Princess Diana and Prince Charles’s Relationship Timeline: Everything You Need to Know

It was a royal romance to remember. Prince Charles and Princess Diana first announced their engagement in February 1981 following a whirlwind courtship—and a belief in modern-day fairy tales was born.

For many, their first introduction to Charles and Diana’s tumultuous relationship, which played out in the 1980s and 1990s, was absorbed via the fictionalized account of it in seasons 4 and 5 of The Crown. But for others, they watched the then-Prince and Princess of Wales fall in love, get married, have babies—Princes William and Harry in 1982 and 1984, respectively—then endure a public and, at times, humiliating split. Of course, this was all ahead of Diana’s tragic and untimely death at the age of 36 in a car crash in Paris in 1997.

Fast forward to present day and the then-Prince Charles is now King Charles III. (His coronation this past May signaled a monumental change for the monarchy given it marked the end of his mother Queen Elizabeth II’s legendary reign.) There’s more: Season six of The Crown is anticipated to debut in late fall on Netflix, barring any impact from the WGA and SAG strikes, which means interest in the royal pair has never been higher.

So, what better time to brush up on a timeline of Charles and Diana’s royal relationship? We put together a clear account of it all, based on interviews and insights from royal experts, but also Charles and Diana themselves.

Before there was Princess Diana, there was Diana’s older sister, Lady Sarah Spencer—now Lady Spencer McCorquodale—who for a brief period, dated the very eligible prince herself. (Their romance reportedly went poof after word got out to the media that Sarah quipped she wouldn’t marry Charles “if he were the dustman of the King of England.”)

Still, Diana’s fate was sealed: At age 16, she joined her older sister for a grouse hunt at her family’s home, Althorp House, where she was first introduced to the prince, who at age 29, was 12 years her senior. Charles spoke of the occasion during their subsequent engagement interview in 1981: “I remember thinking what a very jolly and amusing and attractive 16-year-old she was. I mean, great fun and bouncy and full of life and everything.” Diana’s sister also commented to the media in 1980: “I introduced them. I’m Cupid.”

It was exactly a year later when Princess Diana received a surprise invite to join her sister Sarah at Charles’s 30th birthday at Buckingham Palace on November 14, 1978. Diana—who secretly recorded her take on the events of her marriage on audio tapes for a book, Diana: Her True Story, published by royal biographer Andrew Morton in 1992—revealed that Sarah was actually taken aback that Diana was also invited to the soirée. “Why is Diana coming as well?” Sarah pondered aloud. Diana replied, “Well, I don’t know, but I’d like to come.”

Morton’s book revealed more details about Diana’s reaction to her first major royal party, saying she “had a very nice time at the dance” and that it was “fascinating.” She added: “I wasn’t at all intimidated by the surroundings [at Buckingham Palace]. I thought, amazing place.”

It was barely a year later when Princess Diana received an invite from a mutual friend, named Philip de Pass, to join him at his home with a caveat: Prince Charles would also be joining. In Morton’s book, Diana recounted the exchange via audio tape: “‘Would you like to come and stay for a couple of nights down at Petworth because we’ve got the Prince of Wales staying. You’re a young blood, you might amuse him.’ So, I said, ‘OK.’”

Diana also recalled that Charles was “all over” her during the weekend. “I thought, ‘Well, this isn’t very cool,’” she described. “I thought men were supposed to be not so obvious, I thought this was very odd.”

The timing also likely had an impact. Charles was still reeling from the death of his great-uncle Lord Mountbatten, who was killed by a bomb planted aboard his boat while on holiday in the Republic of Ireland in August 1979. (The IRA later claimed responsibility.) Charles was quite close to Uncle “Dickie,” and the assassination took a toll on the prince. Diana told Morton that the pair spoke of Lord Mountbatten’s funeral, and she thought: “It’s wrong, you’re lonely—you should be with someone to look after you.” Charles invited Diana to join him at Buckingham Palace the next day.

