15 of the Royals' Most Controversial Relationships

Martha Sorren | Jun 24, 2020 Celebrities
15 of the Royals' Most Controversial Relationships
Image: George Pimentel/WireImage

Meghan Markle and Jessica Mulroney
George Pimentel/WireImage

We're all judged by the company we keep, but none more so than famous people -- especially the royal family. As the figureheads of the UK and many commonwealth countries, it's their duty to be upstanding citizens. But sometimes, their associates don't have the same degree of good behavior. Over the years, some of the royal family's friendships and relationships have been quite scandalous in nature, and new outrageous situations happen all the time.

Sometimes, it's not the fault of the royal that his or her family member -- or friend -- goes off and does or says something stupid or illegal, putting the whole monarchy in hot water. Other times, the royals should probably have known better before fraternizing with certain people.

Inappropriate friendships and relationships aren't new to the royals. For centuries, they've had illicit romances and ties to dictators and other seedy people. Some members of the royal family even associated with Hitler and the Nazis. Compared to that, some of these scandals may pale in comparison, but they all brought negative attention to the monarchy.

In recent years, standards have changed, and things that used to be widely accepted about royals are no longer OK. Kings used to have tons of mistresses, and though adultery has still plagued the monarchy to this day, it's now the kind of situation that reflects badly on the crown. And as technology and media get better, people are more easily caught doing things they shouldn't or associating with people they shouldn't. That's led to more scandal in recent years. 

Here are 15 friendships and relationships that the royals could have done without.

  • Prince Andrew Was Friendly With a Convicted Sex Offender

    Prince Andrew
    Splash News

    Prince Andrew's friendship with the late Jeffrey Epstein goes back decades, and the two remained close even after Jeffrey Epstein was convicted of soliciting a minor for prostitution. In late 2019, Prince Andrew did an interview with the BBC to justify/apologize for the friendship, and people weren't pleased with what he had to say. Eventually, the whole scandal led to Prince Andrew stepping back from his royal duties.

  • Prince Andrew Was Tied to a Shady Businessman

    Prince Andrew
    Splash News

    Jeffrey Epstein wasn't Andrew's only scandalous friendship. According to The Guardian, the prince once had ties to businessman Tarek Kaituni who has been convicted of drug possession and gun smuggling. The outlet reported that the two were close enough for Tarek to be invited to Andrew's daughter Princess Beatrice's 21st birthday party, and that she was gifted a diamond necklace by the businessman. 

  • Meghan Markle's Friend Is in Hot Water for Racist Remarks

    Jessica Mulroney and Meghan Markle
    George Pimentel/WireImage/Getty Images

    Meghan's longtime friend, Canadian TV star Jessica Mulroney, was recently fired from her I Do, Redo show. Jessica had made threatening remarks to a Black influencer who had called out Jessica's white privilege. Jessica has since apologized, but sources report that Meghan has distanced herself from her friend in the wake of the comments.

  • Prince William's Friendship With One of Kate's Friends

    Kate Middleton
    Splash News

    Even if this story isn't true, people began to look at the couple carefully for cracks after it was alleged that William cheated on Kate Middleton with her friend Rose Hanbury. Whether that's true or not, Kate and Rose were eventually seen hanging out again. So either Kate was quick to forgive, or there was no truth to this story. Still, it was quite a scandal when the rumors first came out.

  • King Edward VIII Abdicated to Marry a Divorcée

    Wallis Simpson and Edward VIII
    Ivan Dmitri/Michael Ochs Archives/Getty Images

    King Edward VIII's romance with the American Wallis Simpson got off to a rough start when they began seeing each other while she was still married. Upon her divorce, Edward planned to marry her, which was forbidden by the Church of England, since she was a divorced woman. Instead of giving Wallis up, Edward abdicated the throne. The position then passed to Queen Elizabeth's father, King George VI, putting her in line for the throne she sits on today.

  • Princess Margaret Fell in Love With a Divorced Man

    Princess Margaret
    Derek Berwin/Fox Photos/Getty Images

    Princess Margaret's love life was full of controversy and sadness. Her first brush with that came when she fell in love with Peter Townsend, a member of the royal staff who was 16 years older than her and a recent divorcé. Margaret had wanted to marry him, but her sister, Queen Elizabeth, forbade it for the same reason that King Edward VIII abdicated: because the Church of England didn't allow for royals to marry people who'd been divorced. That rule was eventually changed, which ended up allowing for Prince Harry to marry divorcée Meghan Markle.

