Royal engagements are often highly anticipated events that captivate the public’s imagination. The announcement of a royal engagement typically brings excitement, celebrations, and, of course, the unveiling of the engagement ring. However, throughout history, some royal engagements have sparked intense controversy, shaking the foundations of monarchy and social norms. Whether due to personal scandals, political implications, or clashes with tradition, these engagements have left a lasting mark on royal history. Here are some of the most controversial royal engagements of all time.

One of the earliest and most significant controversial royal engagements in modern history was that of King Edward VIII and Wallis Simpson. In 1936, King Edward VIII, the British monarch, announced his engagement to Wallis Simpson, an American divorcée. This engagement caused a scandal because Simpson had been divorced twice, and the Church of England, of which Edward was the Supreme Governor, forbade the remarriage of divorced people if their former spouses were still alive. Faced with immense pressure from both the British government and the Church, Edward chose to abdicate the throne in order to marry Simpson, leading to one of the most dramatic moments in British royal history. Edward became the Duke of Windsor, and his marriage to Wallis Simpson, while ultimately sanctioned by the Church of England, was controversial and marked by public disapproval.

Another controversial royal engagement occurred in 1981 when Prince Charles, the heir to the British throne, became engaged to Lady Diana Spencer. While the engagement itself was not initially controversial, the marriage that followed soon became the focus of intense media scrutiny. The 1980s media frenzy surrounding Charles and Diana’s wedding was unlike anything seen before, but their engagement was clouded by rumors of Charles’ prior relationships and his reportedly indifferent feelings toward Diana. Many questioned whether the two were truly in love or if the marriage was a political arrangement to shore up the royal family’s public image. Their relationship was marred by infidelity and a very public divorce in 1996, making the engagement itself a symbol of a troubled royal union.

The engagement of Princess Margaret, Queen Elizabeth II’s younger sister, to Peter Townsend in the 1950s was another controversial royal moment. Peter Townsend, a divorced man, was deemed unsuitable as a husband for a royal princess by the Church of England, which influenced the monarchy’s decision. Despite their clear affection for each other, Princess Margaret was forced to end her engagement to Townsend in 1955, as her sister, Queen Elizabeth II, and the British government did not approve of the marriage. This event led to public debates about love versus duty, and the role of the monarchy in personal relationships, with many feeling that Margaret’s romantic choices were being unjustly constrained by the institution.

In more recent history, the engagement of Prince Harry to Meghan Markle in 2017 raised eyebrows and triggered a series of controversies. Meghan, a divorced American actress, was not the typical royal bride, and her engagement to Prince Harry challenged royal traditions in several ways. The couple’s decision to step back from royal duties in 2020 only intensified the controversy surrounding their engagement, as the media and the royal family grappled with the implications of their choice to prioritize personal happiness over royal obligations. Meghan’s outspoken nature, paired with public criticisms of the royal family, made this engagement one of the most talked-about and divisive in modern royal history.

Lastly, the engagement of Queen Victoria’s eldest son, the Prince of Wales (later Edward VII), to Princess Alexandra of Denmark in 1862 also faced significant backlash. Their union was initially contentious because of the Prince of Wales’ reputation as a womanizer. His affairs were widely known, and many were skeptical about his ability to be a faithful husband. However, the engagement to Princess Alexandra proved to be successful, as their marriage became a cornerstone of the royal family. Yet, it was always under the shadow of the Prince’s prior scandals, which continued to haunt him throughout his life.

Royal engagements have always been more than just personal commitments—they are political, social, and cultural events that shape public perception of the monarchy. The most controversial royal engagements, from Edward VIII’s abdication to the modern-day struggles of Prince Harry and Meghan Markle, serve as reminders of the immense pressures placed on royal figures and their relationships. These engagements not only shaped royal history but also sparked important conversations about love, duty, and the evolving role of the monarchy in contemporary society.