Prince Harry, the Duke of Sussex, has had a tumultuous history when it comes to relationships, with his romantic entanglements often playing out in the public eye. In fact, just a decade ago, many would have predicted that he’d end up marrying Chelsy Davy, one of his most well-known exes. However, despite their on-again, off-again relationship, it seems Harry’s desire to start a family ultimately led him down a different path.

According to Victoria Arbiter, 9Honey’s royal correspondent, Harry had been desperate to settle down and have children for years. He even expressed his enthusiasm around kids, hinting at his potential to be an excellent father.

But finding someone willing to take on the challenges that come with being a royal partner proved difficult. That is until he met Meghan Markle, who will soon become the Duchess of Sussex when they tie the knot on May 19.

Before then, let’s take a trip down memory lane and explore all the women who could have potentially been the future Duchess of Sussex.

Natalie Pinkham

British television presenter, who met Prince Harry in 1999 and later found themselves at the center of a media storm, has spoken out about their friendship over the years. Initially linked to the royal in 2003 following a night out on London’s party scene, Pinkham was adamant that there was nothing romantic between them, with Harry still dating Chelsy Davy at the time. In fact, Pinkham went so far as to assure the media that Harry’s then-girlfriend had ‘nothing to worry about.

‘ Fast forward to 2006 and Pinkham took to the press once more, this time to reiterate their platonic bond. Little did they know, however, that a few years later they would find themselves at the center of another high-profile controversy – the infamous groping photo scandal. Involving Pinkham and Harry, the images were first published without permission by The Sun, prompting an apology from the publication shortly after.

Cassie Sumner

In 2004, Prince Harry’s social life took center stage when he was spotted with glamour model Cassie Sumner after meeting at the popular nightclub Chinawhite. According to Sumner’s own account of their brief encounter, Harry had initially been seen with another glamour model, Lauren Pope, before shifting his attention to her. At the time, 21-year-old Sumner and 19-year-old Harry were just starting out on their relationship, which she described as a ‘normal night out’ for a young single person.

Catherine Ommanney

In 2006, Catherine Ommanney’s name became linked to Prince Harry, sparking controversy surrounding their secret affair. At the time, Harry was just 21 years old, while Ommanney was 34. In a candid confession, the star of The Real Housewives of D. C. revealed that their brief romance involved some intimate moments and flirtatious text messages, but ultimately fizzled out after just a few days.

Interestingly, despite being single at the time, Ommanney’s affair with Harry occurred while he was still romantically entangled with Chelsy Davy.

Chelsy Davy

Harry’s longest relationship was with Chelsy Davy, a Zimbabwean solicitor-turned-jewellery designer whom he dated on-and-off from 2004 to 2011. The pair first met in Cape Town through mutual friends and had a complex relationship marked by periods of romance and separation. Despite the ups and downs, Chelsy remained a constant presence at significant events, including Prince William’s wedding to Kate Middleton in 2011.

In a candid interview with The Times in 2016, Chelsy described her experience with Harry as ‘normal kid’ stuff, but acknowledged that the intense media scrutiny was often overwhelming, describing it as ‘crazy and scary and uncomfortable’. She revealed that coping with the negative attention was particularly challenging for her.

Natalie Imbruglia

Astrid Harbord

While the world may have been fixated on the royal family’s inner circle, little did they know that Harry was quietly building connections with his own socialite set. In 2009, he was spotted letting loose in Chelsea with Astrid Harbord, a longtime pal of Kate Middleton’s. The Chelsea native even got an exclusive invite to Clarence House while Charles and Camilla were out of town, a rarefied experience that would have been the envy of many.

Despite the initial spark, their bond ultimately evolved into a strong friendship rather than romantic entanglement.

Caroline Flack

Camilla Romestrand

When Harry’s relationship with Chelsy was on hiatus again, he found himself linked to Camilla Romestrand, the lead singer of Norwegian rock band Eddie The Gun. Insiders reveal that during their time together, Camilla would often spend the night at ‘the Palace’ – a clear indication of the level of intimacy they shared. According to reports, Harry was a perfect gentleman, even going as far as bringing Camilla breakfast in bed.

However, it seems that their romance eventually fizzled out due to the significant distance between them.

Florence Brudenell-Bruce

Following his official split from Chelsy Davy, Harry’s love life took a new turn when he started dating lingerie model Florence Brudenell-Bruce in the summer of 2011. The whirlwind romance came to an abrupt end when Harry reportedly prioritized his helicopter training and desire for freedom over commitment. His reluctance to settle down was likely fueled by his impending return to Afghanistan, where he would continue serving his duty.

Cressida Bonas

Harry’s relationship with actress Cressida Bonas was sparked by his cousin Princess Eugenie, and the pair began dating in 2012. Their time together lasted until 2014, when they parted ways reportedly due to the intense media scrutiny they faced. According to royal expert Ingrid Seward, who is also a friend of Cressida’s mother, the actress struggled to cope with the constant public criticism, feeling that she was being unfairly targeted.

As Ingrid recalled, Cressida found it difficult to deal with the negative attention, saying ‘why are they getting at me?’

Mollie King

In 2012, Harry and Mollie King, a member of The Saturdays, embarked on a brief romance that was sparked by their friendship. Having been acquainted for about two years prior, the pair’s relationship blossomed as they were frequently spotted around London’s nightlife scenes. Nonetheless, their romance was short-lived, with Harry ultimately ending things due to concerns that Mollie seemed to be overly enamored with the publicity surrounding their relationship.

Ellie Goulding

The whispers of a romantic connection between Prince Harry and Ellie Goulding began circulating in 2016 following their alleged flirtation at the Audi Polo Challenge. Although the two were initially introduced at Prince William’s wedding, they have maintained a strong friendship over the years. Interestingly, Ellie was reportedly invited to Harry’s royal wedding to Meghan Markle, along with other close friends such as Chelsy and Cressida.