From their first encounter to their tragic end, here’s every relationship milestone in Prince Charles and Princess Diana’s complex history

Photo: Tim Graham Photo Library

Prince Charles and Princess Diana’s love may not have stood the test of time, but their stories will forever be intertwined.

The couple were first introduced in 1977 by Princess Diana’s sister, Lady Sarah McCorquodale (née Spencer), who recounted the moment to The New York Times. “He met Miss Right and she met Mr. Right,” Sarah said. “They just clicked. They have the same giggly sense of humor, and they both love ballet and opera and sport in all forms. It’s perfect, and they are both over the moon about it.”

It wasn’t until three years later that Charles and Diana met again and began dating. After a whirlwind courtship, the pair wed in a lavish and highly publicized ceremony at St. Paul’s Cathedral in London. But Diana would later reveal to her astrologer, Penny Thornton, that the wedding almost didn’t happen.

“One of the most shocking things that Diana told me was that the night before the wedding, Charles told her that he didn’t love her,” Thornton said in an ITV documentary. “I think Charles didn’t want to go into the wedding on a false premise. He wanted to square it with her and it was devastating for Diana. She didn’t want to go through with the wedding at that point, she thought about not attending the wedding.”

Instead, Diana said her vows but later stated it was the “worst day of [her] life” to her friend and voice coach, Peter Settelen. “If I could write my own script I would have my husband go away with [Camilla Parker Bowles] and never come back,” she said in a recording per The Independent, which was released as part of a Channel 4 documentary.

Never-Before-Seen Photo of Princess Diana Unveiled at Her Former Palace Home

The couple would go on to share a tumultuous 15 years together, during which they welcomed two sons, Prince William in 1982 and Prince Harry in 1984.

The union was one marred by jealousy: In 1995, Diana told the BBC that Charles resented the attention she received from the public.

By 1986, the couple’s relationship was seemingly beyond the point of repair. That year, Charles wrote in a letter that he felt “in a kind of cage … longing to be free,” according to AP News. Diana’s former riding instructor, ex-army Major James Hewitt, later claimed that he had begun an affair with her around the same time.

The couple separated in 1992 and their divorce was finalized just one year before Diana’s death on Aug. 31, 1997, when she was tragically killed in a car crash.

From their lavish wedding to raising two sons in the spotlight, here is a timeline of Prince Charles and Princess Diana’s relationship.

1977: Prince Charles and Diana Spencer are introduced by Lady Sarah

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The Prince of Wales and the former nanny first made each other’s acquaintance at Althorp, the Spencer family home, as Diana would later recall to the BBC. “It was 1977. Charles came to stay as a friend of my sister Sarah for a shoot,” she said, joking, “We sort of met in a plowed field.”

“I remember thinking what a very jolly and amusing and attractive 16-year-old she was,” Charles, who was 29 at the time of their introduction, recalled. “I mean, great fun, and bouncy and full of life and everything.”

When asked about her first impression of Charles, Diana simply replied, “Pretty amazing.”

November 14, 1978: Diana attends Prince Charles’ 30th birthday party

Despite seemingly hitting it off during their first meeting, it would be more than a year before Charles began courting Diana. In the meantime, Charles briefly dated Diana’s sister.

In audio recordings made by Diana at Kensington Palace, which would ultimately serve as the basis for her 1992 biography, she recalled attending Charles’ 30th birthday dance on Nov. 14, 1978. “I had a very nice time at the dance — fascinating,” she reportedly recounted in the audio files.

July 1980: Prince Charles and Diana bond at the home of a mutual friend

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Diana received an invite from mutual friend Philip de Pass to stay at his home in July 1980, when Prince Charles would also be staying.

“‘Would you like to come and stay for a couple of nights down at Petworth [in West Sussex, England], because we’ve got the Prince of Wales staying,’ ” she remembered de Pass saying, per the Daily Mail. “‘You’re a young blood — you might amuse him.’ So I said: ‘OK.’ “

During their stay, Charles and Diana bonded over his grief at the loss of his great-uncle Lord Mountbatten, the Daily Express reported.

1980: Prince Charles courts Diana

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After that trip, the Prince of Wales continued to court the young Diana. “We met 13 times and we got married,” she revealed in her tapes, according to ABC News.

Charles told the BBC he “gradually” knew that Diana was “the one” in their engagement interview.

“I suppose towards the end of the summer, the autumn, last year,” Charles said. “I began to realize what was going on in my mind, and hers, in particular. And all these things help. But you know, it was a gradual business.”

