Prince Harry: These are all the women he has dated, from Chelsy Davy to Meghan Markle

Prince Harry, the youngest of King Charles III and Princess Diana was born in 1984 in London. Though he is no longer a working royal, Prince Harry remains 5th in line to the throne of England.

Throughout his life, Prince Harry has gone through many ups and downs. Firstly, in 1992, his parents announced they were separating. At the time he was only 8 and, while his parents continued to attend functions together, they were very much living separate lives. Then in 1994, his father admitted to being unfaithful to his mother in an interview for ITV.

When asked by journalist Jonathan Dimbleby if he had been ‘faithful and honourable’ during his union to Diana, then-Prince Charles answered:

Yes, until (the marriage) became irretrievably broken down, us both having tried.

Following that shocking admission, Princess Diana also sat down for an interview, this time in 1995 and with the BBC. The Panorama interview is now an iconic moment of pop culture and a real testament to the ever-lasting aura of the Princess. In the interview, which has a very controversial history, Diana revealed some pretty shocking things as well.

Notably, she admitted to her own entanglement with James Hewitt. Furthermore, she commented on the affair Charles had with Camilla and acknowledged that she had known for a while:

There were three of us in this marriage, so it was a bit crowded.

After those very public revelations, Prince Harry’s parents finally agreed to get divorced and it was finalised in August 1996. A year later, Princess Diana died in a car crash in Paris while she was being chased by paparazzi. Images of Prince Harry and his brother walking behind their mother’s casket moved the world and the nation adopted the two boys.

As time went on, Prince Harry grew up in front of the world and his mistakes as well as personal life were broadcasted, scrutinised and analysed. Long considered the troublemaker of the family, Prince Harry seemed to have encouraged this image with his rather dishevelled love life. Let’s have a look at the women he has dated (for real and rumours), and married.

Linked to TV presenter Natalie Pinkham

Television presenter Natalie Pinkham has carved a significant niche for herself in the world of sports broadcasting, notably within the Formula 1 sphere. Born on September 20, 1977, in Buckinghamshire, England, Pinkham has been a familiar face at grand prix races as a pit lane reporter for Sky Sports F1. Beyond her F1 coverage, she has expanded her repertoire to include presenting at events such as The Isle of Man TT and the Goodwood Festival of Speed, alongside hosting segments for Chelsea FC and helming her podcast In The Pink, where she delves into the lives and careers of various individuals, including prominent figures like Damon Hill and Sir Chris Hoy.

Before her television career took off, Pinkham pursued a degree in politics at the University of Nottingham. Her professional journey in F1 began with BBC Radio 5 Live, before she joined Sky Sports in 2012. Pinkham's dedication and expertise culminated in her becoming the first woman to commentate on a Formula One session on British television during the 2021 Bahrain Grand Prix. Her role involves not just commentating but also conducting crucial interviews in the pit lane, providing fans with insider perspectives from drivers and team members alike.

Pinkham's personal life has also been of interest to the public. She was linked to Prince Harry in the early 2000s. According to Harper’s Bazaar, the two never confirmed a possible romance but they have ‘maintained a friendship’ over the years. In 2009, when Prince Harry broke up with Chelsy Davy, he allegedly called Natalie. Writing for The Telegraph, Richard Eden quoted one of her friends who said:

Natalie spoke on the phone with Harry and was happy to offer her support,

Natalie is one of his oldest and best friends and will always be there for him when he's feeling down.

The friend continued to give details to Eden:

Natalie and Harry have stayed friends through thick and thin,I think it has caused some tension between him and Chelsy in the past, but Natalie had nothing to do with their split.

However, it's her marriage to Owain Walbyoff, Managing Director at Endemol Games, that has marked a significant chapter in her life. The couple, who share two children, celebrated their union in a picturesque ceremony in Portugal, attended by notable figures including Zara Phillips and sports presenter Kirsty Gallacher. Natalie's choice of a Beulah gown for the occasion reflected her desire for something ‘feminine and floaty,’ a departure from conventional bridal attire.

As Pinkham continues to break barriers in sports journalism and maintain a balanced personal life, her estimated net worth of over £1 million and reported annual salary of over £100,000 underscore her success in a competitive field.

