Prince Harry & Princess Margaret: All The Details About Their Relationship

The following article contains references to drug abuse, alcohol abuse, and suicide.

At first glance, Prince Harry and the late Princess Margaret might not seem to have a lot in common. Born in 1930, Margaret was from a traditional generation of royals that prioritized duty over all else. Throughout her childhood, Margaret was shielded from the prying eyes of the press, thanks to her mother's efforts to keep the details of palace life under wraps. As royal expert A.N. Wilson once wrote, the world that Margaret and her sister, Queen Elizabeth II, inhabited could be described as a "cocoon of unknowability." However, even in private, royals enforced protocol. Per royal nanny Margaret Crawford's book, "The Little Princesses," Elizabeth and Margaret lived in a bubble in which "the royal discretion held" firm.

In sharp contrast to Margaret's upbringing, Harry was raised in a new generation of royals that was thrust into the spotlight. Hours after he was born, Harry was presented to the press on the steps of St. Mary's Hospital, and by the time he was 8 years old, international tabloids were debating the sanctity of his parents' marriage. While protocol was still relevant in Harry's upbringing, the young prince was often found challenging these royal rules.

While Harry and Margaret essentially came from different universes, growing up in such vastly different times, they both fully understood what it was like to be the palace spare. Consequently, the pair forged an unusual relationship — one that left the prince wishing that he and his great-aunt had gotten more time to bond.

Prince Harry and Princess Margaret might not always have had the closest bond, but that doesn't mean that Margaret never tried to bond with her nephew. In his book, "Spare," Harry recounted a time when the princess tried to connect with him via an admittedly bizarre holiday present. Per the prince's recollections, Margaret gave him a decorated ballpoint pen one Christmas. She apparently told him, "I do hope you like it." Unfortunately, Harry explained that his younger self did not understand the gift, prompting Margaret to try to defend it. The Duke of Sussex recalled, "But it wasn't just any biro, [Margaret] pointed out. It had a tiny rubber fish wrapped around it."

Despite the princess' best efforts, the young Harry didn't see this moment as one of connection — nor did he consider the significance of a writing utensil as a present for a young boy. While he responded to the present, telling his great-aunt, "Oh. A fish biro! OK,'" he revealed that he said to himself, "That is cold-blooded."

The gift didn't exactly sit right with the prince, but the princess did have a habit of giving people unusual presents. Apparently, she was very careful about choosing something unique for each person. Even so, she often missed the mark. Chatting with The Telegraph, Margaret's lady-in-waiting, Lady Anne Glenconner, revealed, "Though she went to a lot of trouble, you never quite knew what you were going to receive. Sometimes we'd be given handbags that had clearly been worn by her."

It is no secret that Princess Margaret and Princess Diana did not get along. As royal expert Gareth Russell wrote in his book, "Do Let's Have Another Drink," Margaret had such a bad impression of Diana that she refused to refer to her directly. Instead, she would apparently call her "the girl who married my nephew." Despite all the bad blood flowing between the two princesses, they were actually quite alike.

In, "Spare," Harry confessed that his vision of his great-aunt evolved considerably after his childhood, and he even drew comparisons between Margaret and Diana: "Aunt Margo also wasn't that dissimilar from Mummy." The prince continued, writing, "Both rebels, both labeled as sirens." Indeed, both Margaret and Diana deviated from their expected roles by pursuing extramarital affairs. During her ill-fated marriage to Antony Armstrong-Jones, Margaret went out with winemaker Anthony Barton. Similarly, Diana had lovers of her own, including an intense relationship with military officer James Hewitt. 

Ultimately, both Diana and Margaret ended their respective marriages, breaking protocol and becoming divorced princesses. The press reacted explosively to the resulting scandals. Margaret was portrayed as selfish, while Diana was accused of being attention-hungry, with one 1995 Women's Wear Daily article alleging that she'd "always longed to take her place in the front row."

Perhaps because they were both second in line to the throne, Princess Margaret and Prince Harry were given more freedom than their older siblings. Throughout the 1960s, Margaret partied with some of the biggest names in Hollywood, including Barbara Streisand, Marlon Brando, and Elizabeth Taylor. Just like his great-aunt, Harry has been known to rub shoulders with celebrities. The prince is even rumored to receive drunk texts from Cara Delevinge. 

With Hollywood-style parties, however, comes a massive culture of excessive alcohol consumption. According to the book, "Ma'am Darling: 99 Glimpses of Princess Margaret" by royal expert Craig Brown, Margaret became so entrenched in booze and tobacco that she even invented a way to do both at the same time. Apparently, the princess "tried to combine the smoking and drinking by gluing matchboxes onto tumblers, so she could strike matches while drinking."

Harry, too, has abused alcohol. In his docu-series, "The Me You Can't See," Harry told Oprah Winfrey, "I would probably drink a week's worth in one day on a Friday or a Saturday night. ... I was willing to drink, I was willing to take drugs." Interestingly, both Harry and Margaret eventually committed to living a healthier lifestyle. While Harry quit drinking in order to maintain his relationship with Meghan Markle, Margaret did so temporarily out of concern for her health.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Royal life can take its toll, and Princess Margaret and Price Harry both faced a lot of pressure in their public roles. Ultimately, great-aunt and great-nephew alike reported struggling with their mental health. In 1967, as Margaret's marriage to Anthony Armstrong-Jones was deteriorating, the princess reportedly experienced symptoms of psychological distress.

In an article for the Daily Mail, royal expert Andrew Morton explained that Margaret contemplated suicide. Per Morton's account, "Margaret had phoned a friend while he was hosting a party, threatening that if he did not check on her immediately, she would throw herself from her bedroom window." When the friend called Queen Elizabeth, the monarch seemed unconcerned, apparently telling him, "Carry on with your house party. Her bedroom is on the ground floor."

While some believe that Margaret's mental health challenges were never officially diagnosed, the same cannot be said about Harry. In his memoir, "Spare," the Duke of Sussex wrote, "I was an agoraphobe. Which was nearly impossible given my public role." The prince went on to describe having a panic attack in front of his brother. "Him of all people. He'd been present for my very first panic attack. With Kate," he explained. Additionally, Harry has been diagnosed with post-traumatic stress disorder (PTSD).

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

Although Prince Harry and Princess Margaret had a lot in common, the pair did not have much of an opportunity to discuss their similarities. On February 9, 2002, Margaret died in her sleep following a series of strokes. At the time, Harry was only 17 years old. He would never get the chance to talk to his great-aunt about falling in love with Meghan Markle, nor would he ever get to go to her for advice. Despite all of the similarities between Margaret and Harry, the pair did not have enough time to connect on all of these points.

In his memoir, Harry mourned the adult relationship that he and Margaret were never able to build. "It struck me that Aunt Margo and I should've been friends," he wrote. "We had so much in common. Two Spares." Margaret once opined that she was born too late, but perhaps author Jenny Diski put it best: "She was born too early."