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The Crown season is finally upon us again, and the show’s fifth season is packed with juicy, compelling royal drama of the early 1990s. Of course, most of it revolves around Charles and Diana—now played by Dominic West and Elizabeth Debicki—their tempestuous rollercoaster of a relationship and their very public separation.
Here’s a timeline of their romance as it really happened, from that brief first meeting all the way through to their bitter divorce.
This was the year Charles first met Diana, when she was 16 (she’s 12 years his junior). Their meeting took place while Charles was dating Diana’s older sister, Sarah—years later, Sarah would declare herself “Cupid,” since she was the one who first introduced them. The couple met at Althorp, the Spencer family home, while Charles was visiting for a casual grouse hunt. During their engagement interview four years later, Charles described his first impression of Diana: “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.”
Charles and then-fiancée Diana at Balmoral in May 1981.
Tim Graham//Getty Images
Three years on from their initial meeting, Charles and Diana reconnected when they were both staying at the home of a mutual friend, Philip de Pass. Charles was mourning the loss of his great uncle and mentor, Lord Mountbatten, who had been assassinated less than a year earlier. Diana, in a characteristic moment of compassion, felt sorry for the grieving Charles.
“He’d just broken up with his girlfriend and his friend Mountbatten had just been killed. I said it would be nice to see him,” Diana explained in the 2017 documentary Diana: In Her Own Words. “We were talking about Mountbatten and his girlfriend and I said, ‘You must be so lonely.’ I said, ‘It’s pathetic watching you walking up the aisle with Mountbatten’s coffin in front, ghastly, you need someone beside you.’ Whereupon he leapt upon me and started kissing me.”
In Jonathan Dimbleby’s authorized biography of Prince Charles, The Prince of Wales, published in 1994, Charles revealed Prince Philip pressured him to marry Diana.
February 3, 1981
After just a few months of dating, Charles proposed to Diana in the nursery at Windsor Castle. Diana described the moment in some depth to Andrew Morton for his 1992 biography Diana: Her True Story—In Her Own Words. “[Charles] said, ‘Will you marry me?’ and I laughed,” she recalled. “I remember thinking, ‘This is a joke,’ and I said, ‘Yeah, OK,’ and laughed. He was deadly serious.”
Diana was ecstatic, she recalled in the documentary. “I said, ‘I love you so much, I love you so much.’ And he said, ‘Whatever love means.’ Said it then. So I thought that was great, I thought he meant that,” she explained. “In my immaturity, which was enormous, I thought that he was very much in love with me, which he was. He sort of had the besotted look about him looking back at it, but it wasn’t the genuine sort.”
February 24, 1981
Charles and Diana announce their engagement to the world and give their first public interview as a couple. Asked by the interviewer how he’s feeling, Charles says he’s “just delighted, and happy. I’m amazed that she’s been brave enough to take me on!” Then, when the interviewer presses them on whether they’re in love, Diana quickly responds, “Of course!” But Charles, echoing his not-so-comforting words from a few weeks prior, says, “Whatever ‘in love’ means.”
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Princess Diana’s engagement interview (best quality)
Diana laughs this off in the moment, but years later she admitted the remark upset her. In audio featured in the 2017 documentary Diana: In Her Own Words, she called the interview “ghastly” and recalled that Charles’ comment “threw [her] completely. I thought, what a strange answer. God, absolutely traumatized me.”
March 9, 1981
Diana attends her first public engagement with Prince Charles as his fiancee. The event—a recital at London’s Goldsmith’s Hall in aid of the Royal Opera House Development Appeal—marked the first time Diana’s style came under intense scrutiny from the press.
Charles and Diana arrive at a banquet held in Goldsmith’s Hall in London in March 1981.
In his biography, Morton wrote: “She chose a black ballgown with plunging, gravity-defying décolletage, which had commentators wondering if she had exposed more than she should, for a charity gala in the presence of Princess Grace of Monaco, the former Hollywood star Grace Kelly.” This was the first time Diana wore an Emanuel gown—the husband-and-wife designers would go on to create her iconic wedding gown.
Diana recalled the event as “a horrendous occasion,” during which she felt self-conscious about not knowing royal protocol. “I didn’t know whether to go out of the door first. I didn’t know whether your handbag should be in your left hand not your right. I was terrified, really—at the time everything was all over the place.” Grace Kelly reportedly sensed Diana’s nervousness and took her aside, jokingly telling her: “Don’t worry. It will get a lot worse.’”
July 27, 1981
On the Monday before her wedding day, Diana made a chilling discovery: a beautiful bracelet her future husband intended to give to another woman. The woman in question was his former girlfriend Camilla Parker Bowles, with whom he remained close. According to Morton, Diana considered calling off the wedding after discovering the bracelet, which confirmed her worst suspicions about Charles’ relationship with Camilla.