A night of flirtation with Cassie Sumner

In the early 2000s, Sumner found herself amidst the glitz and glamour of London's party scene, making headlines for her involvement with prominent figures, including a brief but widely publicised encounter with Prince Harry in 2004. The incident, occurring at the Chinawhite nightclub when Harry was 19 and Sumner was 21, became a subject of considerable tabloid speculation. Sumner recounted a night of flirtation and fleeting intimacy, capturing a moment that epitomises the wilder days of both their lives.

In 2023, Daily Star brought the story back in one of their articles. In it they explain that Sumner herself spoke about the experience. In her own words:

He was undressing me with his eyes

She added that before he came up to her, the royal was ‘snogging’ Page 3 model Lauren Pope. She continued:

I knew he'd been snogging Lauren earlier in the night but after she left he just honed in on me.

He seemed fascinated with my breasts, because he spent more time looking at them than he did my face when we talked.

Without discrediting Sumner's story, Prince Harry has never addressed and confirmed her story nor has anyone else.

However, Cassie Sumner's life story extends far beyond a single night's encounter with royalty. Her autobiography, Cassie Sumner: Loving It, released in 2008, reveals a woman who has navigated through the complexities of fame, personal despair, and recovery. Sumner's early success as a model introduced her to a world brimming with opportunities but also fraught with pitfalls, including substance abuse and the darker aspects of the entertainment industry. Her relationship with footballer Celestine Babayaro emerges as a turning point, helping her find her footing again in the world of modelling and away from the temptations that once led her astray.

Rumoured fling with Catherine Ommanney

Who is Catherine Ommanney?

Catherine Ommanney is a British reality TV star and interior designer who has experienced a whirlwind of media attention. She participated in the American TV showThe Real Housewives of D.C. She moved to the United States in 2008 and rose to fame on the reality series after marrying her second husband, Charles Ommanney.

Ommanney revealed that being on The Real Housewives forced her to face some challenges in her public life, particularly regarding her marriage to Charles Ommanney. She attributes the couple's separation to the pressures of reality TV fame. The Daily Mail, quoting Ommanney wrote:

Obviously, my marriage fell apart and so my life has been completely turned upside down and inside out. I've had to do some major soul searching and I still am. Hopefully things will start to improve.

Though she doesn’t regret being on the show she does highlight that it had a significant role to play in her divorce. She explains:

I've met some fantastic people and I really enjoyed working with the crew and the producers and, in general, it's been a good experience.

Catherine and Prince Harry

In several interviews, Catherine Ommanney has spoken about her supposed month-long fling with Prince Harry in 2006. At the time of their encounter, Ommanney was a 34-year-old mother of two, and Prince Harry was just 21. Ommanney, when openly discussing the brief but memorable relationship with the young royal, emphasises the genuine connection and humour they shared during their time together.

If we were to believe Ommanney's recount of their relationship it would show a side of Prince Harry that the public seldom sees — a young man yearning for ordinary life experiences despite his royal status. She describes their interactions as playful and passionate. She even highlights a particular instance where they shared a moment in a bathtub.

We went upstairs to the bathroom and started mucking about like teenagers, singing into toothbrushes like they were microphones.

We got into the bath with our clothes on and one of our friends took a photo on my phone.

According to the woman, the evening continued like this:

We started play fighting and I think we were wrestling on and off for about 15 minutes when I told him I needed to go home.

However, this night filled with fun reportedly wasn’t just a one time thing. Talking to The Sun in November 2022, because she 'does not expect' to be in Spare, Ommanney says:

We continued texting and I saw him again about a week later at a bar in Kensington.

We had another kiss and Harry was very complimentary, telling me how beautiful I was. We met a few more times, always in private bars.

Then, in a not so gentleman move, it appears that the Prince cut ties with the woman. She states that he changed his number and that they didn’t see each other again until 2009 in Barbados when he ‘pushed past his bodyguards to give [her] a kiss and a hug’.

From her interview with The Sun it appears that she regards Prince Harry with affection, describing him as a ‘very brave, charismatic, incredibly funny, intelligent and lovely human being’ and expresses hope for his happiness and fullfilment in his life with Meghan Markle.