In season four, The Crown had a whole episode devote to a largely fictionalized account of the “Balmoral test,” in which Diana must prove her royal worthiness in the eyes of Charles, but more importantly the late Queen Elizabeth II and Prince Philip, the Duke of Edinburgh. As Diana told Morton, upon receiving an invite to join Charles at Balmoral, the queen’s beloved Scottish estate in Aberdeenshire, she was “shi*ting bricks.” She went on: “I was terrified because I had never stayed at Balmoral, and I wanted to get it right. The anticipation was worse than actually being there. You’re all right once you get in through the front door.”

According to Diana, she spent the bulk of her time at Balmoral in the castle due to the press interest. But her and Charles were able to fit in walks and more: “Charles used to ring me up and say, ‘Would you like to come for a walk, come for a barbecue?’ So, I said: ‘Yes, please.’ I thought this was all wonderful.”

The result was also in: Diana charmed not only the queen, but the entire royal family. In her book, The Diana Chronicles, royal biographer Tina Brown shared the words of Lord Charteris, Queen Elizabeth’s former private secretary: “[Diana] played the prince perfectly.”

Charles continued to “court” Diana into early 1981 with the pair going on 13 dates total (as Diana told Morton) before announcing their engagement to a press pack—and public—that was salivating with interest. The royal news was also the result of pressure inflicted by Charles’s father, Prince Philip, who encouraged Charles to make a choice or risk sullying Diana’s reputation.

Diana discussed the building press intrusion in detail in audio tapes recorded for Morton, saying that it has become almost unbearable to continue to reside in the flat she shared at Coleherne Court in South Kensington with her roommates. She said, “…My three girls were wonderful, star performers: loyalty beyond belief. The feeling [in Sandringham] was I wish Prince Charles would hurry up and get on with it. The Queen was fed up.”

Charles ultimately proposed to Diana during a private dinner at Buckingham Palace on February 6, 1981. As part of an engagement interview with the BBC, they shared additional details about the proposal: “I asked Diana before she went to Australia, two or three days before,” Charles said. “I thought it would be a good idea if she went to Australia, she could think about it and if she didn’t like the idea, she could say she didn’t, or if she did, she could say that.”

But as Diana revealed to Morton, she accepted immediately: “He said, ‘Will you marry me?’ And I laughed. I remember thinking: ‘This is a joke,’ and I said, ‘Yeah, OK,’ and laughed. He was deadly serious. He said: ‘You do realize that one day you will be queen.’ And a voice said to me inside: ‘You won’t be queen, but you’ll have a tough role.’”

Flash-forward a few weeks later to February 24, 1981, when the world learned their happy news and caught their first glimpse of Diana’s sapphire and diamond engagement ring, now worn by Kate Middleton. During their engagement interview with the BBC, the interviewer famously—and now poignantly—asked the royal couple: “Are you in love?” Diana, who was just 19, responded instantly with “Of course!” Charles reflectively added, “Whatever ‘in love’ means.”

The engagement was quick—Charles and Diana were married at St. Paul’s Cathedral on July 29, 1981. More than 600,000 people lined the streets hoping to catch a glimpse of the royal pair with 7.5 million people tuning in from home to watch the televised nuptials.

All eyes were, of course, on the reveal of Diana’s dress, designed by David and Elizabeth Emanuel, and featuring ivory silk, antique lace and 10,000 mother of pearl sequins. There was also a 25-foot train that had to be smushed into the Glass Coach she arrived in with her father, Earl Spencer.

The wedding cost a reported $48 million and also launched what is now a major royal wedding trend: When Diana and Charles forgot to share a kiss during the ceremony, they switched things up and sealed their marriage with a public smooch on the Buckingham Palace balcony. Diana told Morton of her wedding day that although she felt “I was a lamb to the slaughter,” she also remembered “being so in love with my husband that I couldn’t take my eyes off him. I absolutely thought I was the luckiest girl in the world. He was going to look after me.”

