Prince Harry’s path to finding lasting love has been one of the most closely watched royal romance stories of the modern era.
As the youngest son of King Charles III and the late Princess Diana, Harry’s journey through relationships has been marked by intense media scrutiny, the unique pressures of royal life, and a continuous search for authentic connection.
Before meeting Meghan Markle in 2016, Harry’s dating life was characterized by a series of relationships that ultimately faltered under the weight of royal expectations and media attention.
The prince, known for his candid nature and rebellious spirit, faced unique challenges in finding a partner who could both handle the intensity of royal life and maintain their own identity within it.
Currently, Harry resides in California with his wife Meghan and their two children, Archie Harrison and Lilibet Diana, having stepped back from senior royal duties in pursuit of a more independent life.
This current chapter represents a dramatic departure from his earlier romantic experiences and reflects the lessons learned from his dating history.
Early Relationships (2003-2004)
Natalie Pinkham: The First Public Link
The story of Harry’s dating life begins with TV presenter Natalie Pinkham, whom he first met at the 1999 Rugby World Cup. Their romantic connection reportedly blossomed in 2003, when Harry was just 19 years old.
The relationship, while never publicly confirmed by either party, marked one of Harry’s first experiences with media attention on his personal life.
Pinkham, who later became a reporter for Sky Sports F1, demonstrated early on what would become a pattern in Harry’s relationships – the ability to maintain a friendship even after any romantic connection ended.
As she once remarked, “I realized very quickly what a normal bloke he was,” offering an early glimpse into Harry’s desire to be seen as more than just his royal title.
Cassie Sumner: The Nightclub Encounter
In 2003, at London’s Chinawhite nightclub, Harry had a brief encounter with Cassie Sumner that would later make headlines.
Sumner, who was 21 at the time while Harry was 19, shared a detailed account of their evening with the press.
According to her story, “He made eye contact as I stood at the bar with friends and invited me to join his private table. It wasn’t long before he began cuddling up to me.”
The incident, while brief, highlighted the challenges Harry would face in maintaining privacy in his personal life.
Sumner’s candid revelation to the press would be one of many instances where Harry’s private moments became public fodder.
The Challenges of Dating as a Young Royal
These early experiences set the stage for what would become recurring themes in Harry’s dating life: the difficulty of maintaining privacy, the challenge of distinguishing genuine interest from opportunistic attention, and the constant presence of media scrutiny.
As a young royal in the early 2000s, Harry was attempting to navigate normal young adult relationships within the abnormal constraints of his position.
The Chelsy Davy Years (2004-2011)
First Meeting in Cape Town
The most significant early relationship in Prince Harry‘s life began during his gap year in Cape Town in 2004. Chelsy Davy, daughter of a Zimbabwean billionaire, caught Harry’s attention almost immediately.
In his memoir “Spare,” Harry recalls their first connection vividly: “I remembered her being… Different. Unlike so many people I knew, she seemed wholly unconcerned with appearances, with propriety, with royalty.”
He describes their “first kiss under the stars,” marking the beginning of what would become his longest relationship.
The On-and-Off Relationship Timeline
Their relationship spanned nearly seven years, characterized by periods of intense closeness and several breakups. Davy even pursued a law degree at Leeds University to be closer to Harry.
The couple shared many significant moments, including:
- Davy attending Prince Charles’ 60th birthday celebration
- Her presence at Princess Diana‘s memorial service on the 10th anniversary of her death
- Meeting Queen Elizabeth II at a society wedding
- Attending numerous official royal functions together
The relationship weathered multiple separations, including a notable break in 2009, before reconciling.
Their connection was deep enough that Davy was even invited to help edit Harry’s best man speech for William and Kate’s wedding in 2011, where she advised him to remove some racier elements, including a reference to Kate’s “killer legs.”
Integration into Royal Life
Davy became increasingly integrated into royal life during their relationship. She met the Queen, attended royal functions, and was often seen at polo matches supporting Harry.
She was even present when Harry received his helicopter pilot’s wings in May 2010, a significant moment in his military career.
Reasons for Their Ultimate Separation
The pressure of royal life ultimately proved too overwhelming for Davy.
