There are some royal romances that everybody knows about, like Prince William and Kate Middleton.
Their 2011 marriage remains one of the biggest cultural moments of the past decade. But there are some dalliances and trysts that have somehow slipped under the radar.
From rumoured flings between Oscar-winning icons and European princes to the unlikely royal connections to enduring marriages and relationships, let's take a look at the star-crossed courtships of showbiz royalty and real royalty over the years.
The celebrities who have reportedly dated royalty
Naomi Campbell and Prince Albert
For the record, neither supermodel Naomi Campbell nor Monaco's Prince Albert II have ever confirmed their rumoured relationship, but a simple Google search will show a horde of images of the two being flirty and playful.
Whether it was serious or not, the pair remained on friendly terms as Naomi was invited to Prince Albert's wedding to Charlene Wittstock in 2011.
Olivia Wilde married a real-life Italian prince
Actress and director Olivia Wilde has been romantically linked to some impressive men, including actor Jason Sudeikis and singer Harry Styles. But the real jewel in the metaphorical crown was real-life European nobility.
The Don't Worry Darling filmmaker was married to photographer and musician Tao Ruspoli between 2003 and 2011. Tao is the son of Italian aristocrat Alessandro Ruspoli, 9th Prince of Cerveteri.
Cressida Bonas and Prince Harry
Before he found his happily-ever-after with Meghan Markle, Prince Harry dated model and actress Cressida Bonas for around two years.
The pair were a popular fixture in the British tabloids, and Cressida is thought to remain on good terms with the royals. She was even invited to the royal wedding of Harry and Meghan in 2018.
Caroline Flack and Prince Harry
The late TV presenter Caroline Flack - known for hosting the likes of Love Island before sadly passing away in 2020 - enjoyed a casual courtship with Prince Harry in the late 2000s.
Prince Harry himself confirmed this in his memoir, Spare, calling her "funny and loving" and mentioning going on several dates before deciding to end the relationship due to the intense media scrutiny.
In the book, he writes, "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?"
Jessica Chastain
Some people just have it all, don't they? From her Oscar winning film career to her stunning red carpet looks, Jessica Chastain is modern Hollywood royalty. And, as it turns out, she can claim actual nobility status thanks to her marriage to Gian Luca de Preposulo.
Marrying in 2017, Gina Luca is part of the Passi de Preposulo family which dates back to 973. Gian Luca’s father is Count Alberto Passi de Preposulo, who still owns the family’s lavish and regal estate, the seventeenth-century Villa Tiepolo Passi.
Gwyneth Paltrow was rumoured to have dated a future king
Gwyneth Paltrow is a Hollywood icon - and the queen of wellness. But, if rumours are to be believed, there was the potential the Goop legend of getting herself a real crown.
In 2002, the same year Gwyneth would eventually meet her one-time husband, Chris Martin, she was also linked to the now King Felipe of Spain. He was just - 'just' - a prince at the time, and the pair have never confirmed the rumours, but speculation was rife.
Ellie Goulding was linked to Prince Harry
There were widely reported rumours of a burgeoning romance between singer Ellie Goulding and Prince Harry between 2015 and 2016.
The pair were never officially confirmed as a couple, but Ellie was known to be in the inner circle with the royals, performing at Harry's 30th birthday and appearing in the closing ceremonies of the 2014 Invictus Games.
Ellie also performed at the reception for Prince William and Kate Middleton's 2011 wedding.
Chelsy Davy and Prince Harry
Before Prince Harry settled down with Meghan Markle and started his happy family, his longest girlfriend was Chelsy Davy, a Zimbabwean businesswoman.
The two dated for around seven years, and first got together during Harry's gap year in Cape Town. Chelsy was Harry's date to the iconic 2011 royal wedding of Prince William and Kate Middleton, but the pair would break up later that same year.
Chelsy remains close with the royals, though, and was a guest at Princess Eugenie's 2018 wedding to Jack Brooksbank.
Mollie King and Prince Harry
A King and a prince... talk about a royal romance.
The Saturdays singer and Radio 1 host Mollie King confirmed that she had a brief romance with Prince Harry back in 2012, shortly after Harry had called it quits with his long-term girlfriend, Chelsy Davy.
Rob Lowe
One of the original Brat Pack stars of the 80s, Rob Lowe was a bona fide heartthrob. And his charming ways even worked on royalty.
According to his autobiography, Stories I Only Tell My Friends, the St Elmo's Fire actor recounted his whirlwind romance with Princess Stephanie of Monaco. The passionate romance moved quickly, he claimed, writing that he moved into Stephanie’s Paris apartment the day after they first met in 1986.
Jamie Lee Curtis
Jamie Lee Curtis is Hollywood royalty, with her parents being screen legends Tony Curtis and Janet Leigh. However, thanks to her enduring marriage to actor and writer Christopher Guest, she can lay claim to true aristocratic status.
Christopher - who married Oscar-winning Jamie Lee in 1984 - officially inherited his father's title of Baron Haden-Guest in 1986, meaning Jamie can technically refer to herself as Baroness Haden-Guest.
