When a celebrity dates another celebrity, we become doubly invested in their relationship. It often leads us to creating a nickname for the couple, dissecting their body language at every event and wondering if and when they’re going to tie the knot. Having a couple with two A-list celebrities might seem like the ultimate in famous people #couplegoals, but there are times when it can be topped. One of those occasions is when celebrities look beyond the Hollywood dating pool and hook up with royalty.
Celebrities often date other famous people while royals often date people with blue blood, castles and titles that are as impressive as their own. But, there are those special occasions where Hollywood and real-life princes and princesses come together and we have new couples to obsess over. The relationships might not always last, but we’ll still remember them because they often seem like something out of a storybook.
17. Grace Kelly
Grace Kelly might actually have the biggest fairy tale romance of them all. She was a darling of Hollywood in the 1950s starring in movies like High Noon, Rear Window, To Catch a Thief and The Swan — in which she actually played a princess. Her last film was High Society in 1956. She then reired from acting at only 26 to marry Prince Rainier III of Monaco. The two met for the first time at the Cannes Film Festival in April 1955 when they had a photo shoot together. Hearing about it now, it probably sounds familiar to another actress’s story, right? More on her later.
16. A.J. Langer
You might not recognize the name A.J. Langer, but she appeared on My So-Called Life. Perhaps you better know her as Allison Joy Courtenay, Countess of Devon or her newest title from 2015 The Right Honourable The Countess of Devon. The actress received the titles when she traded Hollywood for England and married Charles Courtenay, 19th Earl of Devon in 2005.
15. Jenna Coleman
Jenna Coleman was already known for acting (and leaving) Doctor Who when rumors swirled in 2015 that she and Prince Harry were dating after some photos of them “looking flirty” surfaced, aka he had his hand on her leg. Nothing really happened, at least publicly, so we’ll let you decide whether it was just a fling or just some flirting.
14. Zsa Zsa Gabor
Zsa Zsa Gabor was a former Miss Hungary and actress who appeared in films from the 1950s to 1990s. She was known for grace and charm as well as for being married nine times. Her last marriage happened in 1986 to Frédéric Prinz von Anhalt. He actually wasn’t born in royal blood. At the age of 36, he paid Princess Marie-Auguste of Anhalt to adopt him. (Just go with it.) He doesn’t have any royal claims and the “prinz” in his name is nothing more than his last name, but the fact he has styled himself as a prince has made many think he actually is one. So, he and Zsa Zsa make it onto the list.
13. Sofia Kristina Hellqvist
If you’re up on your royal knowledge from around the world, you probably know about Sofia Kristina Hellqvist. She was a glamour model and reality TV star before she married the dashing Prince Carl Philip of Sweden in 2015. She posed in semi-nude photos and kissed adult film star Jenna Jameson while filming a reality TV show, but thing weren’t *scandalous* enough to get in the way of the couple’s relationship. Their romance was confirmed in 2010 and their engagement was announced in 2014. She is now known as Princess Sofia, Duchess of Värmland.
12. Jamie Lee Curtis
Jamie Lee Curtis has a number of interesting connections in her family. For one thing, she’s Hollywood royalty as the daughter of actress Janet Leigh and actor Tony Curtis. That’s just the start. She married Christopher Guest in 1984, which means her name is technically Jamie Lee Haden-Guest, Baroness Haden-Guest. Guest is known as a director, musician and actor, but he’s also Christopher Haden-Guest, 5th Baron Haden-Guest.
11. Naomi Campbell
Actors dating models is nothing new, but royals dating models? That’s interesting. Albert II of Monaco had a history of dating gorgeous models in the 1990s and 2000s. The list includes supermodel Naomi Campbell and there are a number of PDA-filled photos to prove they dated. It seemed like there were no hard feelings because Naomi was still invited to the Monaco royal wedding in 2011 when Albert wed former Olympian Charlene Wittstock. It’s also interesting to note he dated celebrities, just like his father Rainier III, Prince of Monaco.
10. Ellie Goulding
You’ve probably heard that Prince Harry and Ellie Goulding are good friends. The singer even performed at Prince William and Kate Middleton‘s wedding! But there have been reports that there was more to their relationship than strictly friendship with “the pair spotted canoodling at the Audi Polo Challenge in May 2016” and sending flirty messages. She did get an invitation to Prince Harry and Meghan Markle’s wedding, though, which means she was the third ex of Harry’s to attend the event.