As she later revealed to The Times: “It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn’t cope.”
The intensity of media scrutiny became particularly problematic, with Harry revealing in his memoir that paparazzi had even placed a tracking device under her car.
The Queen’s Influence
In “Spare,” Harry acknowledges that his grandmother’s opinion played a role in the relationship’s end.
He wrote that he “couldn’t help” but think about what the Queen thought of Davy’s free-spirited lifestyle.
“I loved Chels’ ease, that she wasn’t complicated… She wore miniskirts and high-heeled boots, danced however she wanted, drank tequila like me, and all of this made me really happy. I couldn’t help what my grandmother thought about it.”
Their Final Parting
The relationship’s end was marked by mutual understanding but also deep emotion. Harry poignantly writes in “Spare”: “The day I got my wings, I figured she got hers.”
Prior to Harry’s wedding to Meghan Markle in 2018, the former couple shared what Vanity Fair described as an emotional “parting” phone call.
A source revealed: “It was their final call, a parting call in which they both acknowledged Harry was moving on.
Chelsy was quite emotional about it all, she was in tears and almost didn’t go to the wedding.”
Brief Encounters and Rumored Romances (2009-2011)
Astrid Harbord: The Society Connection
During one of his “off-again” periods with Chelsy Davy in 2009, Harry was briefly linked to Astrid Harbord, a notable connection as she was a friend of Kate Middleton‘s.
According to News of the World, the pair’s connection became public after they were spotted spending an evening at a London club before returning to Clarence House at 3 a.m.
The brief liaison highlighted Harry’s social circles overlapping with those of his brother’s future wife.
Caroline Flack: The TV Presenter
The late Caroline Flack’s connection with Harry in 2009 became one of his more publicly discussed brief relationships.
In his memoir “Spare,” Harry speaks openly about their time together, describing her as “funny and sweet and cool.”
The relationship began after they were introduced by mutual friend Natalie Pinkham.
Flack revealed in her autobiography “Storm in a C Cup” that the relationship ended almost as soon as it became public knowledge: “Once the story got out, that was it. 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.”
In “Spare,” Harry reflects that they “continued to see Flack, on and off, but we didn’t feel free anymore… the relationship was tainted, irredeemably, and in time we agreed it just wasn’t worth the grief and harassment.”
Mollie King: The Pop Star
The English singer and member of girl group The Saturdays, Mollie King, entered Harry’s life around 2010.
Their first meeting occurred at the Asprey World Class Cup at Surrey’s Hurtwood Polo Club.
King confirmed the brief relationship to Closer magazine, stating, “Yes, I have met Harry, and we did go out for a drink.”
However, the relationship reportedly ended because King was too open about their connection.
Sources suggested that Harry broke things off because she was too willing to discuss their relationship with the public, highlighting his growing sensitivity to media exposure in his personal life.
Florence Brudenell-Bruce: The Model
In 2011, following his final split from Chelsy Davy, Harry was linked to model and actress Florence Brudenell-Bruce, a daughter of the Earl of Cardigan and cousin of English singer Bo Bruce.
Their relationship was characterized by discretion, with the pair reportedly spending time at her London home in Notting Hill in what the press termed “secret trysts.”
When questioned about the relationship, the Palace maintained their standard response: “We don’t comment on the Prince’s personal life.”
However, according to the Daily Mail, it was Brudenell-Bruce who ended the brief relationship, with a source revealing, “She felt he had a wandering eye all the time and she wasn’t really into not knowing who he was flirting with or talking to when they were apart.”
She later married multimillionaire banker Henry St George.
The Impact of Media Attention
This period of Harry’s dating life clearly demonstrated the overwhelming impact of media attention on his relationships.
Each of these brief romances followed a similar pattern: initial private connection, media exposure, and swift conclusion.
The constant scrutiny made it nearly impossible for natural relationships to develop, with potential partners either embracing the publicity (leading to Harry’s withdrawal) or being overwhelmed by it (choosing to withdraw themselves).
The Cressida Bonas Period (2012-2014)
Introduction through Royal Cousins
Cressida Bonas, Harry’s second most serious relationship, came into his life through royal family connections.