February 1981: Prince Charles proposes to Diana

Prince Charles popped the question to his future bride during a private dinner at Buckingham Palace in early February 1981. He would later recount the event to the BBC during their engagement interview.

“I asked Diana before she went to Australia,” he said. “Two or three days before. I thought it would be a good idea … if she went to Australia she could then 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.”

The future princess later shared that saying “yes” was the obvious choice. “I had a long time to think about it because I knew the pressure was on both of us,” she said. “It wasn’t a difficult decision in the end. It’s what I wanted. It’s what I want.”

February 24, 1981: Prince Charles and Diana announce their engagement

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The couple shared their happy news with the world on Feb. 24, 1981, with a formal announcement by the palace. “It is with the greatest pleasure that the Queen and the Duke of Edinburgh announce the betrothal of their beloved son the Prince of Wales to the Lady Diana Spencer, daughter of Earl Spencer and the Honourable Mrs. Shand Kydd,” the statement read.

The pair also posed for photos, with Diana wearing the famous sapphire-and-diamond engagement ring — which now belongs to Kate Middleton — and spoke to the BBC about their state of mind.

“[I’m] delighted and happy. I’m amazed that she’s been brave enough to take me on,” Prince Charles said.

When asked if they were in love, Diana replied, “Of course,” while Charles replied, “Whatever in love means” — an answer that “traumatized” his 19-year-old fiancée, she would later divulge.

June 13, 1981: Diana attends her first Trooping the Colour ceremony with Prince Charles

Princess Diana broke the “no ring, no bring” policy at the 1981 Trooping the Colour ceremony. She attended the event one month ahead of her wedding to Prince Charles.

The day took a dark turn when 17-year-old Marcus Simon Sarjeant fired blanks at Queen Elizabeth until he was wrestled to the ground by police. This incident led to security concerns for Charles and Diana’s upcoming wedding.

July 29, 1981: Prince Charles and Princess Diana are married

Princess Diana and Prince Charles.

The duo tied the knot in an epic event that would be declared a public holiday and cost the palace a jaw-dropping $48 million, according to Smithsonian magazine. They exchanged their vows at St. Paul’s Cathedral in London, making Diana the first British woman to marry an heir to the throne in 300 years.

A crowd of 3,500 people waited outside the cathedral, and more than 600,000 people lined the streets in hopes of catching a glimpse of the newlyweds. Meanwhile, 7.5 million more tuned in at home to watch the nuptials.

The bride wore an ivory silk and antique lace gown by David and Elizabeth Emanuel that featured a record-breaking 25-foot train and 10,000 mother of pearl sequins.

Their vows broke tradition, as Diana elected, with Charles’ support, to omit the word “obey” from the traditional vows, The New York Times reported. Though Charles and Diana didn’t share a kiss during the ceremony, they made up for it when they shared a public liplock on the Buckingham Palace balcony.

Afterward, guests were treated to 27 wedding cakes and Suprême de Volaille Princesse de Galles, or “Princess of Wales Chicken Supreme.”

Diana later recounted the day to biographer Andrew Morton. “I remember being so in love with my husband that I couldn’t take my eyes off him,” she said. “I just absolutely thought I was the luckiest girl in the world. He was going to look after me.”

August 1981: Prince Charles and Princess Diana go on their honeymoon

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The newlyweds kicked off their three-month-long honeymoon with a 12-day cruise aboard the royal yacht Brittania, upon which they traveled to Egypt and the Greek islands. The rest of their time was spent in a hunting lodge at Balmoral Castle in Scotland. In an August 1981 letter to her personal secretary Jane Parsons, Diana wrote, “The honeymoon was a perfect opportunity to catch up on sleep.”

October 1981: Princess Diana makes her first official visit to Wales with Prince Charles

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Diana’s popularity quickly became apparent during her first visit to Wales as Princess. “[Diana] sort of metamorphosed into a very, very elegant blonde beauty,” the Queen’s cousin, Lady Elizabeth Anson, later told PEOPLE. “They did a visit to Wales which was the beginning of, for Prince Charles, realizing, ‘They’ve come out to see my wife, they haven’t come out to see me.’ “

November 4, 1981: Prince Charles and Princess Diana attend their first State Opening of Parliament together

Diana sat alongside her new husband at their first State Opening of Parliament, marking their first major state occasion since their wedding. She opted for a white, puff-sleeve gown with long gloves, while Charles wore full military regalia.

