Inside Prince Harry's Relationship History

Prince Harry is a one-woman man now, but the British prince was once as notorious for his womanizing inclinations as he was for his revelrous night-outs. Women from some of London's snazziest circles were linked to Harry throughout his youth, and details of his private affairs keeping tabloid front pages and media cycles forever engaged. This was often to disastrous effect, as the royal has strongly reiterated on several occasions. 

Testifying in his case against British tabloids in 2023, he said: "At no point did I have a girlfriend or a relationship with anyone without the tabloids getting involved and ultimately ruining it," referring to the press as the "third party" in his past love affairs (via the Independent). While his wife Meghan Markle is the freshest target in public memory, those who remember know that a long list of women precedes her. 

During his bygone days as the party prince of London,  there was seldom a moment that Harry's relationship status was set at single. From alleged flings with models and singers to profound romances that find a mention in his tell-all memoir "Spare," a multitude of rumored and confirmed liaisons populated Harry's life before he settled down for good. Though Meghan and Harry's subversive fairytale is lauded for setting modern standards of love — even going so far as to challenge the British monarchy — the "Suits" star wasn't the only woman with whom Harry found a meaningful partnership worth preserving. On that note, let's dive into Prince Harry's relationship history.

Prince Harry had a short romance with Natalie Pinkham

One of the earliest rumors surrounding Prince Harry's dating life linked him up with British television presenter Natalie Pinkham in 2003. While the alleged romance was never confirmed by either party, their longtime friendship that preceded the dating rumors was no secret. "They enjoy one another's company and it's probably the case that when they first met, Harry had a bit of a crush on Natalie, but she never saw him in that way," a friend of Pinkham's told the Daily Mail, while another royal insider tagged her as "one of Harry's favourite drinking buddies." 

The supposedly platonic nature of Harry and Pinkham's relationship, however, came under question in 2006 after The Sun published a picture of Harry fondling and kissing Pinkham, with a headline that screamed "Dirty Harry" (via New Zealand Herald). The photo, which also featured Prince William in the background, sparked controversy — especially since Harry was reported to be dating Chelsy Davy at the time. 

Pinkham reportedly reached out to Davy to clear the air around the photo, which she claimed could only have been leaked by a friend. That didn't deter her from losing faith in her own friendship with Harry though. Not long after his split from Davy in early 2009, The Telegraph reported that the prince relied on Pinkham for support. "Natalie is one of his oldest and best friends and will always be there for him when he's feeling down," a source said. 

Things got hot between him and Cassie Sumner

Prince Harry's roving romances were a significant aspect of his legendary youth. His hard-partying lifestyle was notorious around London's nightclubs, where the renegade prince is known to have indulged in amorous adventures. One such outing was rumored to have been with model Cassie Sumner, who was a fixture in men's magazines and the city's buzzing party scene. According to Mirror, one night back in 2004, Harry locked eyes with Sumner at the erstwhile celebrity-favorite club Chinawhite and scarfed down several drinks with the bombshell. Then still a teen, he allegedly got touchy-feely with the model a few years his senior and in Sumner's words apparently: "He was undressing me with his eyes." 

Prince William had supposedly also been at the party but left earlier than his seasoned reveler of a brother. "It's not every day you have a real-life Prince Charming coming on to you. Harry was up for a party — big time," the tell-all account from Sumner mentioned. The outlet reported that Harry had been having fun with another model, Lauren Pope, earlier that evening — a detail Sumner apparently knew but didn't mind (possibly because she ultimately concluded that she didn't fancy him). While Harry has never explicitly addressed the incident, Town & Country postulated that he alluded to it in "Spare," recounting his night with a "page-three girl" and the "frantic commentary about the horrors of the Spare dating ... such a fallen woman." 

He had a long-term on-again, off-again relationship with Chelsy Davy

The only other name in Prince Harry's list of sweethearts that comes close to the import Meghan Markle's holds is presumably Chelsy Davy's. The British prince spent a significant part of his youth with the Zimbabwe-born businesswoman between 2004 and 2010, pictured alongside her at royal engagements, sports matches, holidays — basically all over the place. Their love story began in Africa, a place close to both their hearts. In "Spare," Harry wrote about reconnecting with Davy in Cape Town years after having met her at a polo club. "Unlike so many girls I met, she wasn't visibly fitting herself for a crown the moment she shook my hand," he reminisced (via Just Jared). They couldn't help but kindle a romance. 

Their fairytale continued as Harry reported for military duty, even though media reports speculated otherwise. Although their relationship was weighed down by trials ranging from separation periods to even a temporary breakup in 2009, Harry and Davy managed to power through most ordeals — except that of unbridled press attention. As Davy later told The Times: "I couldn't cope. I was young, I was trying to be a normal kid and it was horrible." Harry also echoed the fears that plagued the young couple while testifying in his hacking case against Mirror Group Newspapers in 2023. The couple went their separate ways in 2010, though Harry admitted to having to work through some unresolved feelings for months after. 