But at a lunch with her older sisters, Sarah and Jane, Diana was persuaded that she had to go through with the wedding. “She was confused, upset and bewildered by the train of events,” Morton wrote. “At that moment, as she seriously considered calling off the wedding, they made light of her fears and premonitions of the disaster which lay ahead. ‘Bad luck, Duch,’ they said, using the family nickname for their younger sister, ‘your face is on the tea-towels now so you’re too late to chicken out.’”
July 29, 1981
Princess Diana Archive//Getty Images
Charles and Diana were married in a lavish ceremony at St. Paul’s Cathedral in London. The event was watched by a global television audience of 750 million across 74 countries, and more than 600,000 people flocked to the streets of London in person, hoping to catch a glimpse of the newlyweds.
Despite her misgivings, Diana recalled being blissfully happy on her actual wedding day. “I remember being so in love with my husband that I couldn’t take my eyes off him,” she said in Morton’s biography. “I just absolutely thought I was the luckiest girl in the world. He was going to look after me. Well, was I wrong on that assumption.”
Maybe unsurprisingly, the honeymoon period didn’t even last through the actual honeymoon. Diana discovered that Camilla had given Charles a set of cufflinks, and the design only reinforced her fears about their relationship. “On our honeymoon, cufflinks arrive on his wrists,” Diana told Morton. “Two C’s entwined like the Chanel ‘C.’ Got it. One knew exactly [what it meant]. So I said ‘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. Jealousy, total jealousy. And it was such a good idea the two C’s, but it wasn’t that clever.”
June 21, 1982
David Levenson//Getty Images
Diana gave birth to her first son, Prince William, at St. Mary’s hospital in London.
Charles and Diana embarked on their first overseas royal tour as a couple, visiting Australia and New Zealand with the 10-month-old Prince William.
The couple’s schedule was packed with galas, polo matches, photo opportunities, and charity balls—and though she was only 22, it was already clear that Diana’s star was beginning to outshine her husband’s. Diana pulled in huge crowds during their tour, and Charles was well aware that he wasn’t the main attraction. “They’ve come out to see my wife, they haven’t come out to see me,” he reportedly told aides, according to Tatler.
Tim Graham//Getty Images
By bringing baby Prince William along on the tour, Charles and Diana changed royal rules in a significant way. Protocol dictates that two heirs should not travel together on the same trip, in order to protect the line of succession. Bringing William only bolstered Diana’s popularity with the Australian public, and in particular mothers who related to her. The popularity of the monarchy was in decline in Australia at the time, with republicanism on the rise and new prime minister Bob Hawke openly stating that he felt the country would be better off as a republic—but Diana was so beloved that this began to change. According to BBC History magazine, it was reported at the time that Diana and Charles’ popularity had set back the possibility of Australia becoming a republic by “two decades.” (A line also referenced in The Crown’s fourth season.)
September 15, 1984
Diana gave birth to Prince Harry following a pregnancy that was described as “difficult.” and a nine-hour labor. Her morale wasn’t helped much by the comment Charles made just after the birth, as she recounted to Morton. “Charles always wanted a girl,” Diana said. “Harry was a boy. [Charles’] first comment was, ‘Oh God, it’s a boy.’ His second: ‘And he’s even got red hair.’” Diana took this personally, since red hair runs in her family, and the tense moment was a harbinger of an increasingly unhappy marriage.
Tim Graham//Getty Images
Diana later described Charles’ reaction to Harry’s birth as the beginning of the end for their marriage. “Charles and I were very, very close to each other the six weeks before Harry was born, the closest we’ve ever, ever been and ever will be,” she told Morton, per Good Housekeeping. “Then, suddenly, as Harry was born, it just went bang, our marriage. The whole thing went down the drain.”
Although they remained close throughout Charles’ marriage to Diana, it’s not clear exactly when Charles and Camilla began a physical affair. According to People, though, it was in the year 1986.
Also this year, Charles wrote of his marriage in letters later revealed in Dimbleby’s book, “How could I have got it all so wrong?” and “How awful incompatibility is, and how dreadfully destructive it can be for the players in this extraordinary drama. It has all the ingredients of a Greek tragedy…I never thought it would end up like this.”
After several increasingly tense years, during which it became clear to Diana that Charles was still involved with his ex, Diana confronted Camilla at a party.
In her interview with Morton, per CBS News, here’s how Diana recalled the exchange:
Diana: “I know what’s going on between you and Charles, and I just want you to know that.”