November 6, 1981: Prince Charles and Princess Diana announce they are expecting

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Less than four months after tying the knot, the royal couple announced that they would soon be parents.

“The Prince and Princess of Wales, the Queen and the Duke of Edinburgh and members of both families are delighted by the news,” a spokesperson for the palace said per The New York Times. “The Princess is in excellent health. The Princess hopes to continue to undertake some public engagements but regrets any disappointment which may be caused by any curtailment in her planned program.”

June 21, 1982: Prince Charles and Princess Diana welcome their first son

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Prince William Arthur Philip Louis was born on June 21, 1982. The proud parents posed for pictures with the baby outside St. Mary’s Hospital in London.

Though Charles reportedly pushed to name their son Arthur, historian Robert Lacey told PEOPLE in October 2021 that “Diana, Princess of Wales proposed a more robust name — William, as in ‘William the Conqueror,’ victor of the famed Battle of Hastings in 1066.”

1983: Prince Charles and Princess Diana tour Australia and New Zealand

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While the couple went on many royal tours overseas during their marriage, including to Italy, Thailand, South Korea and more, their 1983 voyage to Australia and New Zealand proved particularly significant in their relationship.

As was dramatized in season 4 of The Crown, Diana and Charles’ presence sparked a media frenzy that reportedly caused tension for the pair.

Diana later spoke about the tour during her 1995 BBC Panorama interview. “We’d be going around Australia, for instance, and all you could hear was, ‘Oh, she’s on the other side,’ ” she said. “Now, if you’re a man like my husband, a proud man, you mind about that if you hear it every day for four weeks.”

“You feel low about it, instead of feeling happy and sharing it,” she continued. “With the media attention came a lot of jealousy. A great deal of complicated situations arose because of that.”

February 14, 1984: Princess Diana and Prince Charles announce their second pregnancy

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On Valentine’s Day 1984, Buckingham Palace announced Diana’s second pregnancy.

“Both Prince Charles and Princess Diana are delighted by the news — as are the Queen, Prince Philip and all the members of both families,” Palace officials said.

September 15, 1984: Prince Charles and Princess Diana welcome their second baby

Diana Princess of Wales and Prince Charles with newborn Prince Harry. David Levenson/Getty

After nine hours of labor, Diana gave birth to the 6-pound, 14-ounce Prince Harry Charles Albert David, making him third in line for the throne. He arrived one week early and was delivered in the same room that William had been born in two years prior.

Charles appeared thrilled by the arrival, calling his new son “absolutely marvelous,” and telling a chanting crowd, “We have nearly got a full polo team now,” according to The New York Times.

In her 1992 biography, Diana revealed that Charles was disappointed that they had not had a girl. “First comment was: ‘Oh God, it’s a boy,’ second comment: ‘And he’s even got red hair,’ ” she recalled.

October 20, 1985: Prince Charles and Princess Diana give a joint interview

Princess Diana and Prince Charles. Georges De Keerle/Getty

In 1985, the couple sat down with ITN to debunk rumors about themselves and their relationship. Journalist Alastair Burnet asked if Diana had found it difficult to adapt to being a public figure.

“I did, yes, only because there was so much attention on me when I first arrived on the scene. … The pressure was enormous,” she said.

She denied trying to change anything about Charles, except for the “odd tie.”

He alluded to rows with Diana, telling Burnet, “I suspect most husbands and wives fight, they often have arguments.”

“But we don’t!” Diana interjected, to which he replied, “We occasionally do.”

1986: Prince Charles and Princess Diana reportedly begin having affairs

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Charles later confirmed in his authorized biography, The Prince of Wales, that he began his affair with Camilla in 1986.

Charles wrote letters that same year, later published in his biography, also pointing to his marital despair. “How awful incompatibility is, and how dreadfully destructive it can be for the players in this extraordinary drama,” he wrote, per AP News. “It has all the ingredients of a Greek tragedy … I never thought it would end up like this.”

Ex-army Major James Hewitt also claimed to have begun an affair with Diana around this time, which he said lasted for the next five years. Hewitt later attempted to sell their private letters from this time frame for $150,000.

Late 1987: Speculation of marriage trouble between Prince Charles and Princess Diana circulates

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In 1987, British tabloids began to run reports of a growing rift between the pair after they failed to attend Lady Amanda Ellingworth’s wedding and started spending time in separate locations.