  • Princess Margaret Dated a Man 17 Years Younger

    Princess Margaret and Roddy Llewellyn
    Hulton-Deutsch Collection/CORBIS/Corbis via Getty Images

    In the '70s, the tabloids exposed that Princess Margaret was seeing a 25-year-old gardener named Roddy Llewellyn. He was 17 years younger than her, which was really only half of the scandal. Margaret was still married at the time, adding to the royal family's disgrace in the eyes of the people. The relationship was also used by politicians to attack the status of the royal family. 

    Poor Princess Margaret. 

    Her love life was always causing trouble.

  • Sarah Ferguson Was Caught With an American Financier 

    Sarah Ferguson
    Splash News

    In 1992, four years before Sarah "Fergie" Ferguson's divorce from Prince Andrew, the paparazzi caught her getting cuddly with an American financial advisor named John Bryan. In one infamous photo, Sarah was sunbathing topless while John kissed her feet. She's rebuilt her reputation in the public eye since then, but some of the royals reportedly still haven't forgiven her.

  • Meghan's Dad Is Always Causing Her Trouble

    Thomas Markle
    Splash News

    It's not Meghan's fault that her father's been acting the way he has, but it doesn't make her or the royal family look good. Her dad is almost always bashing her in the press, and Meghan and Harry are even embroiled in a lawsuit over a paper publishing a letter that Meghan wrote to her father. In case anyone was wondering, he also doesn't approve of her stepping back from her royal duties.

  • And Meghan's Half-Sister Causes Just as Much Drama


    Thomas Markle's other daughter, Samantha, is Meghan's half-sister, and Samantha just as much of a non-fan as her father. Their feud has been going on as long as Meghan and Harry's relationship has been in the spotlight, and Samantha misses no chances to take jabs at the duchess. She is reportedly even penning a book, originally titled The Diary of Princess Pushy's Sister. Talk about a problematic family member.

  • Edward VIII Had Ties to Hitler 

    Edward VIII and Wallis Simpson
    Fox Photos/Getty Images

    One of the most despicable friendships the royal family had was Edward VIII's friendship with Adolf Hitler. Edward reportedly called Hitler "not a bad chap," and both Edward and Wallis Simpson visited Hitler in 1937. That would have been long after Hitler opened his concentration camps and began his attacks on Jewish people, among others.

  • Prince Michael's Wife Wore a Racist Brooch

    Princess Michael of Kent
    Mark Cuthbert/UK Press via Getty Images

    Princess Michael of Kent went to the Queen's 2017 Christmas luncheon decked out in a "blackamoor" pin, which is an art style known to romanticize slavery. To make matters worse, Meghan was at the luncheon as her first big outing after her engagement, and that's what she was met with. Princess Michael later apologized for the offense her jewelry caused.

  • Princess Beatrice's Ex Was Arrested on Manslaughter Charges

    Princess Beatrice
    Splash News

    Before dating Beatrice, Paolo Liuzzo had been charged with manslaughter for his involvement in a teenager's death after a drunken fight. His charge was later downgraded, and Paolo was convicted of assault and battery instead. Still, his checkered past reflected poorly on Beatrice. It's no wonder they didn't end up lasting as a couple.

  • Princess Anne's Marriage to Timothy Laurence Started off Scandalous

    Princess Anne and Timothy Laurence
    Max Mumby/Indigo/Getty Images

    Queen Elizabeth's daughter, Princess Anne, was still married to Captain Mark Phillips when she began a romance with a member of the royal staff, Commander Timothy Laurence. It's already quite scandalous for a royal family member to have an affair, much less with a member of the staff. However, Anne and Timothy managed to turn public perception around by marrying and sticking the hard times out. They've been together ever since.

  • A Lover of Princess Diana's Betrayed Her

    James Hewitt
    Evan Agostini/Liaison/Getty Images

    Princess Diana began an affair with her riding instructor, James Hewitt, while still married to Prince Charles. She was later betrayed by James when he spilled details about their romance in the book Princess in Love and later in Love and War. To this day, James is plagued by questions about whether he's Prince Harry's real father. It's been a lifetime of scandal for him and the royal family.

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