His first confirmed relationship with Chelsy Davy

Prince Harry’s long-standing on-off relationship with Chelsy Davy was one of the biggest topics of the 2000’s. According to Tatler, the couple first connected during Prince Harry's gap year in Cape Town. From then, the two dated intermittently from 2004 until finally parting ways in 2011. Their relationship, characterised by its ups and downs, was widely covered by the media, reflecting the intense public interest in the personal lives of the royals.

Chelsy Davy, who has since carved out a niche for herself in the business world with her African jewellery brand, has always been candid about the pressures of being in the limelight during her time with Prince Harry. In a revealing comment about their relationship, Davy reportedly once expressed to friends her decision against royal life.

Express, in June 2021, reported that royal correspondent, Katie Nicholl, heard the words Davy shared with friends. They were quite clear:

There’s no way we are getting married. It’s not a life for me.

However, back in 2011, when Chelsy was Prince Harry’s plus-one for Prince William and Kate Middleton’s wedding, another friend told Nicholl:

[...] it was very significant that she was his plus one for the day.

Harry adores Chelsy and really wants things to work.

According to the article published by Express, Prince Harry considered marrying Chelsy Davy but it was she who wanted to keep things the way they were. The same friend continued to talk to Nicholl and explained:

He has brought up marriage in the past — usually when he’s drunk — but Chelsy's the one to quickly play it all down.

She has watched what Kate has gone through and how much she has had to sacrifice and says it’s not for her.

Talking to the Daily Mail, another source described their on-and-off relationship as ‘very turbulent’ with Chelsy struggling with the attention put on her. This sentiment was echoed by Chelsy herself when she spoke with The Times about the challenges she faced under constant media scrutiny. She explained:

It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn’t cope. I was young, I was trying to be a normal kid and it was horrible.

Despite the eventual breakup, both Harry and Chelsy have maintained a friendly rapport. After their split, Harry spoke about Davy with respect and affection, reflecting on the complexities of their relationship in the glare of the public eye. Their continued amicability was evident when Davy attended Harry's wedding to Meghan Markle in 2018, a gesture that underlined the enduring bond between them, despite their romantic relationship having ended years before.

Moreover though she is glad to be away from the drama the Sussexes are getting, Davy makes sure to not speak about the couple. When, during an interview with Tatler, the journalist prodded her on the topic, she very elegantly said:

I would really rather not say anything about Harry and Meghan.

Chelsy Davy's life post-relationship has been notably less public. She has focused on her business and personal growth, expanding her jewellery brand into a broader lifestyle and travel enterprise. This shift towards a more private and controlled public presence contrasts sharply with the earlier years spent in the unpredictable whirlwind of media attention during her time with Prince Harry.

Caroline Flack, a relationship ruined by the press

Caroline Flack, celebrated for her dynamic presence on Saturday night TV, especially on shows like X Factor and as a triumphant contestant on Strictly Come Dancing, perhaps found her most defining role as the host of Love Island. Taking the reins as the show relaunched in 2015, Flack became a pivotal figure in its transformation into one of the UK's most viewed reality series.

Her journey in the entertainment industry began far from the glittering lights of television studios, in the town of Thetford, Norfolk. After her initial education at Great Hockham Primary and Wayland High School, Flack ventured to London, embarking on her media career in 2002 with a role in Bo' Selecta and subsequently moving into presenting jobs on E4 Music and CBBC.

Flack's career trajectory saw her hosting a variety of prime-time shows, including Gladiators on Sky One and ITV2's spin-off shows for I'm A Celebrity... Get Me Out Of Here! NOW! and The Xtra Factor. Her pairing with Olly Murs on The Xtra Factor led to them co-hosting the main X Factor show in 2015, taking over from Dermot O'Leary.

Despite facing criticism during her stint on the show, Flack's philosophy was to overlook the negativity. She once remarked to The Sun:

Not everyone is going to like you so you have to filter it.

This resilience also shone through in her personal challenges and public scrutiny, particularly highlighted during her brief connection with Prince Harry, which she candidly discussed in her autobiography, Storm In A C Cup.

