Prince Harry And Meghan Markle's Most Awkward Celeb Interactions

When Prince Harry and Meghan Markle found that life as working royals was no fairytale, they got help from a celebrity fairy godfather in a land far, far away from the castles and palaces of the U.K. The Duke and Duchess of Sussex even asked filmmaker Tyler Perry to be the actual godfather of their daughter, Princess Lilibet of Sussex.

While Perry didn't turn pumpkins into golden carriages for the couple, in the docuseries "Harry & Meghan," the Sussexes revealed that Perry offered them the use of his Beverly Hills mansion when they had nowhere else to go. Years earlier, Harry had relied on the hospitality of another celebrity during a trip to Hollywood. But in his memoir "Spare," he recalls his experience being more "Alice in Wonderland" than "Cinderella" after he gobbled down some psychedelic mushrooms while staying at the home of "Friends" star Courteney Cox.

By the time he found himself giggling at a talking trash can in Cox's bathroom, hanging out with celebs was old hat to Harry. On "Live with Kelly and Ryan," Spice Girls member Mel B reminisced about Harry and his brother being helpful hosts when her hungry band visited Buckingham Palace in the '90s. She recalled the boys obliging after she asked them, "Can we go in the kitchen and just make some toast and jam?" But while Harry and Meghan have plenty of fond memories of their interactions with celebrities, there are a number of encounters that they'd likely rather forget.

In a March 2023 appearance on "Watch What Happens Live," Aussie actor Rebel Wilson revealed that she had introduced her mom to the Duke and Duchess of Sussex at a polo match in Santa Barbara, California, the prior year. "Met Harry, could not have been nicer," she recalled. "But then, Meghan was not as cool. She wasn't as naturally warm." 

The meeting happened not long after Wilson cracked a joke about the Sussexes while hosting the BAFTA Awards. Before the award for outstanding British film was presented, Wilson suggested that some of the couple's complaints about royal life were pure fiction. "From drama to horror to fantasy, Harry and Meghan's interview with Oprah had it all," she quipped.

However, Wilson's icy reception from Markle may be unrelated to the joke. On "WWHL," the "Bridesmaids" star admitted that her mother wasn't on her best behavior during the introduction. "My mom, being Australian, just asked her all these slightly rude questions," Wilson recalled. "Like, 'Where are your kids?'" Wilson has said that she finds this particular inquiry hurtful herself. In fact, on the "Life Uncut" podcast, she revealed that she considers it mommy-shaming. Just days after Wilson became a mom, she was on the receiving end of it. "I was shocked at the criticism because Chris Hemsworth goes to the gym, [and] people aren't yelling, 'Where's your kids?'" she said. "But why do they do it to every woman?"

According to royal biographer Tom Bower, Prince Harry and Meghan Markle mistakenly believed that Spice Girls member Victoria Beckham had decided to tell the tabloids what they want, what they really, really want to know. As soon as Meghan's relationship with Harry became public knowledge, the British media started using her fresh face to spice up its coverage of the royals. In his book, "Revenge: Meghan, Harry and the War Between the Windsors," Bowers claims that the Sussexes were acutely aware of this and became paranoid that some loose-lipped members of their inner circle were playing ball with the press by leaking information to reporters. "In particular, [Meghan] suspected Victoria Beckham of indiscretion," Bowers writes. "Harry called David Beckham to repeat the accusation. Outraged, Beckham's truthful denials damaged their relationship."

In 2020, a source spoke to The U.S. Sun about the purported incident, claiming that a 2017 report by The Sun raised Meghan's suspicions. The piece in question was an innocuous account of Victoria giving Meghan some recommendations for facialists and salons in London. "It later turned out the leak probably came from a beauty salon," the source said. The insider added that the misunderstanding understandably made relations between the parties involved a bit tense for a while. However, they reportedly patched things up, and when the Beckhams later received an invitation to Harry and Meghan's wedding, they didn't turn it down.

Andy Cohen has had a countess on "Watch What Happens Live," but the Bravo host missed out on the opportunity to gossip about all things housewives with a future duchess. When he appeared on Meghan Markle's "Archetypes" podcast, Cohen learned that Meghan was a "Real Housewives" fan back when she was starring on "Suits." She even tried to get booked on "WWHL" but got turned down. Cohen admitted that this was a big mistake. Huge! "It is now the biggest blunder in the 13 years of the show," he said. 

This came after Cohen had to make another embarrassing confession: He didn't remember meeting Meghan twice before. He gasped when she shared this tidbit of trivia with him. The first time was before "Suits" was even on the air. Meghan recalled approaching him at an event and excitedly chattering away. "I was just gushing," she told Cohen. "And you said, 'Uh huh.'" Throughout their exchange, Cohen was growing increasingly concerned that he'd behaved in a manner that he was about to regret. "Oh god," he said. But Meghan laughed and assured him that he had nothing to worry about. "Now you're here with me, which is amazing," she said. 

