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.
Olivia Wilde married a real-life Italian prince
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.