She was introduced to Harry by his cousins, Princess Eugenie and Princess Beatrice, in 2012.
Coming from an aristocratic background as the daughter of former It girl Lady Mary-Gaye Curzon and half-sister of Isabella Anstruther-Gough-Calthorpe, Bonas seemed well-positioned to understand the complexities of high society life.
Their Time Together
The relationship quickly became serious, with both William and Kate apparently approving of the match.
In “Spare,” Harry reveals that “both the Prince and Princess of Wales had mentioned, pointedly, repeatedly, how much they liked Cressida.”
Their relationship marked a period of emotional growth for Harry, who shares in his memoir a particularly vulnerable moment: “This is the first time I’ve been able to cry about my mum since the burial.”
The couple’s two-year relationship was marked by genuine connection and mutual understanding.
Bonas, an actress and sometimes model who worked with prestigious brands like Burberry and Mulberry, brought her own accomplishments and identity to the relationship.
Struggles with Public Life
Like many of Harry’s previous girlfriends, Bonas struggled with the intense public scrutiny that came with dating a prince.
The pressure of media attention and the constraints of royal protocol proved challenging for someone who valued her independence and privacy.
The relationship reportedly ended because Bonas couldn’t stand the public scrutiny of being with Harry, a theme that had become familiar in his romantic life.
The Breakup and Aftermath
When the relationship ended in 2014, both parties maintained their dignity and privacy.
However, when news broke of Harry’s engagement to Meghan Markle, Bonas posted what many interpreted as a cryptic message on Instagram: “No matter how educated, talented, rich or cool you believe you are, how you treat people ultimately tells it all.”
Despite any potential tension, Bonas maintained connections with the royal family, attending Harry’s wedding to Meghan Markle in 2018.
She has since married Harry Wentworth-Stanley and welcomed a son, suggesting that both she and Prince Harry found their own paths to happiness.
Final Dating Years (2015-2016)
Ellie Goulding: The Last Rumored Romance
Before meeting Meghan Markle, Harry’s last publicly rumored romance was with pop star Ellie Goulding.
Their connection had royal roots – Goulding had performed at Prince William and Kate Middleton‘s wedding reception at Buckingham Palace in 2011 and later at Harry’s Invictus Games in 2014.
In 2015, reports surfaced of Harry and Goulding getting cozy at a polo match in Berkshire.
According to various accounts, they were spotted “canoodling” under blankets and were later allegedly seen kissing, though no photographic evidence ever emerged.
The singer maintained a diplomatic silence about the nature of their relationship, offering only a mischievous grin when questioned about the prince on camera.
Finding Meghan (2016-Present)
The Blind Date That Changed Everything
In early July 2016, Harry’s life changed forever when a mutual friend set him up on a blind date with American actress Meghan Markle.
Unlike his previous relationships, this connection quickly evolved into something deeper and more serious.
Within months of dating, Harry took an unprecedented step by releasing a rare public statement urging the media to stop harassing Markle and her family, showing a new level of protectiveness and commitment.
The couple managed to keep their early relationship relatively private, though they did share significant moments together, including a weeks-long African safari holiday.
This echoed Harry’s previous pattern of taking serious girlfriends to Africa, but this time felt different to those close to the prince.
A Different Kind of Relationship
What set Meghan apart from Harry’s previous relationships was her ability to handle the public scrutiny while maintaining her own identity.
After meeting the Queen and receiving her approval, the couple announced their royal engagement.
Their wedding on May 19, 2018, marked not just a personal milestone but a historic moment for the British monarchy.
Marriage and Family Life
Harry and Meghan’s relationship has produced two children: Archie Harrison, born in 2019, and Lilibet Diana, born in 2021.
Their family life has taken a dramatically different path from traditional royal expectations, with the couple choosing to step back from senior royal duties in 2020.
Breaking Away from Royal Traditions
In perhaps the most dramatic departure from his previous relationships, Harry’s marriage to Meghan led to a complete reimagining of his role within the royal family.
The couple now resides in California, having chosen to prioritize their family’s privacy and independence over royal obligations.
