It's been more than a decade since Prince Harry and Chelsy Davy first met – and their connection has its roots in Harry's beloved Africa

By Diana Pearl
Updated September 09, 2015 11:00 AM
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Shaun Botterill/Getty

He says he’s content being single, but Prince Harry did say that he’d “love to have kids right now” and that “it would be great to have someone else next to me to share the pressure.” Is it possible that he may have found that someone more than a decade ago?

As Prince Harry, 30, prepares to return home after a months-long conservation trip to Africa, reports have linked him once again to his ex-flame Chelsy Davy, 29.

Here, a look back at their out-of-Africa romance – and why the Zimbabwe-born lawyer may still be in the picture.

Harry first met Chelsy in 2004 in Africa in between finishing his studies at Eton and starting his military training at Sandhurst while he was pursuing a gap year. Rumor has it that Harry fell for Davy, the daughter of a Zimbabwean billionaire, within days.

Back when the then- Kate Middleton and Prince Williamwere off, Chelsy and Harry were on. At the Concert for Diana that William and Harry hosted in 2007 in honor of their mother, Chelsy sat next to Harry in the front row, while Will and Kate, who had split a few months prior, on their way towards a reconciliation.

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A guaranteed activity for a royal girlfriend? Plenty of afternoons spent watching polo. In 2006, Chelsy laughed on the sidelines with Princess Kate (then Kate Middleton).

Despite the high-profile nature of their relationship, Harry and Chelsy weren’t the type to entirely shy away from PDA. While on a visit to St. John in the British Virgin Islands, the two cuddled up – and shared a kiss – at a match during the World Cup Cricket.

Sitting beside Prince William, Davy watched as Harry was given a campaign medal for his service in Afghanistan in May 2008. That same month, she made her official debut at a royal function for the wedding of Harry’s cousin Peter Phillips to Autumn Kelly.

Later in 2008, the two were all smiles at a rugby match in London. However, it wasn’t all smooth sailing for the couple after that: They split in early 2009, only to reunite at the end of the year.

In May 2010, the two appeared together in public with Prince Charles in 2010, when Harry was awarded his helicopter pilot’s wings. At the ceremony, onlookers saw her chatting with Harry’s stepmother, Camilla, the Duchess of Cornwall and giving the Princes of Wales a friendly kiss. However, despite these warm interactions with both Harry and his family, the relationship was heading for a break. Later that month, they broke up.

With wedding bells ringing for his brother, perhaps Prince Harry was eager to reconnect a love of his own. He invited her to be his date to the 2011 wedding of Prince William and Princess Kate. The reunion, however, didn’t last long. By the end of the summer, the two were off – seemingly for good. Davy was reportedly wary of marrying into the royal family, a sentiment she still feels today: A family friend told PEOPLE that “She’s her own woman”.

The two have been “off” for the past four years, and they’ve both been dating other people in the meantime (including Harry’s most recent ex, actress Cressida Bonas). However, dating for six years means the two have plenty of mutual friends, so their paths have crossed, including at the wedding of Thomas Van Straunbenzee (one of Princess Charlotte‘s godparents!) and Melissa Percy, where Chelsy was a bridesmaid, for example.

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