9. Olivia Wilde
Olivia Wilde and Jason Sudeikis are the definition of adorable and hilarious relationship goals. Prior to them getting together, however, the actress was married to Tao Ruspoli from 2003 to 2011. If the name doesn’t ring a bell, he’s part of the aristocratic Ruspoli family who own the ancestral residence Castello Ruspoli. He’s a musician, filmmaker and son of Alessandro Ruspoli, 9th Prince of Cerveteri.
8. Diane von Fürstenberg
You probably know the name and clothes of Diane von Fürstenberg, but do you know the full story of her life? She’s actually a former princess. Let us explain: She was actually born Diane Simone Michelle Halfin in Brussels. When she married Prince Egon von Fürstenberg of Germany in 1969, she became Princess Diane von Fürstenberg. Following their separation in 1972 and eventual divorce in 1983, she lost the princess title but kept the surname. It was in 1974 that Diane created her iconic wrap dress so who knows what would have happened if she remained married to the prince.
7. Rita Hayworth
You probably know all about Grace Kelly and Prince Rainier III, but did you know actress Rita Hayworth also dated a royal? In fact, she actually married one. After appearing in films like Gilda, The Lady From Shanghai and The Loves of Carmen — and getting married a few times — she met Prince Aly Khan, son of Sultan Mahommed Shah, Aga Khan III, at the Cannes film festival in 1948. (Sound familiar?) They had a year courtship, despite her still technically being married to Orson Welles, before she broke her contract with Columbia Pictures to get married in 1949. Prince Aly and Rita had a daughter together, Princess Yasmin Aga Khan, but divorced in 1953. Despite the divorce, she was actually one of the first actresses to become a princess proper.
6. Cressida Bonas
We’ll admit that Cressida Bonas was known first as Prince Harry’s girlfriend and as an actress second. Her star might not have been as bright as others when they began dating royals, but she was still a celebrity when she dated Prince Harry between 2012 and 2014. She made her debut on screen in 2009 with a small role in Trinity. In 2014, she made her theatrical debut with There’s a Monster in the Lake. She and Harry parted ways and she has continued to gain acting and modeling work.
5. Rob Lowe
Rob Lowe has admitted that he had a fling in the 1980s with Princess Stéphanie of Monaco, the singer-model daughter of Grace Kelly and Prince Rainier III. The actor was already beginning to establish himself with a Golden Globe Award nomination for Best Supporting Actor in a Series, Miniseries, or TV Film for his role in Thursday’s Child in 1983. Who’s to say what would have happened if his relationship with the princess was more than a short term thing?
4. Claudia Schiffer
Claudia Schiffer is another supermodel who dated Prince Albert II of Monaco. There were reports of the pair dating in the early 1990s, although they denied it at the time. Remember that the ’90s were when supermodels were at the height of their fame, so you can imagine what a big couple a famous model and a prince were…
3. Jessica Chastain
Perhaps we should be calling Jessica Chastian a royal title because she married Gian Luca Passi de Preposulo in June 2017 after a number of years of dating. Gian is a member of the Passi de Preposulo Italian noble family who own the Villa Tiepolo Passi and have a long lineage. You probably don’t need us to explain Jessica’s acting credits to you. She has been racking up movie credits and award nominations for a good part of the 2010s.
2. Gwyneth Paltrow
Prince Albert II of Monaco didn’t just date supermodels. Sure, he adhered to his reputation of dating beautiful women, but he switched things up a bit by dating actresses along with models. Gwyneth Paltrow was apparently one of the actresses he dated during his playboy days of the 1990s and early 2000s. Gwyneth also holds a record for dating two royals. She was also linked with then-Prince Felipe VI of Spain in 2002. He married Letizia of Spain in 2004 who was a journalist. She is now Queen of Spain and he is now King of Spain. As for Gwyneth, she’s engaged to Brad Falchuk.
1. Meghan Markle
We probably don’t need to explain this one because we all know you watched countless Meghan Markle biography specials before her royal wedding to Prince Harry. But we will explain it again. Meghan had a few Hollywood jobs before marrying Harry and her most memorable acting work was her role on USA’s Suits. She started her relationship with Prince Harry in 2016 and they announced their engagement in late 2017. Now that they’re married, she’s officially Meghan, Duchess of Sussex.