Over the years, the small circle of Hollywood has crossed over with the small circle of royalty and romance has bloomed.
The combination of celebrities and royals—which has occurred more times than you think—has lead to some very successful marriages (see Meghan Markle and Grace Kelly’s run-in with princes) and some very fun flash-in-the-pan flings (refer to Gwyneth Paltrow’s reported romance with the future King of Spain and Rob Lowe’s affair with Princess Stéphanie of Monaco).
But whether the relationships ended in wedded bliss or not, they’re still fun to reflect on.
Below, 27 star-crossed lovers.
Gwyneth Paltrow and Prince Felipe of Spain
Could Gwyneth Paltrow have been the Queen of Spain? Rumours swirled in 2002 that Paltrow may have been seeing Prince Felipe, but nothing was ever confirmed. Prince Felipe, now King Felipe VI, is now married to Queen Letizia.
Rose Leslie and Kit Harington
In Game of Thrones, Harington played the royal and Leslie played the commoner. But, in reality, it’s the other way around. Rose Leslie was born Rose Eleanor Arbuthnot-Leslie, the daughter of the Aberdeenshire Chieftain of Clan Leslie. She was raised at Lickleyhead Castle until she was 10.
Rob Lowe and Princess Stéphanie of Monaco
According to the tabloids at the time rebellious Princess Stéphanie of Monaco had a shortlived affair with actor Rob Lowe.
Elmaleh and Charlotte Casiraghi,
Elmaleh, a French-Moroccan stand-up comedian and actor, dated and had a child with the glamorous Charlotte Casiraghi, Princess Caroline of Monaco’s daughter.
Ellie Goulding and Prince Harry
They’re both happily married now, but rumour has it that Prince Harry had a short-lived fling with singer Ellie Goulding in 2016.
Meghan Markle and Prince Harry
Perhaps the most famous ‘celebrity dating a royal’ story yet, American actress Meghan Markle not only dated a royal but married one! She is currently married to Prince Harry and now goes by ‘Meghan, Duchess of Sussex.’
Claudia Schiffer and Albert II, Prince of Monaco
During his youth, Prince Albert was rumoured to have dated supermodel Claudia Schiffer.
Naomi Campbell and Albert II, Prince of Monaco
Naomi Campbell was another supermodel Prince Albert was linked to, back in the day.
Caroline Flack and Prince Harry
British host Caroline Flack has two famous Harrys in her (rumoured) dating history: Harry Styles and Prince Harry. The two dated in 2009 but soon called it off due to the press attention.
Flack wrote in her book, “To meet a prince is so unlikely, it would be weird not to acknowledge it. However, 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.”
Emma McQuiston and Ceawlin Thynn, Viscount Weymouth
Model Emma McQuiston is a host, socialite and Strictly Come Dancing contestant. She met and married Ceawlin Thynn, Viscount Weymouth, becoming Emma Thynn, Viscountess Weymouth.
Zsa Zsa Gabor and Frédéric Prinz von Anhalt
One of Zsa Zsa Gabor’s nine marriages was to Frédéric Prinz von Anhalt, which technically made her royalty. However, her husband’s ‘royal status’ was cause of much dispute as—rumour has it—he paid the elderly Princess Marie-Auguste of Anhalt (to who he had no biological relation) to adopt him at the age of 36. He and Gabor then adopted more than 10 males to give them the ‘prince’ title—allegedly to the tune of $2,000,000 USD each.
Jamie Lee Curtis and Christopher Guest
Jamie Lee Curtis’ husband, Christopher Guest, is actually the 5th Baron Haden-Guest, making Curtis “The Right Honourable The Lady Haden-Guest”. However, Curtis chooses not to use her title and has been quoted as saying, “It has nothing to do with me”.
Jessica Chastain and Gian Luca Passi de Preposulo
Not many people know that Jessica Chastain’s now-husband, Gian Luca Passi de Preposulo, is “an Italian count of the Passi de Preposulo noble family.” They married at his family’s historic estate in Italy.
Diane von Fürstenberg and Prince Edouard Egon Fürstenberg
Not many know that Diane von Fürstenberg, born Diane Halfin, got her famous last name via her first husband, a German prince. The designer met Prince Egon von Fürstenberg in university and, upon their marriage, became ‘Her Serene Highness Princess Diane of Fürstenberg.’
Charlene Wittstock and Albert II, Prince of Monaco
Olympic swimmer Charlene Wittstock was already a name in her native South Africa before meeting and marrying Albert of Monaco. They now share two children.
Rita Hayworth and Prince Aly Khan
Actress Rita Hayworth’s third husband was Prince Aly Khan, son of son of Sultan Mahommed Shah, Aga Khan III. They had one child, a daughter named Princess Yasmin Aga Khan, and were divorced in 1953.
Sofia Hellqvist and Prince Carl Philip of Sweden
Former model and reality TV contestant Sofia Hellqvist met and married Sweden’s Prince Carl Philip, making her ‘Her Royal Highness Princess Sofia of Sweden, Duchess of Värmland.’
Tatiana Blatnik and Prince Nikolaos of Greece and Denmark
Tatiana Blatnik worked as a event planner and in PR before marrying Prince Nikolaos of Greece and Denmark.
Lee Radziwill
While her sister, Jackie, became First Lady when she married President John F. Kennedy, Lee Radziwill (née Bouvier) became royalty when she married Prince Stanisław Albrecht Radziwill, becoming ‘Her Serene Highness Princess Caroline Radziwill’.
Zara Phillips and Mike Tindall
Princess Anne’s daughter, Zara, met and married English rugby player Mike Tindall in 2010. They now share two children, daughters Mia and Lena.
Grace Kelly and Rainier III, Prince of Monaco
One of the most famous instances of a celebrity dating (or, rather, marrying) a royal, American actress Grace Kelly married Rainier III, Prince of Monaco, in a lavish ceremony in 1956. She is considered one of the most famous and beloved royals ever.
Cressida Bonas and Prince Harry
Bonas, a socialite, actress, model and It-girl, dated Prince Harry between 2012 and 2014.
Kendra Spears and Prince Rahim Aga Khan
Kendra Spears worked for many years as a successful model, appearing on the covers of several high-profile magazines and in campaigns for Prada, Calvin Klein, Armani, Moschino and Etro. In 2013, she married Prince Rahim Aga Khan, son of Aga Khan IV, and was henceforth known as Princess Salwa.
Sophie Winkleman and Lord Frederick Windsor
English actress Sophie Winkleman appeared in Two and a Half Men, CSI: Miami and Red Dwarf before meeting and marrying Lord Frederick Windsor, the son of Prince Michael of Kent.
Olivia Wilde and Tao Ruspoli
Although now happily married to Jason Sudekis, Olivia Wilde was married to Prince Tao Ruspoli, from the aristocratic Ruspoli family, for eight years.
Wallis Simpson and Prince Edward, Duke of Windsor
Wallis Simpson was an American socialite who fell in love with King Edward VIII, leading him to abdicate his throne. They later married and lived separately to the royal family.
Casper Van Dien and Catherine Oxenberg
Starship Troopers and Beverly Hills, 90210 star Casper Van Dien was married to fellow actress Catherine Oxenberg, who happened to be the daughter of Princess Elizabeth of Yugoslavia.
Laura Harring and Count Carl-Eduard von Bismarck-Schönhausen
Former Miss USA and Mulholland Drive star was married to Count Carl-Eduard von Bismarck-Schönhausen in 1987. Despite divorcing, she is still known as Countess von Bismarck-Schönhausen.