Cohen later shared his thoughts about the podcast exchange on "Andy Cohen Live," saying (via Page Six), "It's compelling and awkward." He also said of Meghan's revelation that she attended a "WWHL" taping, "She was gleeful in telling me."

Prince Harry didn't totally creep "Scream" star Neve Campbell out by asking her if she liked scary movies when they met at a party in London, but he did say something to her that left her a bit flummoxed. "We had a little dance, and he told me that he grew up with a poster of me on his wall," she recalled on Dax Shepard's "Armchair Expert" podcast. "I was like, 'Where? In Buckingham Palace?'"

Harry later invited Campbell to a charity event and was apparently eager to chat with her again. She revealed that she brought her partner, British American actor JJ Feild, with her and, naturally, planned to sit beside him. Her royal host, however, had other plans. "Some older gentleman came up to me and told me that I was being seated next to Harry ... He was like, 'He's requested,'" she said. This placed Feild in a somewhat uncomfortable position, but Campbell recalled, "JJ's a Brit, so he was like, 'Okay, whatever. I know how to do this game.'" Instead of arguing with the seating arrangement enforcer, Feild respected Harry's wishes and accepted a different chair elsewhere. Sadly, Campbell didn't spill any details about what she and Harry spoke about. (The most overused horror movie tropes, maybe?)

"Once Upon a Time in Hollywood" star Margot Robbie wasn't star-struck when she encountered Prince Harry at model Suki Waterhouse's house-warming party in 2016. On "The Tonight Show," Robbie shared the story of how she and Harry had a bit of a meet-cute scenario going on when they bumped into each other outside Waterhouse's home: She dropped something, and Harry helped her search for it. At the time, she had no idea that a prince had come to her rescue.

Later on, Robbie hopped in a photo booth with a group that included her good pal Cara Delevingne and Harry, whom she still didn't recognize. When host Jimmy Fallon expressed disbelief over this revelation, Robbie argued that Harry had left his crown at home, making it more difficult to identify him as royalty. He was, however, wearing a pair of glasses that made him look like someone else to the Aussie actor. "I was like, 'Oh my God, I didn't know Ed Sheeran was at the party,'" Robbie recalled saying within earshot of Harry. "And he got really offended. He was like, 'Shut up!'"

But Harry apparently got over being mistaken for the "Castle on the Hill" singer. Robbie later told Extra that she had obtained the Duke of Sussex's phone number, and she even spoke about his response speed when they exchange texts. "He's pretty quick on text actually," she said. "Unlike me — I write back four days later, weeks later sometimes."

When Beyoncé met Meghan Markle and Prince Harry at the U.K. premiere of "The Lion King" in 2019, Queen Bey had already paid tribute to the Duchess of Sussex more than once. Earlier that year, she and Jay-Z filmed their BRIT Awards acceptance speech in front of a painting of Meghan wearing a crown. The Carters later posed for a photo in front of the same painting, and Beyoncé shared it on Instagram along with a message for Meghan. "In honor of Black History Month, we bow down to one of our Melanated Monas," the caption read. "Congrats on your pregnancy!"

In video footage of "The Lion King" premiere, the Sussexes warmly greet the Carters before striking up a conversation with the movie's director, Jon Favreau. "Next time, anyone needs any extra voiceover work, we can make ourselves available," Harry says to the filmmaker. Meghan then quips, "That's really why we're here, to pitch." Part of the exchange is witnessed by Beyoncé, who scratches her nose, laughs, and looks away. 

Some Twitter users believed that Beyoncé's body movements indicated that she was experiencing secondhand embarrassment from watching the Sussexes schmooze, but the "Bow Down" singer wasn't above doing voice work for Disney, and Markle later got her own House of Mouse gig: narrating the nature documentary "Elephant."

When Mickey Guyton's parents joined their daughter at Super Bowl LVI in 2022, they didn't expect to bump into a British prince. They were there to watch Guyton demonstrate her American pride by performing the national anthem, and Guyton wasn't with them when they met Prince Harry and posed for photos with him. The "Black Like Me" singer later told ET, "My mom was like, 'Man, does anyone tell you, you look like Prince Harry?'" The Duke of Sussex attempted to make a dramatic reveal by removing the hat he had on, seemingly believing that this would make it obvious that he was the real deal. But Guyton recalled, "She still didn't get it until I was up in the suite and said that was actually Prince Harry. It was crazy."

Maybe Harry would have been more recognizable if he'd been accompanied by his American wife. But for an undisclosed reason, Meghan Markle stayed at home, and Princess Eugenie joined her cousin at the event.