The fairy tale feeling reportedly faded fast for Diana: After their wedding day, the royal newlyweds embarked on a three-month honeymoon—including a 12-day cruise aboard the royal yacht Brittania. They traveled to Egypt, but also the Greek Islands, before spending the rest of their time in a hunting lodge at Balmoral Castle. Diana shared with Morton, “I just had tremendous hope in me, which was slashed by day two.”

The age difference was ever-apparent throughout with Charles wanting to devour seven novels by Laurens van der Post, a philosopher and adventurer—and one of Charles’s favorite authors. Per Diana, “He read them, and we had to analyze them over lunch every day.” In the evenings, they hosted important guests aboard and very rarely had time to themselves. Diana’s battle with bulimia was also a factor throughout the trip. “By then the bulimia was appalling, absolutely appalling,” she told Morton. She added: “I remember crying my eyes out on our honeymoon. I was so tired, for all the wrong reasons totally.”

Charles’s relationship with Camilla Parker-Bowles was also a factor. Diana shared via audio tape with Morton that the now-queen was a constant, if inadvertent, presence: “On our honeymoon, for instance, we were opening our diaries to discuss various things. Out come two pictures of Camilla. On our honeymoon, we have our white-tie dinner for President Sadat [of Egypt]. Cufflinks arrive on his wrists—two ‘C’s entwined like the Chanel ‘C’s. Got it in one; knew exactly ‘Camilla gave you those didn’t she?’ He said: ‘Yes, so what’s wrong? They’re a present from a friend.’ And boy, did we have a row.”

The honeymoon was over, but Diana and Charles had baby news to announce: On November 6, 1981, the palace revealed that Diana was expecting and that “the Prince and Princess of Wales, the Queen and the Duke of Edinburgh and members of both families are delighted by the news.”

Prince William Arthur Philip Louis—now next in line to the throne—was born on June 21, 1982, and became the first future king to be born outside palace walls. Charles and Diana famously posed for photos outside the Lindo Wing of St. Mary’s Hospital to huge crowds of onlookers. Diana revealed to Morton that she chose to be induced, sharing via audio tape the main reason: “I couldn’t handle the press pressure any longer, it was becoming unbearable.”

Another significant episode in season four of The Crown shows Diana and Charles embarking on their first royal tour together overseas to Australia and New Zealand. It was reportedly a happier time for the pair, having made the modern decision to bring a one-year-old Prince William along. Diana shared: “That was great—we were a family unit, and everything was fine.”

But the media frenzy over Diana also caused marital strife: Diana shared that crowds were quite vocal over their interest in Diana…and only Diana. “Basically, our tour was a great success,” Diana told Morton. “Everybody always said when we were in the car: ‘Oh, we’re in the wrong side, we want to see her, we don’t want to see him,’ and that’s all we could hear when we went down these crowds and obviously [Charles] wasn’t used to that and nor was I. He took it out on me. He was jealous; I understood the jealousy, but I couldn’t explain that I didn’t ask for it.”

On February 14, 1984—Valentine’s Day—Diana and Charles had more baby news: They were expecting, again. On September 15, 1984, they welcomed Prince Harry Charles Albert David at St. Mary’s Hospital in the same room that William was born two years before. Prince Charles was over the moon: He remarked to crowds waiting outside the steps to the Lindo Wing, “We have nearly got a full polo team now.”

After the birth of their boys, Charles and Diana’s marriage was regularly reported to be on the rocks—so much so that they sat down for a rare joint public interview with ITN on October 20, 1985, with journalist Alastair Burnet. During the conversation, they discussed the immense pressure of being a public figure in the royal realm and alluded to arguments. Charles said, “I suspect most husbands and wives fight, they often have arguments.” Diana immediately shot back: “But we don’t!” Charles replied: “We occasionally do.”

There was more: The world would later learn that 1986 was the year that Charles rekindled his on-again, off-again romance with Camilla Parker Bowles. (She was married to Andrew Parker Bowles at the time.) He revealed to biographer Jonathan Dimbleby in a 1994 documentary that he’d remained faithful to Diana “until it became irretrievably broken down.”