Zsa Zsa Gabor
We're including this one because it's one of those stranger-than-fiction stories that prove the Golden Age of Hollywood had some truly unique characters.
When is a royal title not really, well, real? When some chancer pays for it.
That's right, Zsa Zsa Gabor's ninth husband might have seemed like one of the most impressive in her roster, but he actually paid for his royal title. Frédéric Prinz von Anhalt (also known as Prince Frédéric of Anhalt, Duke of Saxony and Westphalia, Count of Ascania) landed his royal title by paying cash-strapped Princess Marie Auguste of Anhalt to adopt him as an adult.
Janice Dickinson
Janice Dickinson - sometimes referred to as the original supermodel and known for her outspoken antics on the likes of America's Next Top Model - is alleged to have enjoyed a brief dalliance with Prince Albert II of Monaco.
The supermodel briefly alludes to her trysts with Grace Kelly's son in her 2006 book Everything About Me is Fake...and I'm Perfect.
Diane von Furstenberg
Diane von Furstenberg has packed many different lives into her time on earth, from becoming a fashion legend with her eponymous label and the iconic wrap dress to being actual nobility.
The celebrated designer and entrepreneur was known as Her Serene Highness Princess Diane of Fürstenberg during her marriage to Prince Egon of the German noble house of Fürstenberg from 1969 to 1983.
Kit Harington and Rose Leslie – the acting couple who both have royal ties
Kit Harington and Rose Leslie feel like a perfect match - both actors, and both with noble ties, the couple have reportedly been dating since around 2012, and were married in 2018.
The Good Fight actress Rose Leslie is the daughter of Aberdeenshire Chieftain of Clan Leslie and grew up in an actual castle. Her Game of Thrones co-star - and husband - Kit's grandmother, Lavender Cecilia Denny, married Richard Harington, the 12th Baronet Harington, a distant but direct descendant of King Charles II.
Lee Radziwill almost one-upped her famous sister, Jackie Kennedy
Most people know of Jackie Kennedy Onassis. Chic, glamorous and resilient. But, for some, her sister, Lee Radziwill, was the true 'It Girl' of their family.
A muse to fashion designers like Giorgio Armani and friends with icons including Truman Capote, Lee was one of the defining socialites of her time. And, while Jackie married a president, Lee bagged a prince.
Lee's second husband was Polish prince Stanislaw Albrecht Radziwill.
Claudia Schiffer was linked to Prince Albert II
While never confirmed, there were plenty of reports that supermodel Claudia Schiffer and Prince Albert II of Monaco dated in the early 1990s.
Albert has gone on record dismissing the "hoopla" around the rumours, but never outright denied it. And speaking to Vanity Fair in 1993, Claudia sidestepped the question, simply replying: "I prefer not to talk about that... I do know Albert very well. I live in Monte Carlo, so it's only normal."
Brooke Shields and Prince Albert
In 1979, Brooke Shields and Albert II of Monaco found themselves in the eye of a media storm after dating rumours exploded in the press.
A flirtatious appearance at a tennis match between the two was the cause of the speculation, but the two parties have never confirmed or denied the rumours.
Luann de Lesseps - reality TV royalty with real aristocratic links
Reality TV lovers will be familiar with the long-serving Real Housewives of New York alum who built an entire persona around her connection to aristocracy.
Luann – a nurse originally from Connecticut – married French Count Alexandre de Lesseps in 1993. She would refer to herself often as Countess Luann and launched a pop career under that name.
Sonja Morgan
A reality TV star who has been vocal about connections with royalty and aristocracy, Sonja Morgan is a Real Housewives of New York veteran. She starred on the hit series for 11 seasons, and, while she took her last name from an impressive American dynasty, marrying John Adams Morgan (of the JP Morgan financial dynasty), she also has mentioned flings with royals.
On (and off) the show, Sonja made reference to dates with Monaco’s Prince Albert II. On one episode, she told Bethenny Frankel, "I used to wear this with Prince Albert when we were dating in Monaco. Can you believe this? It has a skirt. I must have left the skirt at Albert's."
James Gilbey, and Princess Diana’s ‘Squidgygate’
James Gilbey was the heir to Gilbey's Gin, and found himself in a media storm after calls between him and Princess Diana were leaked.
British intelligence allegedly recorded Diana and her alleged lover in several phone calls, in which Gilbey said "I love you" and referred to Diana as "Squidgy” at least 53 times.
The tapes were sold to The Sun and later published in The National Enquirer in the U.S. in 1992, the same year Diana and Charles separated before finalising their divorce in 1996.
Sophie Winkleman
A royal romance that is still going strong, British actress Sophie Winkleman - sister of The Traitors presenter Claudia Winkleman and known for playing Big Suze in the cult classic, Peep Show - pivoted from a successful acting career to embracing her royal role after becoming Lady Frederick Windsor when she married the son of Prince Michael of Kent, first cousin of Queen Elizabeth II in 2009.
Rita Hayworth
Screen legend Rita Hayworth was known for her high-profile marriages, including one to director Orson Welles.
