Who has Prince Harry dated? A look back at the Duke of Sussex's relationship timeline before Meghan Markle

Before Meghan Markle, the Duke of Sussex was involved in a few serious relationships

Prince Harry and Meghan Markle at Royal Ascot in 2018
(Image credit: Samir Hussein / Contributor / Getty Images)

Who has Prince Harry dated before tying the knot with Meghan Markle in 2018?

Everyone's doing a deep dive into the Duke and Duchess' personal lives now that the Harry and Meghan Netflix series is out in its entirety. Throughout the documentary, viewers learn shocking revelations, hear anecdotes from Harry and Meghan's friends and uncover new details about the couple's relationship and complicated exit from the royal family. 

Although there's a lot to take in—and a lot to learn about Prince Harry's future with the British Monarch—people are taking a step back in time to revisit some of his romances before Meghan Markle entered the picture. 

Who has Prince Harry dated before marrying Meghan Markle?

We all know how Harry and Meghan met now that their docu-series shed light on their first dates and LDR. The two are playful with one another on camera, and Prince Harry has genuinely sweet things to say about his wife and the mother of his two children, Archie and Lilibet.  

"So much of what Meghan is, and how she is, is so similar to my mum,” he said "She has the same compassion, the same empathy, she has the same confidence, she has this warmth about her."

Despite troubles in their union—the distance, the media harassment, the lack of privacy—Harry and Meghan managed to make it work. However, Harry claims his royal title was the reason his previous relationships came to an end.

"[I learned] the pain and suffering of women marrying into this institution. I remember thinking, 'How can I ever find someone who’s willing and capable to be able to withstand all the baggage that comes with being with me?"

Prince Harry and Natalie Pinkham (2003)

Considered Prince Harry's first "real" girlfriend, sports reporter Natalie Pinkham met the Duke of Sussex in 1999 at the Rugby World Cup, several years prior to their relationship. According to reports, they did not part ways on bad terms and remain friendly to this day. 

Prince Harry and Chelsy Davy (2004-2011)

One of the Duke of Sussex's longest relationships is allegedlly one of his most rocky. He and the former attorney—who now owns her own jewelry line—were on-again, off-again for roughly seven years before ultimately calling it quits. 

Reports claimed she was not comfortable in the limelight, but still has much respect for the Prince. In fact, they last crossed paths in 2020 before Prince Harry was bound for Canada, according to reports, and they had a friendly reunion. She also admitted to writer Dolly Alderton that "I think we will always be good friends," according to a profile in The Times

While the two were on hiatus throughout their seven-year journey, Prince Harry was briefly linked to Astrid Harbord (a friend of Kate Middleton's), Caroline Flack, Camila Romestrand, Mollie King and Florence Brudenell, but none of the courtships seem to have lasted any significant amount of time.

Cressida Bonas (2012-2014)

Prince Harry's cousins Princess Eugenie and Princess Beatrice and set him up with Cressida, an actor who also claimed that the spotlight on her dating life was a bit too much to contend with. Although it seemed like a fairly cordial split, onlookers were not ones to shy away from that mysterious quote she posted on Instagram shortly after Prince Harry and Meghan Markle's engagement. It's safe to say we'll never really know what transpired between the two.

In the wake of Harry & Meghan even the Prince's short-lived romances have garnered spotlight. 

Speculation about his friendship with singer Ellie Goulding, particularly in 2015, came into question, although there's really no evidence, only hearsay, to support the argument. (She performed at Prince William and Kate Middleton's wedding, as well as one of Prince Harry's Invictus Games.) 

Others have actually spoken out about the docu-series. Real Housewives of DC star, Catherine Ommanney, claimed to Piers Morgan, "I just don't know whether I’d actually even recognize him anymore personality wise because when I watched him [on] the show, I just thought, 'Why?’"

She added, according to Express, "He would never in a million years, back in those days, have ever been that person to do the show. Never."

She alleges they dated for two months in 2006. 

Both parts of the Harry & Meghan series are now available for streaming on Netflix. 

Danielle Valente
Digital News Writer

Need a TV show recommendation? Maybe a few decor tips? Danielle, a digital news writer at Future, has you covered. Her work appears throughout the company’s lifestyle brands, including My Imperfect Life, Real Homes, and woman&home. Mainly, her time is spent at My Imperfect Life, where she’s attuned to the latest entertainment trends and dating advice for Gen Z.

Before her time at Future, Danielle was the editor of Time Out New York Kids, where she got to experience the best of the city from the point of view of its littlest residents. Before that, she was a news editor at Elite Daily. Her work has also appeared in Domino, Chowhound, and amNewYork, to name a few. 

When Danielle’s not writing, you can find her testing out a new recipe, reading a book (suggestions always welcome), or rearranging the furniture in her apartment…again.