She wrote:

I knew (Caroline Pinkham) was friends with Prince Harry, and I’d never met him, so I thought, ''Oh that’s quite exciting'', and for a moment I perked up.

So I was just sitting there and he arrived with a few others in tow and we all spent the evening chatting and laughing.

Talking specifically about the media coverage she penned:

I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough.

And so their situationship had to end.

As it is widely known, in 2020, Caroline Flack took her own life after it was announced that she would be charged after allegedly assaulting her partner. At first, Prince Harry didn’t comment on the tragedy or the relationship, but, in 2023, in Spare, he finally addressed it.

Just like Flack herself, he confirmed that the relationship had to end due to ‘press harassment’:

Very soon after [the photographers] papped me and Flack, those photos set off a frenzy. Within hours a mob was camped outside Flack's parents' house, and all her friends' houses, and her grandparents' house.

She was described in one paper as my 'bit of rough', because she once worked in a factory or something. Jesus, I thought, are we really such a country of insufferable snobs?

On the presenter’s death, he wrote:

Caroline Flack, a very good friend of mine, had taken her own life. By the looks of things, she couldn't bear it anymore.

The years of constant harassment by the press had killed her. I felt awful for her family. I can't forget how much she suffered for her fatal sin of going out with me.

Those few lines about Flack didn’t go down well with her former manager who took to Instagram to express his outrage. He called the Prince’s words on his relationship with Flack ‘absolutely gross’.

Beside this publicised moment in time with Prince Harry, Caroline Flack had a lot of success. She showcased her artistic versatility on the West End stage as Roxie Hart in Chicago in 2018, and appeared in The Great Celebrity Bake Off for Stand Up To Cancer. However, her legacy is indelibly tied to Love Island, through which she became a household name. The show's success and her role in it were celebrated by fans and former contestants alike, with many expressing deep sorrow and shock following her untimely death. Molly-Mae Hague, a former contestant, expressed her grief on Instagram:

Caroline you were such a special woman. Your huge smile will stay with me forever... Rest in peace.

This sentiment echoed the collective mourning of a vibrant life cut tragically short.

Ellie Goulding, a very flimsy rumour

Ellie Goulding's love life has been as dynamic and interesting as her music career. In February 2024, she was seen cozying up to surf instructor Armando Perez during a holiday in Costa Rica, possibly indicating a new chapter in her romantic life following her separation from Caspar Jopling.

The British pop star, known for her hit Love Me Like You Do, was photographed engaging in public displays of affection with Perez, who previously taught Shakira to surf. This news comes as Ellie makes her debut as a guest judge on The Masked Singer, stirring interest and bringing her past relationships back into public discussion.

Ellie Goulding has had a star-studded list of ex-partners, including Radio 1 presenter Greg James and the American musician Skrillex, showcasing a pattern of high-profile relationships. Her connections with celebrities like Prince Harry and Ed Sheeran have sparked rumours and songs, such as Sheeran's hit Don't, which is rumoured to be about her. Despite these high-profile connections, Ellie has often found herself clarifying the nature of these relationships, famously denying romantic ties with Sheeran and addressing rumours directly on social media platforms.

In 2016, speculation about a relationship with Prince Harry peaked when Ellie was grilled on live television about potentially expecting his child. Ellie, who is also friends with Princess Eugenie, Harry's cousin, managed to shut down these rumours promptly.

However, at the time Goulding and Prince Harry had been seen together on several occasions including a polo match. Goulding was also present at Prince William and Kate Middleton’s wedding – the now Princess is believed to be a fan of the singer and asked her to perform at the reception.

Finally, the rumours went wild when an anonymous source told The Sun the following:

He [Prince Harry ]has told friends how much he likes Ellie and she is clearly taken by him.

That source ended up being very wrong…

Her personal life, intertwined with her public persona, has always been a point of fascination for fans and media alike. Ellie herself expressed frustration over how female musicians are often defined by the men they date, a sentiment she shared with close friend Taylor Swift.