Guyton got her own photo with Harry, and she made an effort to make him feel like he was back in Merrie Olde England with his family and all of their protocol about the proper way to greet royalty. "I met Prince Harry. He was just lovely. I even curtsied in my track suit," the musician tweeted.

Idris Elba is best know for his work as an accomplished thespian — he played Nelson Mandela in "Mandela: Long Walk to Freedom," became a prestige TV powerhouse with his roles in "Luther" and "The Wire," and showcased his versatility by starring in comic book flicks such as "The Suicide Squad" and "Thor: Love and Thunder." But while Elba is apparently used to getting offered a motley assortment of movie roles, Prince Harry managed to leave him flabbergasted with his once-in-a-lifetime job offer. "He goes, 'Would you DJ at my wedding?'" Elba recalled on "The Ellen DeGeneres Show." "I was like, 'Is this a joke? Are you joking?' And then he's serious." Even if Elba had wanted to say no, how could he turn down such an important royal request?

Elba revealed that he took his job trying to keep the dance floor packed very seriously. "They're good friends and I wanted to make sure they had a great time, so there was a lot of pressure," he said on "The Tonight Show." Harry's request also meant that Elba would have to field endless questions about the 2018 wedding. In 2023, ET Canada wanted to know who could really cut a rug at the reception. "Meghan was the one that was really letting it go," Elba said. "She just had a lot of fun. It was her wedding, so she had the greatest time."

According to Meghan Markle, Ellen DeGeneres convinced her to make a life-altering decision — but the talk show host has no recollection of their encounter. In a 2017 interview with Reader's Digest Best Health, Meghan shared a detailed anecdote about running into DeGeneres and her wife, Portia de Rossi, at an animal shelter. "Ellen goes 'Is that your dog?' And I said, 'No,'" Meghan recalled. "And she's like, 'You have to take that dog.'" Meghan said that DeGeneres even pressured her to think of a name on the spot, which she did: Bogart. "She's like, 'You're taking the dog home,'" said Meghan. As DeGeneres was leaving, she even returned to the window to demand that Meghan adopt the dog one final time. The pressure paid off for Bogart, who got to go home with the future duchess.

The following year, DeGeneres brought up Meghan's story on "The Ellen DeGeneres Show." However, the host told her audience, "I don't remember any of this." Still, she argued that she deserved an invite to Meghan and Harry's wedding for making sure that Meghan became a dog mom, whether she was fully prepared for the role or not. DeGeneres suggested that Meghan would have gone on a downward spiral without the love of a loyal canine companion, eventually losing her job and becoming a criminal with no hope of meeting a prince. "So, I saved her life," DeGeneres quipped.

Members of the royal family are often accused of breaking protocol when they hug members of the public, so Prince Harry is well aware that whether it's appropriate to touch people can be a touchy subject. But when he met Muslim activist Malala Yousafzai during the We Day charity event in 2014, he apparently didn't realize that her religion has strict rules about physical contact. Speaking to Hello!, the event's co-founder recalled, "Prince Harry put his arm around Malala for a photo and very loudly in the corner Malala's mother in Urdu shouts, 'No, no no,' which translated to, 'Not unless you marry her can you touch her.'" This resulted in Harry's face turning the same color as his hair. Yousafzai was also reportedly visibly mortified, and she and Harry took care to avoid any physical contact at all as their photo was taken.

When he and Meghan Markle chatted with Yousafzai on International Day of the Girl in 2020, Harry didn't have to worry about making a similar gaffe — the pandemic forced them to have a virtual conversation. He and Yousafzai had clearly put any awkwardness behind them as they discussed the importance of ensuring that girls have access to education, but Yousafzai did make Meghan laugh by taking a little dig at his sex. "I think it takes boys slightly longer to understand how important education is, but they get there in the end," she said.

There was something holdin' Shawn Mendes back when he got the opportunity to meet Prince Harry and Meghan Markle. The couple never even knew that the singer endured an excessive amount of anxiety at their expense when he performed at Queen Elizabeth II's 92nd birthday bash in 2018. On "The Ellen DeGeneres Show," Mendes described what happened when he spotted the Sussexes at the event. "This is going to be my biggest regret forever. I was walking down the halls, and I see them in one room," he recalled. Mendes believed that striking up a conversation with Meghan would be easy, because he mistakenly thought that Meghan is Canadian like him, possibly because she lived in Toronto while filming "Suits."

But Mendes never got the chance to ask Meghan if she ever gets a hankering for poutine or beaver tails. "I walked in with this confidence, and the second they kind of felt me coming, I just turned around, and my body went numb," he revealed. "I've never been so star-struck like that."

Before he made that awkward exit, Mendes had already survived an even more uncomfortable encounter with the queen. He ended up backstage with Her Majesty, and she did not acknowledge his presence. "You're not allowed to speak to her unless she speaks to you first, so it was like this very 10 minutes of just awkward silence," Mendes recalled. "It was super weird."

