The Most Awkward Moments from Princess Di and King Charles’ Engagement

By: Sam Watanuki | Published: Mar 19, 2024

In November 1977, an unexpected encounter laid the foundation for a royal romance. Prince Charles met young Lady Diana while he was dating her sister, Sarah. He later described Diana as a “jolly … attractive 16-year-old … full of life,” an innocent comment that, in hindsight, set an unusual tone for their future.

This meeting at Althorp House, though casual, marked the beginning of one of the most scrutinized relationships in royal history, foreshadowing the complexities that lay ahead.

Delayed Romance Ignites

Fast forward to 1980 — three years after their initial meeting, Charles finally made his move. The romance between Charles and Diana sparked quickly after years of minimal contact.

Prince Charles and Lady Diana Spencer pictured at the opening of the Mountbatten Exhibition

Source: Bettmann/Getty Images

Their courtship was remarkably brief, characterized by a few public outings and private visits. By this time, Diana was only 19, and the swift transition from acquaintance to fiancee in less than a year raised eyebrows as well as public interest.

The Proposal: Missing the Spark

In February 1981, within the grand walls of Buckingham Palace, Charles proposed to a young Diana. This critical moment, however, lacked the fairy-tale magic often associated with royal proposals, especially with Diana thinking it was a joke.

Princess Diana pictured wearing an outfit that matches the colors of Canada during a visit to Alberta

Source: Bettmann/Getty Images

Unlike the expected romantic grandeur, their engagement was a private affair, with no pomp or public spectacle, highlighting the private nature of their budding relationship yet contrasting sharply with the public’s expectations.

Public Announcement: A Formal Affair

On Feb. 24, 1981, the world awaited the official announcement with bated breath. When the engagement was formally declared, it was a moment of national pride, yet the announcement came across as a formal obligation rather than a declaration of love (via the BBC).

Prince Charles And Princess Diana On Their Last Official Trip Together - A Visit To The Republic Of Korea (south Korea).they Are Attending A Presidential Banquet At The Blue House In Seoul

Source: Tim Graham Photo Library via Getty Images

The event underscored the couple’s royal duty over personal sentiment, setting a tone of formality for their upcoming nuptials.

The Engagement Interview: 'Whatever Love Means'

Perhaps the most telling moment came during their engagement interview, when asked if they were in love, Diana quickly replied, “Of course,” only for Charles to add, “Whatever ‘in love’ means.”

A photo of Princess Diana sitting casually on steps outside a stone building. She is wearing a vibrant pink sweater and red and white gingham pants. Diana is resting her face in her hand

Source: Getty Images

This ambiguous comment became a defining moment, revealing a potential rift in their mutual understanding and casting a shadow over their romantic narrative.

Diana's Shock and Hurt

Diana laughed off the comment at the time, but she later admitted to being deeply affected by Charles’ words.

A black and white image of Princess Diana wearing a fascinator and smiling

Source: Getty Images

In personal recordings, she revealed that the remark “traumatized” her, highlighting the emotional distance between the couple even before they walked down the aisle (via Harper’s Bazaar).


Moving In: A Sudden Change

Following their engagement, Diana moved out of her Kensington apartment to Clarence House, marking a significant transition in her life.

Queen Elizabeth and Princess Diana. They are standing next to each other and are both wearing pearl necklaces.

Source: Global News/YouTube

This move, happening immediately after the proposal, underscored the rapid pace at which her life was transforming, thrusting her further into the public eye and royal responsibilities without the gradual adjustment usually afforded to newly engaged couples.


The Engagement Ring Controversy

The choice of engagement ring also sparked discussion. Diana selected a beautiful 12-carat sapphire ring, which, while stunning, was a catalog item and not bespoke, leading to debates about royal tradition versus personal choice.

A black and white image of Princess Diana at Accord Hospice.

Source: John MacInyre/Wikimedia Commons

This decision reflected Diana’s unique style but also hinted at the unconventional path their relationship would take.


Pre-Wedding Jitters Turn Serious

As the wedding approached, Diana’s doubts grew, culminating in her contemplating calling off the event. The pressure of the impending marriage and revelations about Charles’ past relationships left her feeling trapped and overwhelmed, a sentiment far removed from the fairy-tale romance the public imagined.

Prince Charles wearing a pinstriped suit and tie, is standing in front of a crowd. He is looking to the left with a serious expression, holding a flagpole with the United Kingdom's flag

Source: Wikimedia Commons

Charles, on the other hand, was also reported to have had pre-wedding doubts and considered calling off the wedding as well.


Sisters to the Rescue

In a moment of crisis, Diana’s sisters stepped in, reminding her of her commitment and the public’s expectations.

Princess Diana pictured in her wedding dress alongside her husband Prince Charles, 1981

Source: Terry Fincher/Princess Diana Archive/Getty Images

Their candid, if not stark, reminder reflected the irreversible step Diana was about to take, highlighting the blend of personal and public stakes involved in her decision to proceed with the marriage.


The Wedding: A Global Event with Private Doubts

On July 29, 1981, Charles and Diana’s wedding was watched by an estimated 750 million people worldwide.

Princess Di and Prince Charles in carriage on wedding day

Source: Anwar Hussein/Getty Images

Despite the public spectacle and grandeur, the event was clouded by private doubts and fears, illustrating the stark contrast between public perception and private reality.


Reflections on a Storybook Day

The royal wedding, while a moment of national celebration, was the beginning of a complex journey for Diana and Charles. Behind the scenes, the day was marked by personal anxieties and a sense of foreboding, setting the stage for a marriage that would face immense challenges and tragedy.

Princess Diana pictured seated alone at an event wearing a safari suit

Source: Tim Graham/Photo Library/Getty Images

This event was not just a union of two individuals but another chapter in the ongoing saga of the British royal family, remembered for its grandeur as well as its underlying tensions and awkwardness.