According to the Los Angeles Times, a teacher’s aide at Harry’s school asked Diana whether her marriage was in trouble. The princess kept coy about her relationship status, replying, “It depends on what newspapers you read.”

July 29, 1991: Prince Charles and Princess Diana mark 10 years of marriage

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Despite reaching a major milestone in their marriage on their 10-year anniversary, there was little fanfare surrounding the event amid speculation that their relationship was on the rocks.

1992: Princess Diana talks of marriage trouble with Prince Charles in her tell-all

Prince Charles and Princess Diana. Tim Graham Photo Library via Getty

In 1992, Andrew Morton published Diana: Her True Story—in Her Own Words, for which Diana herself supplied recordings through her friend James Colthurst. The book addressed Diana’s unhappiness in her marriage, detailing issues she faced as a result, such as bulimia and suicide attempts.

​​”It rocked the royal family,” royal biographer Sally Bedell Smith said in PEOPLE and ABC’s The Story of Diana.

December 9, 1992: Prince Charles and Princess Diana separate

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In December 1992, Prime Minister John Major announced that Charles and Diana would be going their separate ways, also noting that their split would have “no constitutional implications.”

Per The Washington Post, Buckingham Palace also confirmed that there were no plans for the two to divorce at the time and that they would “from time to time attend family occasions and national events together.”

January 1993: Private calls between Prince Charles and Camilla Parker Bowles are released

In January 1993, British tabloids published a transcript of private calls that took place in 1989 between Charles and Camilla. In the calls, he said to her, “I fill up your tank” after she said that she couldn’t bear a Sunday night without him. The pair also said “I love you” several times.

June 29, 1994: Prince Charles admits to cheating on Princess Diana

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In an interview with ITN, Charles admitted he had committed adultery in his marriage to Diana, The New York Times reported. When asked if he had been faithful to her, he replied, “Yes … Until it became irretrievably broken down, us both having tried.”

October 1994: Prince Charles’ biography claims that his marriage to Princess Diana was loveless

In his 1994 biography, Charles claimed that his father had forced him into a loveless marriage with Diana. He stated that Philip convinced him that her reputation would otherwise suffer following a visit she made to Charles at the Queen’s Balmoral Castle.

Philip also insinuated that Diana was young enough “to be molded” into a future queen.

“The prince, in a state of emotional confusion, clung to these calculations,” the book read. “The pressures on him began to sweep him toward his destiny.”

September 6, 1995: Prince Charles and Princess Diana reunite for William’s first day of school

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In September 1995, Charles and Diana came together to send off Prince William on the young royal’s first day at Eton College.

October 18, 1995: Prince Charles and Camilla Parker Bowles attend a party sans Princess Diana

After years of keeping their love affair a secret and avoiding each other in public, Charles and Bowles attended a high-profile party, albeit with the prince arriving 90 minutes after her.

November 20, 1995: Princess Diana admits to cheating on Prince Charles

In an interview with BBC’s Panorama in November 1995, Diana spoke of the unhappiness she experienced in her marriage and confessed to having an extramarital affair, per the BBC.

When asked if she had been “unfaithful,” she replied, “Yes. I was in love with him. But I was very let down.”

Diana said the troubles she faced with Charles also affected her health. “[My eating disorder] was a symptom of what was going on in my marriage. I was crying out for help, but giving the wrong signals, and people were using my bulimia as a coat on a hanger,” she said. “They decided that was the problem: Diana was unstable.”

She continued, “The cause was the situation where my husband and I had to keep everything together because we didn’t want to disappoint the public, and yet obviously there was a lot of anxiety going on within our four walls.”

Diana also addressed Charles’ infidelities, telling host Martin Bashir, “Well, there were three of us in this marriage, so it was a bit crowded.”

February 28, 1996: Princess Diana agrees to divorce Prince Charles

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Diana announced in late February that she had agreed to her husband’s request for a divorce.

A representative for the princess issued the following statement: “The Princess of Wales has agreed to Prince Charles’s request for a divorce. The Princess will continue to be involved in all decisions relating to the children and will remain at Kensington Palace with offices in St. James’s Palace. The Princess of Wales will retain the title and be known as Diana, Princess of Wales.”

The Palace hinted there was more to consider, however, stating: “We can confirm that the Prince and Princess of Wales had a private meeting this afternoon at St. James’s Palace. At this meeting details of the divorce settlement and the Princess’s future role were not discussed. All the details on these matters, including titles, remain to be discussed and settled. This will take time.”