Camilla: “You’ve got everything you ever wanted. You’ve got all the men in the world [to] fall in love with you and you’ve got two beautiful children, what more do you want?”
Diana: “I want my husband. I’m sorry I’m in the way, and it must be hell for both of you. But I do know what’s going on. Don’t treat me like an idiot.”
August 23, 1992
Though it’s long been rumored that Diana had extramarital affairs, this was publicly confirmed for the first time in 1992, when the tabloid newspaper The Sun published a transcript of a private phone conversation between Diana and James Gilbey. In addition to the implication that Diana and Gilbey were having an affair—he called her by the pet name “Squidgy”—the transcript saw Diana talking candidly about her miserable marriage to Charles.
Charles and Diana on their last official trip together, to South Korea, in November 1992.
Tim Graham//Getty Images
December 10, 1992
Charles and Diana officially separate, having been estranged in private for some time. Prime Minister John Major made the announcement to the nation before the House of Commons, and stated that the couple would not be divorcing, and would continue their royal duties separately. “This decision has been reached amicably and they will both continue to participate fully in the upbringing of their children,” Major said.
But despite the emphasis on amicability, Diana and Charles’ split soon descended into a bitter battle for public sympathy which Newsweek dubbed “The War of the Waleses” in 1996.
Charles publicly admitted to his infidelity for the first time during an interview with British journalist Jonathan Dimbleby. As reported by The New York Times, Charles was asked whether he had been faithful throughout the marriage. He responded, “Yes… Until it became irretrievably broken down, us both having tried. It is a deeply regrettable thing to happen, but it does happen, and unfortunately, in this case, it has happened.”
On the same night that the interview was broadcast, Diana attended a gala at the Serpentine Gallery in Kensington Gardens, wearing a show-stopping outfit that would soon become infamous. A short, off-the-shoulder black number with a plunging neckline, an asymmetrical hem and a dramatic flowing train, it was dubbed Diana’s “revenge dress,” because she chose it knowing only too well that Charles would be publicly admitting to his affair with Camilla that same evening.
Princess Diana Archive//Getty Images
Designer Christina Stambolian recalled Diana walking into her boutique and asking for “a special dress for a special occasion.” In the book Diana: A Life in Dresses, Stambolian describes Diana’s emotions at the time by referencing her favorite ballet, Swan Lake. “I was thrilled to see Diana wear it on that night of all nights,” Stambolian said. “She chose not to play the scene like [Swan Lake’s] Odette, innocent in white. She was clearly angry… She wore bright red nail enamel, which we had never seen her do before. She was saying: ‘Let’s be wicked tonight.’”
It was Diana’s turn to tell her side of the story, in her first ever public solo interview. During the now-legendary (and controversial) interview with the BBC’s Martin Bashir, Diana discussed her struggle with bulimia and Charles’ infidelity, saying bluntly: “There were three of us in this marriage, so it was a bit crowded.”
Diana also admitted to Bashir that she had been unfaithful to Charles, confirming specifically that she had been involved with cavalry officer James Hewitt for several years. “Yes, I adored him. Yes, I was in love with him,” she said of Hewitt. “But I was very let down.”
August 29, 1996
Four years after their split was announced, Charles and Diana’s divorced was finalized. In its report, The New York Times noted that the divorce “brings to a close a long relationship that started with hope and ceremony and deteriorated into misunderstanding, bitterness and all-out war.” The divorce agreement stipulated that Charles would no longer pay any of Diana’s bills, leaving her to pay her own hefty divorce expenses.
On the same day the divorce was confirmed, Buckingham Palace announced a new rule stipulating that anyone who obtained a royal title through marriage would lose that title upon their divorce. At the time, this affected only Diana and Sarah Ferguson, who had recently divorced Prince Andrew.
Shortly before Diana’s tragic death in a car accident in Paris on August 31, 1997, the princess lunched with Anna Wintour and then-The New Yorker editor Tina Brown. In Brown’s book The Diana Chronicles, published in 2008, she writes that Diana and Charles were getting along quite well before Diana’s death.
“Charles got into the habit of dropping in on her at Kensington Palace and they would have tea and a sort of rueful exchange,” Brown wrote. “They even had some laughs together.
“It was definitely calming down, the boys were older. They talked about their philanthropies. And she had accepted Camilla. One thing she had finally done was really understand that Camilla was the love of his life, and there was just nothing she could do about it…But she said to me at that lunch that she would go back to Charles in a heartbeat if he wanted her.”
Emma Dibdin is a freelance writer based in Los Angeles who writes about culture, mental health, and true crime. She loves owls, hates cilantro, and can find the queer subtext in literally anything.