He was briefly linked to his sister-in-law's friend Astrid Harbord

To fill the Chelsy Davy-sized hole in his heart when the couple briefly broke it off in 2009, Prince Harry allegedly turned his attention to Astrid Harbord. A well-known face in Britain's elite social circles and most notably a friend to Princess Catherine, Harbord was spotted out and about in London with the young royal more than once, sparking rumors of a fling between the two. The gossip made its way down the grapevine after extinct paper News of the World claimed that the two indulged in a revelrous night at Raffles, before heading back to Clarence House at a late hour (via The Telegraph). Photographs of the pair together in a car were splashed across tabloids. 

Living up to her reputation as a hard partier, Harbord also accompanied Harry to a rave scene in East End a few weeks later, according to the Daily Mail. "Astrid is quite a party animal. The rave was due to end at 5 a.m., so it was noticeable that she left with Harry around 1:30 a.m.," a source told the outlet. Harbord's denial of a budding romance with Harry was also reported, but it didn't help in quashing the dating rumors that surrounded them for a while. It could have just been a fleeting liaison, since Harbord — who has on occasion been counted among Harry's closest friends — doesn't find a mention in "Spare," as some of his other more significant former girlfriends do. 

Media attention troubled his relationship with Caroline Flack

During a break in his relationship with Chelsy Davy, Prince Harry also briefly hooked up with television presenter Caroline Flack in 2009. Interestingly, it was through one of Harry's old flames Natalie Pinkham that the couple met at a dinner party. For Flack, the prospect of meeting Britain's royal scion was nothing short of exciting. Detailing their first encounter in her 2015 memoir "Storm in a C-Cup," she wrote: "I was just sitting there and he arrived with a few others in tow and we all spent the evening chatting and laughing."  A romance blossomed, but before it could fully bloom, it was over. 

The ever-present media attention around the couple's life was overwhelming — a point Harry raised during his phone hacking case against Mirror Group Newspapers in 2023. He recalled in particular an incident of meeting Flack for a dinner date, only to find press photographers already there waiting for them. "The evening was specifically between me Caroline who is no longer with us," he stated (via the BBC). 

Flack died by suicide in 2020, with the burgeoning press scrutiny around her life widely cited as a factor in the tragedy. Harry too, adjudged the situation similarly in his memoir "Spare" (via Us Weekly). "I can't forget how much she suffered for her fatal sin of going out with me," he wrote, denouncing the harassment and slurring the late television personality was subjected to at the hands of the press. 

He was rumored to be dating Scandinavian rocker Camilla Romestrand

Norwegian singer Camilla Romestrand was a one-time feature on Prince Harry's string of high-profile linkups. After his breakup from longtime girlfriend Chelsy Davy in 2010, rumor mills worked in overdrive to zero in on the British prince's next ladylove. Romestrand's name was thrown up by tabloids, with speculation around the nature of her relationship with Harry. The now-defunct British paper News of the World was reportedly instrumental in fanning this gossip, quoting a source who seemed to offer insight into Harry and Romestrand's alleged affair, per CBS News. "She talks about staying overnight at 'the Palace.' She says he was a 'total gentleman' but doesn't divulge much else," the anonymous commentator claimed, airing Romestrand's alleged anxieties over her career being overshadowed by her private affairs. 

Romestrand at the time was associated with the indie musical act Eddie the Gun, and while she didn't personally remark on the royal chatter surrounding her, her father rose to the occasion. He dismissed the affair, reportedly telling the Norwegian press (via Nettavisen): "This is just nonsense." Beyond tabloid buzz about Harry serving the singer breakfast in bed and hosting her at Clarence House, there was really nothing else to go on. As Vanity Fair aptly quipped on the matter: "Poor Prince Harry — seems he's automatically dating any woman he gets within 50 feet of, regardless of age." Romestrand's social media shows that she is now married and has two kids. 

He shared a love affair with Florence Brudenell-Bruce

If Prince Harry's inclusion of his girlfriends by name in "Spare" is a measure of the importance they held in his life, then Florence Brudenell-Bruce would rank well. In fact, they were supposedly compatible enough for the prince to stop and consider if she was "his person" (via Tatler). The model and actor, widely referred to as Flea in her social circles, met Harry in 2011 after his breakup from longtime girlfriend Chelsy Davy. They were introduced by mutual friends and spent a fun first evening together, concluding it at Brudenell-Bruce's house in Notting Hill where she invited the royal in for tea. 

"The weeks that followed were idyllic. We saw each other often, laughed a lot, and no one knew," Harry gushed in his memoir, per Town & Country. Their bliss didn't last too long unfortunately, with Brudenell-Bruce getting a taste of the press scrutiny that came with being Harry's ladylove. "She said she was under twenty-four-hour surveillance. Like some kind of criminal," he wrote. They called time on their relationship, an event that apparently affected the British prince profoundly. 

Brudenell-Bruce was no less hurt. But she appreciated the silver lining that came with the breakup. "Although it was sad at the time, I feel lucky that the relationship was short-lived," she wrote for The Telegraph, reiterating her unwillingness to live a hyper-public lifestyle. Soon after in 2013, she married multi-millionaire Henry St. George, with whom she shares two children. 

