Though neither proposal is shown in The Crown, Prince Charles proposed to two other women before proposing to Diana. The Crown, season 3 explored the Prince of Wales’ early relationship with Camilla Shand, though Charles didn't propose to Camilla — now his wife and the Duchess of Cornwall — until 2005. Season 4 showed the continuation of Charles and Camilla's relationship as well as Charles' introduction, engagement, and marriage to Lady Diana Spencer. In The Crown, season 4, episode 2, “The Balmoral Test,” Charles officially begins dating Diana, and at the end of episode 3, “Fairytale,” they are wed. By the finale, “War,” Charles has begun an affair with Camilla — a factor that contributes in no small part to the breakdown of his marriage with Diana.
Despite the fact that Charles is known to have proposed to at least two women before proposing to Diana, these short-lived relationships are obviously of less public interest than his tumultuous marriage with Diana and scandalous affair with Camilla. Diana became so famous and Camilla so infamous that nearly forty years later they are still regular subjects of tabloid gossip. In real life, Camilla and Diana are the two most significant and highly-publicized romantic relationships that Prince Charles had, so it’s no surprise that the global fascination with Camilla and Diana would be reflected in The Crown. But it’s interesting that the two women who rejected Charles were apparently aware of the factors that led to Charles’ affair with Camilla and divorce from Diana, seeming to foreshadow the major plot points in The Crown, season 4.
Just before dating Diana and while in an on-again-off-again relationship with Camilla, Charles made two proposals to Anna Wallace and one proposal to Lady Amanda Knatchbull. Scottish heiress Anna Wallace — a.k.a. “Whiplash Wallace” — turned Charles down for the simple reason that she would not settle for playing second-fiddle to Camilla, with whom Charles was continually obsessed. On the other hand, Lady Amanda Knatchbull rejected Charles for a slightly different reason. Amanda was Charles’ second cousin through his great uncle and her grandfather, Lord Mountbatten. When Lord Mountbatten was assassinated by the IRA in 1979, Amanda also lost her grandmother and younger brother. Charles proposed soon after Lord Mountbatten’s death and the grieving young woman simply did not want the scrutiny of being in the royal family, especially at a time when she felt her most vulnerable.
These proposals — and subsequent rejections — occurred in the same year. In 1980, Charles was a desperate bachelor of 32-years and keen on selecting a suitable companion with whom to produce an heir. Likely combined with the fact that he was grieving the death of his great-uncle and close friend, Lord Mountbatten, Charles made the proposals in quick succession, proposing to both Lady Amanda Knatchbull and Anna Wallace in 1980. After Charles finally made a successful proposal to Diana in February of the following year, the royal couple's fairytale wedding took place just 5 months later on July 29, 1981.
Charles' failed proposals are largely unknown because, unlike Camilla, who was considered unsuitable from the beginning, Lady Amanda Knatchbull was not objectionable to the press or royal family. And unlike Diana, who became so adored that she overshadowed Charles, Anna Wallace's relationship with Charles was over almost as soon as it had begun. Anna Wallace and Amanda Knatchbull will likely remain footnotes in the life of Prince Charles because neither woman became loved or hated enough to be the subject of tabloid gossip for decades, let alone featured in a big-budget Netflix drama like The Crown – and they probably wouldn’t have it any other way.