• King Charles III romanced over two dozen women before his marriage.
• Many of the women King Charles was involved with were aware of his thoughts and feelings towards Camilla Parker Bowles.
• One of the King’s less talked-about love interests had a tragic fall from the window and died months after Princess Diana.

King Charles III, a figure whose romantic history has been as scrutinized as his public life, navigated a complex path through personal relationships before assuming the British throne. In a journey marked by both passion and discretion, the then-Prince Charles was said to have romanced over two dozen women.

The question of whether King Charles saw each of these women as “The One” or if they saw themselves in that light remains obscured by discretion and the passage of time. Central to the King’s romantic narrative was the ever-present thought of Camilla Parker Bowles, a reality many of his companions were acutely aware of. This included Princess Diana, whose fairy tale marriage with the King was watched by the world.

The women in King Charles’ life had varied reactions to his relationship with Queen Camilla; some ignored it, others hoped for a change, and a few were simply curious about the relationship’s trajectory. Despite their initial intentions, most of these women found relief when the prince’s persistent late-night calls—a hallmark of his courtship—finally ceased. Here’s a look inside the British monarch’s personal relationships through the years.

Lady Sarah Spencer

Before the world was captivated by the fairy tale union between King Charles and Princess Diana, the former engaged in a less-publicized, on-again, off-again courtship with Princess Diana’s older sister, Lady Sarah Spencer. This relationship, marked by its fluctuating nature, eventually foundered in King Charles’ perception of Lady Sarah as “too flighty.”

Despite the proposal and a shared holiday on Eleuthera, Ellingworth was not committed to the idea of marriage and declined.

Anna Wallace

King Charles III’s romantic entanglements before his marriage to Princess Diana included a significant relationship with Anna Wallace. Daughter of Scottish landowner Hamish Wallace, Wallace was the King’s last significant relationship before his engagement to Princess Diana. Interestingly, King Charles had proposed marriage to Wallace not once but twice, highlighting the seriousness of their courtship at one point.

However, the relationship was fraught with obstacles, including mutual external romantic interests, which ultimately made their union untenable. Their relationship reached its conclusion at a polo ball in 1980, an event marked by the King’s inattention towards Wallace as he chose to dance all night with Camilla.

Jane Wellesley

Between 1973 and 1974, King Charles was romantically involved with Jane Wellesley, daughter of the 8th Duke of Wellington. With her striking looks and distinguished lineage, Wellesley was widely regarded as a leading contender for marriage to the King. Despite the end of their relationship, Wellesley carved out a successful career for herself as a filmmaker and biographer and remained unmarried.

Lady Amanda Ellingworth

In 1980, King Charles proposed to Lady Amanda Ellingworth, his second cousin and granddaughter of Earl Mountbatten, marking a notable moment in his quest for a partner as he reached his self-imposed marriage deadline.

Despite the proposal and a shared holiday on Eleuthera, Ellingworth was not committed to the idea of marriage and declined. Notably, King Charles had earlier broached the subject of marrying Ellingworth with her mother in 1974, when she was only 17, without her direct knowledge.

Lady Dale Tryon

The King’s romantic entanglements also involve his connection to Lady Dale Tryon, who played a significant, though less reported, role in his life. Lady Dale, once described as “the only woman who ever understood Charles,” was a prominent socialite and a successful businesswoman in the fashion industry.

Lady Dale met the King through her husband, Anthony Tryon, 3rd Baron Tryon, becoming entwined in a supposed love triangle with Charles and Camilla during the 1970s and 1980s. Despite the King’s ongoing affair with Camilla, Lady Dale captured his attention, earning the affectionate nickname “Kanga” from him.

Their relationship was so close that when Lady Dale gave birth to a son, she named him after the then-Prince and made him the godfather. Lady Dale’s involvement with Charles extended beyond personal ties; she leveraged her association with him to gain publicity for her fashion line, cleverly named “Kanga.”

She also became a friend to Princess Diana and an adversary to Queen Camilla, even seeing Diana wear one of her designs in 1985. Tragically, Lady Dale’s life was fraught with health challenges, including a battle with Perthes’ disease and uterine cancer.

Her struggle intensified in 1996 after becoming addicted to painkillers, leading to a tragic incident where she fell nearly eight meters from a window. This accident resulted in her paralysis from the waist down, a dire outcome that fueled speculation and controversy. Some believed she was pushed, while others thought she might have jumped.

Amidst swirling rumors and personal turmoil, Tryon’s marriage dissolved, and her mental health suffered, leading to her being sectioned under the Mental Health Act. Despite these challenges, her love for the then-Prince persisted. She was reportedly seen attempting to engage with him at a polo match in 1997, an effort met with distance from King Charles, who stated they were no longer close friends.

King Charles’ ex-mistress’s life came to a sorrowful end in November 1997 when she died of septicemia, just months after Princess Diana’s tragic death in a Paris car crash, at the age of 49. Her story resurfaced over the years, though the Tryon family has consistently denied the claims of an affair.