Harry and singer Mollie King briefly saw each other

Word on the street in 2012 was that Prince Harry was supposedly going out with singer-songwriter Mollie King. Rumors flew not long after King's breakup from her on-and-off model boyfriend David Gandy, and they intensified when she was reportedly spotted hanging out with the young prince at a club in London, per Hello! magazine. However, it seemed that the celebrity pair were not willing to make their private affairs public just then, because what followed was a series of dismissals and rebuttals from King.

"Everyone wants to believe it because he's royalty. Everyone would like it to be true but it's not. He's very out of my league," said The Saturdays singer during an appearance on BBC Radio 1 (via The Daily Beast). Even as she reiterated — in interviews and elsewhere on social media — that she only shared a platonic relationship with the British prince, tabloids ran ahead with speculation over Harry's keen emotions for her. 

It took a little while for King to seemingly get things off her chest — but she eventually did. In what was widely taken as a confirmation of their very brief but possibly real affair, King said in an interview later that same year: "Yes, I have met Harry, and we did go out for a drink" (via The Standard). After the Harry episode ended, King got back together with former flame Gandy for a while before finding love in English cricketer Stuart Broad.

Harry's cousin introduced him to Cressida Bonas

Cressida Bonas was one of Prince Harry's most notable paramours in his pre-Meghan Markle era. The actor features significantly in his memoir "Spare," where he details her role in helping him cope with the death of his mother, Princess Diana. Bonas and Harry were famously introduced to each other by the latter's cousin, Princess Eugenie, and after a bumpy beginning — that involved awkward first dates and a months-long separation — they became a hot item. 

From attending film premieres together to carousing at nightclubs, the couple painted London red for a good two years between 2012 and 2014. Though it was only towards the tail end of their relationship that the pair marked their first official engagement together at We Day UK 2014, their passion was a much-talked-about phenomenon. That was cited as part of the reason that Harry and Bonas parted ways. "She felt that the fame of her relationship put her 'in a box,'" Robert Lacey wrote in his book "Battle of the Brothers: William and Harry" (via Marie Claire). 

The royal life wasn't for Bonas. Yet, her companionship with Harry remained meaningful. She was apparently the first person to open Harry (and his tears) up about Diana's tragic death, an event he describes in "Spare" as cathartic (per Daily Express). He wrote, "It accelerated our bond, and added an element rare in past relationships: immense gratitude." Bonas eventually married her old flame from college, Harry Wentworth-Stanley. 

Popular singer Ellie Goulding was a one-time girlfriend of the prince

Ellie Goulding is no stranger to rubbing shoulders with England's elite — including the royal family. Besides having scored a personal invite to Prince William and Princess Catherine's wedding reception in 2011, the "Love Me Like You Do" hitmaker is particularly pally with Princess Eugenie. One of her most famous associations with the blue-blooded clan, however, is the one she allegedly had with her friend's cousin. Prince Harry and Goulding were rumored to be a thing after reports emerged of them enjoying each other's company at the Audi Polo Challenge in 2016. 

Quoting a source, The Sun noted that sparks were flying between them at the polo match after-party where "Harry and Ellie only had eyes for each other all night — they spent a lot of time sitting together under blankets." Harry had allegedly sought out Goulding's number in the days leading up to the event, which marked their first proper meeting. The two reportedly shared a kiss that night before parting ways. 

While Harry didn't address the speculation, Goulding blushingly relented. When asked upfront on Australian chat show "The Project" if she planned on having a baby with her rumored royal boyfriend, Goulding went red. "Why did I have a feeling that was going to come up? You naughty people," she replied, without divulging more (via Vanity Fair). Well, whatever transpired between them didn't last long, as the love of Harry's life was waiting just around the corner. 

Britain's rebel prince found forever love in Meghan Markle

Prince Harry's romantic escapades came to a seeming end in 2016, when Meghan Markle walked into his life — or rather, his Instagram. The young royal first encountered Meghan on a mutual friend's profile – wearing the dog ears filter, no less — and lost no time in making a move. "He called me last night dying to meet you," the friend texted Meghan, as shown in the Netflix documentary "Harry & Meghan." Instagram recons and texting translated into a date when the "Suits" star visited London for Wimbledon. 

Things moved fast then, with Meghan accompanying Harry to Africa after just two (clearly very successful) dates. "So then we were really by ourselves, which was crucial to me to make sure that we had a chance to know each other," the prince said during a speech at the United Nations in 2022 (via People). Their camping trip was also where Harry got the early impression that Meghan was his soulmate. 

Harry and Meghan tied the knot in 2018 — the first of many major life-altering events to come for Buckingham's rebel royal couple. Rumors of a rift within the monarchy's innermost circle soon swirled, while Meghan received the usual vicious press treatment Harry's past partners were subjected to. By 2020, they announced their decision to step back from royal duties. Their eventual exit from the United Kingdom pulled back the curtains on the alleged mistreatment they faced within the palace.