In 2016, Prince Harry enlisted Rihanna's help for a noble cause: encouraging people to get tested for HIV. Harry was in RiRi's home country of Barbados when he hastily arranged for the two of them to get tested together for World Aids Day. The goal was to demonstrate how quick and easy the process is. According to the Daily Mail, Harry had discussed the idea with Rihanna just one night prior after meeting her at a concert. 

The prince and the pop princess also toured part of Bridgetown together. They were joined by an HIV counselor, who told them some of the locals' favorite myths about the sex lives of royals. "One of the myths is that royalty don't have sex," he said. Harry tried to steer the conversation in a more SFW direction by asking, "And that royalty has blue blood?" But instead of receiving an answer, he had to stand there with Rihanna and hear a second belief about what doesn't go on in the bedrooms of the British royals. "Another myth is that royalty does not engage in oral sex," their helpful guide informed them.

If Harry blushed then, we're guessing his face was even redder in 2018 when Rihanna shared her expert advice on what he and Meghan Markle should wear on their wedding night. "You could do whatever you want," the Savage x Fenty founder said to ET. "It depends on how savage you wanna be."

What makes a diva? Over-the-top tour rider demands like crystal bowls filled with green M&M's and dressing rooms that must be decorated solely in white? Or the ability to sing sweetly in whistle tones and savagely sling shade? In Mariah Carey's world, it's all about how a woman wears the word. "You think in the grand scheme of things in my life that really matters to me, being called a diva? I am, b***hes, that's right!" she told The Guardian in 2020.

But while the Queen of Christmas is a diva and proud of it, her podcast interview with the Duchess of Sussex took an awkward turn when Carey called Meghan Markle the D-word. "You give us diva moments sometimes, Meghan," the singer told her on "Archetypes." Meghan shared her reaction to Carey's remark with her listeners, saying, "It stopped me in my tracks ... I started to sweat a little bit. I started squirming in my chair in this quiet revolt, like, wait, what? No, what? How? But? How could you? That's not true." Meghan revealed that she revered Carey, and the idea that her idol might view her in a negative light was devastating. Luckily, Carey saved Meghan from a sleepless night by explaining that her idea of a diva is someone who is poised, confident, and stylish. "Yes! I called her a diva, in the most fabulous, gorgeous, and empowering meaning of the word!!!" Carey tweeted.

When you play a member of the royal family on the Netflix series "The Crown" and encounter an actual royal, it has to be somewhat nerve-wracking — especially when that royal is loyal viewer Prince Harry. When he appeared on "The Late Show" in 2023 and revealed that he watches the show, host Stephen Colbert asked him, "Do you fact-check it while you watch it?" Harry replied, "Yes. I do, actually." But on "The Late Late Show," he said that he doesn't mind how the show exercises some artistic license with the lives of his family members, revealing that it still manages to capture the essence of royal life. He also took a dig at the tabloids, saying, "I am way more comfortable with 'The Crown' than I am seeing the stories written about my family or my wife or myself." 

Harry is so cool with the show, in fact, that he had a little fun with one of its stars. "House of the Dragon" actor Matt Smith played Harry's late grandfather, Prince Philip, on the series, and he learned about Harry's viewership in an unforgettable way. "I met Harry once, at polo, which sounds a bit grand, but it wasn't that grand," Smith said during a "Today" interview. "And he walked up to me and went, 'Granddad.'" Smith also revealed that a friend of his once asked Philip if he watched the show. His response? "Don't be ridiculous!" 

As Timon and Pumbaa, comedians Billy Eichner and Seth Rogen got to be besties with royalty in "The Lion King." But they learned that properly greeting Prince Harry and Meghan Markle wasn't as simple as offering them a rotten log teeming with tasty bugs. On "Jimmy Kimmel Live!," Eichner revealed that preparing to meet the Sussexes at the London premiere of "The Lion King" was a bit like studying for a stressful test. "What makes you nervous, in the days leading up to it, they email you a protocol of how you're supposed to greet Prince Harry and Meghan, and they're very intense about it," Eichner said. He revealed that the royal rules were even giving his co-star Beyoncé the jitters.

Eichner and Rogen also questioned what would happen if they didn't follow protocol when meeting the Sussexes. "I assume you get put in the Tower Of London if it all goes wrong," Rogen quipped on "This Morning." 

The Daily Mail shared a video of a visibly nervous Eichner preparing to meet the royals on the red carpet and saying to Rogen, "I'm going to say pleasure to meet you ... is that bad? I'm going to say it. I'm going to say it." On Twitter, he confirmed that this is the greeting he went with — and he wasn't shackled, hauled off, and thrown in a cell. He said of the Sussexes, "They were both super down to earth and lovely."