Prince Charles is the longest-serving Prince of Wales in history, thanks to his mother Queen Elizabeth II's decades-long reign. The British royal family is always surrounded by gossip, scandal, and an insane amount of press — from Charles's sister Anne's attempted kidnapping, to his rebellious brother Andrew's antics, Charles's generation of Windsors has been on the front page of the press quite often.
Charles, who was born to Queen Elizabeth II and Prince Phillip, Duke of Edinburgh, in 1948, has had his fair share of media scandal as well. He had numerous rendezvous before settling down with Diana Spencer, but he continued to have one notable affair, with Camilla Parker Bowles. Charles's affair with (and eventual marriage to) Camilla rocked the royal family, and nearly destroyed it in a very similar way his great uncle, Edward VIII, did when he abdicated the throne to marry Wallis Simpson.
Only two generations before Charles was dubbed Prince of Wales, a scandal shook the British monarchy when King Edward VIII (Charles's great uncle) famously abdicated his throne a year into his reign to marry the woman he loved, an American divorcee named Wallis Simpson. The Windsor dynasty was nearly ruined by the former king's decision, and was therefore determined to prevent any such action in the future.
However, a young Charles became curious about his exiled uncle, and went to meet him in Paris, where he found that Edward was happy and still beloved by most of Britain. This didn't bode well for the royal family, who wanted to prevent Charles from following in the footsteps of the ruined Edward VIII.
Instead of seeing his uncle as a warning, though, Charles saw him as an object of sympathy and affection, someone who followed his heart and still kept that of the British people.
Prince Charles's romance with Princess Diana – Diana Spencer when they were dating – is most notorious for his affair with long-time love Camilla Parker-Bowles, but the royal couple's courtship didn't begin on the most average terms, either. The pair was introduced by Diana's older sister, whom Charles had actually been seeing at the time.
Charles met Diana in 1977, when she was only 16. After he ended his relationship with her sister, Sarah, he began courting Diana in 1980. Remarkably, the sisters never let their relationships with the prince stand in the way of their own relationship, and Sarah even considered herself "cupid" for introducing them.
Lord Mountbatten took it upon himself to mold a young Prince Charles into a future king — part of this involved securing the prince the perfect wife. In a 1974 letter to Charles, Mountbatten encouraged Charles to have as many affairs as he could before settling into marriage — it was thanks to this advice that Charles took up with Camilla Shand, thus beginning a decades-long affair.
Mountbatten was not shy about his own ambitions, and around the same time, he began grooming Charles for marriage, he also tried to arrange a courtship between Charles and his cousin Amanda, Mountbatten's granddaughter. Charles, loyal to his advisor and great uncle, wrote to Amanda's mother, who politely declined the prince's offer of courtship.
Lord Mountbatten's influence over Charles was pertinent to the young prince's development. Charles was never close with his father, and Mountbatten was around at the pinnacle of Charles's prince-hood, just as the young man was about to venture out into society. It seemed Mountbatten's advice to Charles, that the prince date as much as he could before settling down with a respectable wife, struck a chord, and Charles became a media darling for the amount of press he attracted thanks to his dating life.
Charles supposedly dated around 20 women before settling down with Diana Spencer, although the press would have a field day any time the prince so much as looked at a young woman. This meant a lot of rumors about the prince's love life — some even believe he had an affair with Barbara Streisand.