The one and only Meghan Markle

Her relationship with Prince Harry, punctuated by both romance and controversy, showcases a timeline filled with significant milestones that define her current life. They first met in July 2016, through a mutual friend and quickly connected, leading to back-to-back dates in London and a romantic excursion to Botswana, which Prince Harry described as a pivotal experience confirming Meghan as his ‘soulmate.’

In their Netflix docu-series, Prince Harry recalled how he first spotted Meghan:

I was scrolling through my feed and one of my friends and someone who was a friend had this video of the two of them, like a Snapchat. I was like, 'Who is that?'

The public got their first glimpse into Meghan's life with Harry in late October 2016, when news of their relationship broke, creating a media frenzy that would follow them incessantly. By November 2016, the relationship was officially confirmed by Prince Harry in a rare and personal plea to the press for privacy, highlighting the serious nature of their bond. Their engagement was announced a year later, in November 2017, culminating in a grand wedding at St George's Chapel, Windsor Castle, on May 19, 2018. This union not only signified a new chapter in their lives but also marked a significant cultural moment given Meghan's American and biracial heritage.

Meghan's adjustment to royal life was swift but not without its challenges. She took on royal duties and patronages with vigour but faced relentless scrutiny from British tabloids. The couple's decision to step back as senior members of the Royal Family in January 2020 was a historic move, underpinned by their desire for a more peaceful and independent life, primarily for the wellbeing of their growing family.

Before her marriage to Prince Harry, Meghan was best known for her role as Rachel Zane on the TV series Suits, which she left following her engagement. Her career also included roles in various TV shows and advocacy for gender equality and clean water access through her work with organisations like World Vision.

Moreover, Meghan's personal life before Prince Harry included a brief marriage to film producer Trevor Engelson, from whom she separated in 2013.

This article has been written with the help of A.I

Read more:

⋙ Royal Family: The long history of monarchs who have hidden their health issues

⋙ Prince Harry and Meghan: NYPD has 'sufficient evidence to arrest two individuals' over paparazzi car chase

⋙ Princess Lilibet: The new claims saying Harry and Meghan didn’t have the Queen's authorisation don’t add up

Sources:

Daily Mail: The real story behind Princess Diana's 'revenge' dress - and why it's still so influential 28 years on

The Telegraph: Prince Harry finds it's good to talk with former flame Natalie Pinkham

Harper’s Bazaar: A Look Back At Prince Harry's Dating History

The Sun: Meet F1 presenter Natalie Pinkham, who has worked for Sky Sports for 10 years and Chelsea FC

Daily Mail: Prince Harry's F1 presenter pal Natalie Pinkham weds Owain Walbyoff in Portugal

Daily Star: Ex-Southampton star Jose Fonte's wife is model who had Prince Harry in awe of her boobs

Waterstones – Cassie Sumner: Loving It

Daily Mail: Reality show casualty: D.C. Housewife Cat Ommanney claims show destroyed her marriage

The Sun: Who is Catherine Ommanney and what has she said about Prince Harry?

The Sun: Prince Harry was my toyboy when he was 21 – I was 34 and a mum-of-two and I bet his book doesn’t mention it

Tatler: Inside the world of Chelsy Davy, Prince Harry’s ex-girlfriend, as the court case puts her back in the spotlight

Express: Chelsy Davy’s brutal declaration she would never marry Harry: ‘Not a life for me’

Daily Mail: 'I was Prince Harry's bit of rough': Tragic TV presenter Caroline Flack told how she spent evening 'chatting and laughing' with the Duke when they first met before striking up relationship

Sky News: Caroline Flack: The life and career of Love Island's biggest star

Sky News: Caroline Flack's ex-agent hits out at Prince Harry for repeating 'long forgotten slurs' in memoir

Daily Mail: Inside Ellie Goulding's (very) varied dating history as she's pictured with a hunky surf instructor: Singer, 37, was linked to big music names before marrying art dealer Caspar Jopling - but denied romance rumours with Zac Goldsmith

Express: Masked Singer judge Ellie Goulding's red-faced reaction to Prince Harry romance rumours

The Sun: Who has Meghan Markle dated?

People: Prince Harry and Meghan Markle's Relationship Timeline

Business Insider: Meghan Markle went from a working actress to a royal to a producer for Netflix — here's a complete timeline of her career