July 1996: Prince Charles and Princess Diana agree to divorce terms

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According to The Washington Post, Diana would lose the title of “Her Royal Highness” in the proceedings, but would still be known as Diana, Princess of Wales in future communication. The report also stated that she would receive a lump sum between $22 million and $27 million, as well as $600,000 per year to run her private office.

In addition, Diana would continue to live at Kensington Palace and share custody of the couple’s two sons.

August 28, 1996: Prince Charles and Princess Diana’s divorce is finalized

The former pair’s marriage was officially dissolved on Aug. 28, 1996, as stated in a divorce decree shared by CNN.

July 1997: Princess Diana begins dating Dodi Al Fayed following divorce from Prince Charles

By July 1997, Diana had seemingly started dating Egyptian film producer Dodi Al Fayed, the son of billionaire Harrods businessman Mohamed Al Fayed.

Though the pair had been acquaintances for years after Fayed’s polo team beat Charles’ in 1986, PEOPLE reported that their relationship did not turn romantic until nearly 10 years later, when Fayed invited the Princess of Wales and her two sons to vacation with him and his family in St-Tropez.

Diana later joined Fayed at a hotel in Paris before boarding a Harrods helicopter for a five-day Mediterranean cruise with the movie mogul.

Several London tabloids reported Charles as saying, “I’m happy if she’s happy” in response to the news of their romance.

August 31, 1997: Princess Diana dies, survived by ex-husband Prince Charles and their two sons

On Aug. 31, 1997, Princess Diana died at the age of 36 after going into cardiac arrest from massive internal injuries she sustained in a high-speed car crash.

Her boyfriend, Fayed, and the car’s driver, Henri Paul, were also killed in the accident.

CNN reported at the time that the car was traveling at 80 mph in a narrow tunnel along the Seine river, less than half a mile from the Eiffel Tower, when the driver lost control and slammed into a concrete post, then bounced into a wall. The group was reportedly being chased by members of the paparazzi on motorcycles.

Later reports, including from the BBC, indicated that the car was actually going 121 mph and that Paul had been legally drunk at the time of the incident.

September 6, 1997: Prince Charles attends Princess Diana’s funeral

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On Sept. 6, 1997, Charles attended his ex-wife’s funeral alongside their two sons, Prince William and Prince Harry. He broke royal protocol, which typically calls for military uniforms, by opting for a blue suit that Diana had reportedly favored on him.

“It was Diana’s favorite, blue suit, and she helped him choose it,” royal author Brian Hoey told PEOPLE. “She preferred him in blue [rather] than in black or gray. It was a lovely, silent compliment to her.”

In addition to the royal family, the event was attended by roughly 2,000 people, including Tom Cruise, Nicole Kidman, Sting, Mariah Carey, Tom Hanks, George Michael and Elton John, who performed his hit “Candle in the Wind” with lyrics that had been rewritten especially for Diana. More than 1 million people flooded the streets of central London to pay their respects, according to the BBC, and an estimated 2.5 billion viewers watched the event on TV.

August 2022: Princess Diana’s biographer says Prince Charles’ failed marriage to Diana “will always haunt him”

Twenty-five years after Princess Diana’s death, her biographer Andrew Morton spoke to PEOPLE about how the lasting legacy of Charles and Diana’s failed marriage lingers over the heir.

“His tragedy is whatever he does, whatever he says, however he behaves, he will be remembered for one thing: the fact that his fairy-tale marriage ended,” Morton explained.

He went on, “Just as Henry VIII is remembered for his six wives, Prince Charles is remembered for his first wife. It will always haunt him. His life has been defined by his marriage.”

Ingrid Seward, another royal biographer, added, “The ghost of Diana really stalked him at every turn.”

November 2023: The aftermath of Prince Charles and Princess Diana’s divorce is depicted in the final season of The Crown

Netflix’s historical drama The Crown is concluding with a sixth and final season, which spotlights how Charles and Diana’s relationship evolved after their divorce in 1996.

The first part of season 6 shows the former couple initially communicating about their children — Prince William and Prince Harry — but it opens up an opportunity to reach better terms with each other and exchange pleasantries.

“Even though we weren’t brilliant at being married, can we be brilliant at all this?” Diana says in an episode, played by actress Elizabeth Debicki.

“Diana and I are getting on rather well at the moment,” Charles says in another scene, portrayed by actor Dominic West.