Inside Princess Diana's Complicated Friendship with Sarah Ferguson, Duchess of York

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All eyes are now on royal sisters-in-law Kate Middleton and Meghan Markle, but more than 30 years ago it was Diana, Princess of Wales and Sarah, Duchess of York taking center stage. The two women had a complex relationship, which over the years saw them as rivals, best friends, and everything in between.

How did they meet?

The relationship between Diana and Sarah actually started long before they were both members of the royal family, as the two women were actually fourth cousins. (They were both descended from William Cavendish, Fourth Duke of Devonshire.) Their mothers were also in school together, and they had known each other since adolescence—although they only became close after they reconnected in 1980, when Diana was 19 and Sarah was 21. The two young women shared a lot of the same friends and many of the same interests, and were soon lunching together every week.

A deepening bond

Diana invited Sarah to her wedding and gave her a piece of fabric to have made into a dress for the event, but Sarah—who attended the historic occasion alone—later said she felt snubbed not to be invited to the post-ceremony reception. After the wedding, the pair continued to meet weekly for lunch, and Sarah was a confidante to Diana as she struggled with her new role in the royal family. Diana would often call her friend, who would visit her at Buckingham Palace to cheer her up, and Sarah recommended her astrologer to Diana. Sarah later wrote in her 1996 autobiography, “She was two years younger than I, and I strove to support and protect her as I would a younger sister—as I still do today, as a best friend.”

The matchmaker princess

The Queen often hosts "dine and sleep" events at Windsor Castle during Ascot week, and in 1985 Sarah Ferguson attended one of the glittering occasions after Diana had recommended her to the Queen for an invite. Sarah found herself seated next to Prince Andrew at dinner. The pair had crossed paths socially over the years, but it wasn’t until this point that romance blossomed, and they started dating. Diana further acted as cupid by inviting the couple to stay at Highgrove, the country house she shared with Charles, before the relationship was made public. Later Sarah was brought deeper into the royal fold when she vacationed with Charles and Diana at the Swiss ski resort of Klosters while Andrew was away at sea.

Diana as a royal guide

As Andrew and Sarah’s relationship became more serious, she made her first appearances with the royal family. These caused Fergie much anxiety, but Diana was on-hand to help. The princess loaned her friend a a dress, and accompanied her to the event. Sarah later explained in her autobiography My Story that she was especially nervous of the assembled photographers, recalling: “I looked over at my friend in befuddlement. ‘Just keep smiling’ Diana whispered. And I did, as I would for long years to come. I always felt safe in mimicking Diana.”

Royal sisters-in-law

Sarah was the first female member of the royal family to have a bachelorette party. Fergie, Diana and a group of their friends dressed as police women, but got themselves into trouble with the authorities for causing a scene outside Buckingham Palace. After the misunderstanding was straightened out, they went on to society club Annabel’s and later locked Prince Andrew out of the Buckingham Palace gates as he returned from his bachelor party.

Over the years Sarah brought out Diana’s cheeky, fun side—often with disapproval from others, including members of the family. The two women were criticized in the press for poking their friend Lulu Blacker in the backside with their umbrellas at Ascot, and by Prince Charles for mock-fighting in the snow during a photo call at Klosters. One summer night at the Queen’s Scottish home Balmoral the two women rode together on a quad bike across the golf course in the long evening gowns they had worn for dinner, and then took the Queen Mother’s Daimler for a high-speed spin—to the disapproval of Princess Anne.

A fierce rivalry

Though Diana and Sarah were close, but they were also young, sensitive, and insecure in both themselves and their royal positions, which led to a certain amount of rivalry. Sarah impressed the Queen soon after her wedding in 1986 by getting her pilot’s license; won over Prince Philip by taking up open carriage driving, one of his favorite past-times; and excelled at the kind of sports that the royals love but Diana wasn’t good at, including skiing and horseback riding. Diana revealed to her biographer Andrew Morton, that Fergie “wooed everybody in this family and did it so well. She left me looking like dirt.” The princess added that Prince Charles told her “I wish you would be like Fergie—all jolly.”

Falling out of royal favor

As Diana and Sarah became more unhappy in both their marriages and the royal court, they increasingly leaned on each other for support. In her autobiography, Sarah wrote that 1991—the year before their respective marital separations—“It was the year we first put words to the unspeakable idea that had been nudging us in the ribs for some time: that one or both of us might leave the royal family. We burned the phone wires into the night, trading secrets and jokes that no-one else would understand.”

The single life

After they both separated from their husbands in 1992, Diana and Sarah were as close as ever. They would still meet for lunch, or Sarah would bring her daughters for tea with Diana, William, and Harry at Kensington Palace. After Sarah’s divorce was finalized in May and Diana’s in August 1996, they vacationed together in the South of France with their children.

Falling out for good

Sarah said years later that when Diana stopped speaking to her in 1996 that she had no idea why, but it’s thought that Diana was unhappy about the way her former sister-in-law wrote about her in her autobiography, which came out in the November of that year. One of the things to which Diana reportedly objected to is the detail that Diana gave Fergie several pairs of shoes, "and less happily her plantar warts."

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Diana's death

When Diana died in August 1997, the pair had not reconciled. Sarah attended her old friend’s funeral and later told Harper’s Bazaar, “Because we were like siblings... we rowed. And the saddest thing, at the end, we hadn't spoken for a year."

"I tried, wrote letters, thinking whatever happened didn’t matter, let's sort it out," Ferguson continued. "And I knew she’d come back. In fact, the day before she died she rang a friend of mine and said, 'Where’s that Red? I want to talk to her.'"

The next generation

Sarah’s relationship with Diana’s sons William and Harry has been mostly distant over the past few decades, but there have been some changes in recent years. It’s thought that William didn’t have a great deal of warmth for his former aunt, as he didn’t invite her to his wedding.

“I didn’t think I was probably worthy to go to their wedding,” she later town Town & Country. “I took myself to Thailand, actually, to be far away from it so that I could try and heal.”

However Harry has spent time with Sarah in recent years, vacationing in the Swiss ski resort of Verbier in 2013 with his former aunt, uncle Andrew, cousins Beatrice and Eugenie, and then-girlfriend Cressida Bonas. When Harry married Meghan Markle in May 2018, Sarah was invited to see her former nephew take his vows, seating in the quire of the church near the rest of the royal family.

"I believe that Diana would be so proud of her boys," she told T&C, "and she’d be so proud of her grandchildren."

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