Who has Harry dated? From Chelsy to Cressida, a timeline of the Prince's love life

Ciara Sheppard
Contributor
Chelsy Davy, Prince Harry and Meghan Markle, and Cressida Bonas. [Photo: Getty/ Yahoo Style]

For many years, Prince Harry has been Britain’s most eligible bachelor.

But somewhere between his royal rebel teenage years and his coming-of-age as the people’s prince, Harry fell head over heels in love.

While there were a number of flings and ‘nights of passion’ that made the tabloids, there have only been three women in Harry’s life that have been publicly recognised as his significant others. 

Here, we chart them. From his first serious relationship, aged 19, with South African beauty Chelsy Davy, to his meeting with English socialite Cressida Bonas, and finally, his pairing with wife-to-be Meghan Markle.

Harry’s first love: Chelsy Davy

Prince Harry’s first love was Chelsy Davy – the Zimbabwean-born daughter of South African safari farmer Charles Davy – who he dated on-and-off for seven years from 2004 to 2011. 

Harry met Chelsy during his gap year in Cape Town in 2004, when he was 19.

Chelsy Davy lived in Cape Town but spent much of her time in London. [Photo: Getty]

Hitting it off instantly, the pair spent the entire summer together and spoke constantly on the phone when Harry returned to England that autumn, successfully managing to keep their relationship out of the public eye for months.

Harry and Chelsy kept their relationship under the radar until, while still at the very beginning of their blossoming romance, they took a romantic break to Argentina in November of that year.

When staff at the lodge they were staying at told the Mail on Sunday about their affectionate displays, the cat was out the bag and suddenly, the young couple became public property.

Prince Harry kisses Chelsy Davy during the ICC Cricket World Cup 2007 [Photo: Getty]

Royal biographer Katie Nicholl – author of Harry: Life, Loss and Love – says that Harry would take Chelsy on romantic getaways to the Shakawe Fishing Lodge in Botswana to get away from the press.

Chelsy was a regular fixture in London and also took a post-graduate degree in law at Leeds University so she could be closer to her boyfriend.

Nicholl notes that in 2005, Harry gave a rare interview about his girlfriend, but kept his feelings guarded, saying: “My girlfriend is somebody who’s very special to me… I would love to tell everyone how amazing she is. But you know, that is my private life.”

Chelsy and Harry were serious: the young blonde even met The Queen at a society wedding and was a guest at Prince Charles‘ 60th birthday.

Prince Harry and Chelsy at a rugby match in 2008. [Photo: Getty]

But the pair’s relationship was not without its dramas: photos of Harry cosying up to TV presenter Natalie Pinkham in a nightclub caused jealousy for Chelsy, and his deployment in Iraq put stress on their relationship.

In early 2009, Chelsy left a Facebook status saying: “Relationship: Not in One”

Nicholl says in her book: “The truth is Harry had a roving eye when Chelsy wasn’t around, and his flirting recently landed him in hot water.”

Getting back together in late 2009, the pair spent another year trying to work through their problems but it was proving easier said than done: Harry was back on the front line and Chelsy was back in Africa again.

“Harry’s military commitments had taken their toll on his romance with Chelsy, Kate [Middleton] was prepared to make sacrifices that Chelsy was not,” Nicholl says.

Despite their relationship seeming beyond repair, Harry asked Chelsy to be his plus one to his brother Prince William‘s wedding to Kate Middleton.

Despite the romance of the day, shortly after Chelsy and Harry were done for good.

In 2016, Chelsy gave an interview about her relationship with the Prince, telling The Times: “It was so full-on: crazy and scary and uncomfortable… I found it difficult when it was bad. I couldn’t cope. I was trying to be a normal kid and it was horrible.”

Harry’s second love: Cressida Bonas

Cressida Bonas was suspected by the media as the woman Harry would propose to.

Cressida Bonas – the daughter of 1960 covergirl Mary-Gaye Curzon and entrepreneur Jeffrey Bonas –was introduced to Harry by her good friend Princess Eugenie, Harry’s cousin, at a music festival in the summer of 2012.

Cressida Bonas was well-known on the London party scene. [Photo: Getty]

The pair spent the summer dating in secret, but before long, Harry’s infamous ‘Vegas stripping’ scandal presented them with their first road bump.

Choosing to forgive his antics, the pair began dating when Harry went back to Afghanistan in September, sending letters to and fro.

When Harry returned in 2013, the pair took romantic skiing holidays, Harry spent long weekends with Cressida’s family and they attended Glastonbury together that summer.

The pair made their first official outing at Wembley Stadium in March 2014.

Harry and Cressida made their first official outing in March 2014 at Wembley Stadium [Photo: Getty]

Having dated for just over a year, press were already penning Cressida a royal bride-to-be and an engagement announcement was expected imminently.

But later that year, Cressida cut off the relationship.

Nicholl explains in her book that her decision was bread from a mixture of reasons: she had realised she was far from ready to lead a royal life, wathcing footage of Kate’s royal tour of Australia had “spooked” her (according to a friend) and she still had feelings for her ex, Harry Wentworth-Stanley.

Cressida with Princess Eugenie (Harry’s cousin) at a wedding in 2013 [Photo: Getty]

Introducing Meghan Markle

Two years later, a blind date lead Harry to Meghan Markle.

Set up by a mutual friend – who was first suspected to be fashion designer Misha Nonoo, but is now thought to be Violet von Westenholz, the daughter of a friend of Prince Charles – Harry and Meghan met for a drink in July 2016. 

Meghan Markle in Season 1 of lawyer drama Suits. [Photo: Getty]

The attraction was instant. “The beautiful woman tripped and fell into my life and I fell into her life,” Harry said. 

The pair vouched to free-up their schedules and met up a handful more times before Harry whisked Meghan away to Botswana for a romantic getaway, barely a month after their first meet. 

This was their first long period alone (five days) and from then on the pair were inseparable.

Press first caught wind of Meghan when The Sunday Express reported Harry was secretly dating the American ‘Suits’ actress.

Click below for everything you need to know about Harry’s bride-to-be…

Harry confirmed his romance in November 2016 by releasing a rare statement with a plea to the media and social media trolls to stop the “wave of abuse and harassment” his new girlfriend was facing. 

Soon after, In January 2017, Meghan reportedly was introduced to the Duke and Duchess of Cambridge and Princess Charlotte.

The pair played out the rest of the year with a series of secret meetings, a public kiss at a polo match, a three-week holiday for Meghan’s birthday in Botswana, a rendezvous at Pippa Middleton’s wedding reception, and for Meghan, a cover story with Vanity Fair.

We’re two people who are really happy and in love,” she told the publication. 

Harry and Meghan watch the wheelchair tennis at the Invictus Games in September 2017 [Photo: Getty]

In September 2017, the pair put on their first display as a couple, walking hand-in-hand to watch the wheelchair tennis at the Invicitus Games in Toronto. 

On 27 November 2017, after days of buzz in the press that an engagement was imminent, Clarence House announced the engagement of Harry and Meghan and the pair stepped out at Kensington Palace to pose for photos. 

Newly engaged Prince Harry and Meghan Markle pose for photos at Kensington Palace [Photo: Getty]

Currently, Harry and Meghan are living in Nottingham Cottage on the grounds of Kensington Palace as they gear up for their wedding on May 19th.

The pair are due to marry at St George’s Chapel, Windsor Castle in what will be the wedding of the year.

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