fling was said to have occurred between English singer-songwriter Mollie King of The Saturdays and Prince Harry. She claims that they first met in 2010 at the Asprey World Class Cup at Surrey’s Hurtwood Polo Club, and they went out ‘for a drink’. Apparently, Harry was the one who broke off the relationship after finding Mollie to be ‘too open’ where details of their romance were concerned.
7. Florence Brudenell (2011)
Upon his 2011 breakup with Chelsy, Prince Harry was reportedly involved with actress and model Florence Brudenell. Tabloid coverage of the pair indicated that they would often meet at Brundenell’s home in Notting Hill for ‘secret trysts’. But it was alleged that she ended the relationship, with one source telling the Daily Mail that Brundenell felt that Harry had a ‘wandering eye’.
8. Cressida Bonas (2012 – 2014)
Across the span of two years from 2012, Prince Harry dated Cressida Bonas after being first introduced to her by his cousins, Princess Eugenie and Princess Beatrice. She is oft considered to be Prince Harry’s second, long-term girlfriend.
Once again, their relationship would eventually falter under the weight of media scrutiny, with Cressida speaking at length about her experience from the time during an interview with BBC Radio. She has since married Harry Wentworth-Stanley.
9. Ellie Goulding (2015)
Perhaps the most internationally recognised name on this list, bonafide pop star Ellie Goulding sparked rumours of a potential romance with Prince Harry when they were both spotted sharing an intimate moment together under a blanket during a polo match.
But of course, no official statements or reports of the pair ever dating exist. Both Goulding and the Prince remained good acquaintances for a considerable period of time, with the former even performing at Prince William and Princess Catherine’s wedding in 2011.
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10. Meghan Markle (2016)
The Duchess of Sussex, Meghan Markle, first met Prince Harry in the summer of 2016 after being introduced through a mutual friend. At the time, Meghan was an actress on the TV series Suits and had been divorced from American film producer Trevor Engelson in 2014.
Initially, the pair kept their relationship discreet and much was left to speculation. But it eventually became serious, leading to a statement being made from Harry’s office to urge members of the public to stop harassing Meghan’s family. After going on a week-long trip to Africa together and accompanying Harry to Pippa Middleton’s wedding, Meghan was invited to meet the Queen. The couple wedded in 2018 and now have two children together.
Feature and hero image credits: Photo by Max Mumby/Indigo/Getty Images, Photo by Karwai Tang/WireImage
This story first appeared on Lifestyle Asia Kuala Lumpur