She swapped Hollywood royalty for actual royalty in 1949 when she married Prince Aly Khan, the son of Sultan Muhammed Shah. So, Grace Kelly and Meghan Markle aren't the only actresses to get a taste of real-life royal romances.
The Gilda star and her prince split bitterly after a row erupted over how to raise their daughter, and Rita fled to Lake Tahoe.
Emma Thynn's aristocratic romance made history
Emma Thynn was a model, socialite and fashion editor before meeting Ceawlin Thynn, the Viscount Weymouth. Their relationship survived a lot, including alleged feuding with Ceawlin’s parents, who were disinvited from their 2013 wedding. A royal courtship with a happy ending, the couple remain happily married with two children. In 2020, she officially became the first Black marchioness in British history, and the couple act as the chatelaines of Britain’s historic Longleat Estate, including the Longleat House and safari park.
Barron Hilton II - American dynasties meet European nobility
Perhaps better known as the younger brother of Paris Hilton, Barron Hilton II's marriage helped connect the American Hilton dynasty to a European clan who have a connection to King Charles III.
Paris' younger brother married Tessa Gräfin von Walderdorff, a member of the German noble Walderdorff family and a descendant of the German House of Löwenstein-Wertheim-Rosenberg.
Through her father, Count Franz, Tessa is related to King Charles III and the British royal family, sharing mutual ancestry from Francis, Duke of Saxe-Coburg-Saalfeld and his second wife, Countess Augusta Reuss of Ebersdorf.
Gene Tierney - another Hollywood icon who charmed a prince
A striking beauty and accomplished actress, known for such classics as Laura and The Ghost and Mrs Muir, Gene Tierney briefly dated royalty.
Prince Aly Khan was still legally married to screen siren Rita Hayworth when he reportedly proposed marriage to Gene. His father, Aga Khan III, reportedly railed against his son's playboy ways, condemning another public relationship, and Gene and Aly ultimately split after a year-long engagement.
Princess Margaret and Warren Beatty
Madonna. Joan Collins. Natalie Wood. Cher. Warren Beatty's list of rumoured and confirmed romances basically read like a who's who of the entertainment world, but, if a report from 1975 is to be believed, he also expanded his pool to royalty.
A 1975 mention in Playgirl included Princess Margaret on a list of women Warren Beatty had been connected with - is it true? We don't know. Warren has never confirmed or denied the list and has been married to actress Annette Bening since 1992.
Roddy Llewellyn’s (in)famous affair with Princess Margaret
Being splashed all across the papers in a pair of Union Jack swimming trunks might seem far too undignified for anyone associated with royalty, but it was the pictures of Roddy Llewellyn relaxing at Mustique with Princess Margaret that seemingly confirmed the worst-kept secret of the pair's romance.
Margaret was married to Antony Armstrong-Jones when the pictures leaked, but their marriage was reportedly on the rocks long before. Her relationship with Roddy Llewellyn, a landscape gardener and aristocrat, is thought to have started around 1973.
At the time, Margaret was 43 and Roddy was 25. The affair was fictionalised in season three of Netflix's The Crown.
Eddie Fisher and Princess Margaret
Eddie Fisher is arguably best remembered for his romantic life rather than his career as a singer. He was famously the man who cheated on America's Sweetheart, Debbie Reynolds, leaving her for her best friend, Elizabeth Taylor.
Eddie and Elizabeth married - her fourth - for five years after the scandalous affair.
But, as it turns out, there might have been another noteworthy fling for the singer. According to Terry Richard, who was Eddie Fisher's fourth wife, the crooner and Princess Margaret had a steamy one-night affair in 1953.
Terry opened up about the alleged tryst to the Daily Mail in 2023 while promoting her memoir, Beauty Queen Dreams.
Lady Victoria Hervey and Prince Andrew
Model and socialite Lady Victoria Hervey is the daughter of the 6th Marquess of Bristol, half-sister of the 7th Marquess, and sister of the 8th Marquess and Lady Isabella Hervey.
With such aristocratic connections, it's no surprise she has had a tryst with royalty. She briefly dated Prince Andrew in 1999, and has been a rare voice of public support for the disgraced Duke of York in recent years.
Laura Harring
Laura Harring is best known for her critically acclaimed performance in the atmospheric classic film Mulholland Drive.
The actress - also a former Miss USA - became Countess von Bismarck-Schönhausen when she married Count Carl-Eduard von Bismarck-Schönhausen, the great-great-grandson of German chancellor Otto von Bismarck, in 1987.
The marriage ended two years later, reportedly as Laura wanted to continue pursuing acting opportunities despite her new noble status.
Sofia Kristina Hellqvist, from reality to royalty
Never let it be said that reality TV can't open many, many doors. Despite a somewhat negative connotation amongst some circles, the Swedish royal family proved themselves to be far from snobbish towards the genre, embracing a former glamour model and reality TV star into the fold.
Before she married Sweden’s Prince Carl Philip in 2015, Princess Sofia was known for starring in the 2000s reality show Paradise Hotel alongside adult film star Jenna Jameson.