It was reported that 1986 was also the year that Diana began an affair with Captain James Hewitt, which he wrote about in his book, A Love Like No Other: Diana and Me. Charles later told Dimbleby in his biography The Prince of Wales, which published in 1994, that his marriage to Diana “has all the ingredients of a Greek tragedy…I never thought it would end up like this.”

Queen Elizabeth II famously described 1992 as her “annus horribilis,” which translated from Latin means “horrible year.” The events that led to the separation of Charles and Diana were a large reason for that.

Famously featured—and dramatized—in season five of The Crown, on June 16, 1992, biographer Andrew Morton published an earth-shattering biography, Diana: Her True Story, which was full of specifics about the breakdown of her marriage to the Prince of Wales. The book detailed everything from Diana’s battle with bulimia to the role that Camilla played in their marriage. At the time, the sourcing was kept vague—it was only after Princess Diana died in 1997 that Morton revealed that she was the main source for the explosive insights revealed in the book.

The impact of the tell-all was severe—on December 9, 1992, Buckingham Palace announced that Diana and Charles were to separate. “It is announced from Buckingham Palace that, with regret, the Prince and Princess of Wales have decided to separate. The Royal Highnesses have no plans to divorce, and their constitutional positions are unaffected,” British Prime Minister John Major read from a statement on the floor of the House of Commons.

The separation had barely been made official when a British tabloid published a six-minute transcript of a 1989 phone call between Charles and Camilla that came to be known as “Camillagate.” Intimate details about the depth of their relationship were revealed, all of which was covered in season five of The Crown. You could also call a number and listen to the actual tape.

Just over a year later, Charles’s conversation on June 29, 1994, on ITN with Jonathan Dimbleby aired and he confirmed his infidelity. That same night Diana stepped out at the Serpentine Gallery in an off-the-shoulder black dress, now officially dubbed the “revenge dress.” Charles later told Dimbleby in his biography, The Prince of Wales, which published in October that same year that Prince Philip had forced himself into a “loveless” marriage.

It has since been revealed that Princess Diana’s conversation with Martin Bashir on the BBC’s Panorama program, which aired on November 20, 1995, was obtained deceitfully and under false pretenses. Still, in this conversation, Diana concretely revealed her marital unhappiness and how she was treated behind the scenes as she battled an intense eating disorder, post-partum depression and more. Diana also famously remarked about her husband’s extra-marital affair with Camilla: “Well, there were three of us in this marriage, so it was a bit crowded.”

After this interview aired—and with so much dirty laundry aired—the queen wrote the Prince and Princess of Wales and recommended that they both move forward with a divorce.

In February 1996, Diana agreed to Charles’s request for a divorce with a few caveats—that she would continue to be a part of every decision related to her children, Princes William and Harry, and also that she would continue to reside at Kensington Palace and work out of St. James’s Palace. But there’s one more detail she desired: to retain her royal title and be known as HRH Diana, Princess of Wales. When the divorce was finalized, Diana’s HRH status was removed. (She was granted joint custody of the boys and her residency at Kensington Palace.) After a lot of back and forth, the divorce was made official on August 28, 1996.

Following Diana’s divorce from Charles, in July 1997, she struck up a romantic relationship with Dodi Al Fayed, an Egyptian film producer and son of Mohammed Al Fayed, the owner of Harrod’s. (The pair also feature heavily in season five of The Crown.)

On August 31, 1997, during a short trip to Paris, Diana died at the age of 36 following a high-speed car crash in the Pont de l’Alma tunnel. (Dodi was with her and was also killed.) Many factors were thought to be at play and the reason for the tragedy: The group was being chased by paparazzi, desperate for photos of Diana and Dodi, but Henri Paul—the driver of the vehicle—was also legally drunk at the time of the incident.

Charles flew to Paris with Diana’s two sisters, Lady Jane Fellowes and Lady Sarah McCorqodale, to bring her body home to London. Upon her passing, Tony Blair, who was prime minister at the time, declared Diana the “people’s princess” adding that that was “how she will stay, how she will remain, in our hearts and in our memories forever.”