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The twice widowed Fitzherbert soon entered London high society. In spring, 1784, she was introduced to a youthful admirer: George, Prince of Wales, six years her junior. The prince became infatuated with her and pursued her endlessly until she agreed to marry him. Secretly, and – as both parties were well aware – against the law, they went through a form of marriage on 15 December 1785, in the drawing room of her house in Park Street, London. Her uncle, Henry Errington, and her brother, Jack Smythe, were the witnesses. This invalid marriage ceremony was performed by one of the prince's Chaplains in Ordinary, the Reverend Robert Burt, whose debts (of £500) were paid by the prince to release him from the Fleet Prison.
The marriage was not valid because it had not received the prior approval of King George III and the Privy Council as required by the Royal Marriages Act 1772. Had approval been sought, it might not have been granted for many reasons including, for example, Fitzherbert's Roman Catholic allegiance. Had consent been given and the marriage been legal, the Prince of Wales would have been automatically removed from the succession to the British throne under the provisions of the Bill of Rights and the Act of Settlement 1701. His brother, Prince Augustus Frederick, contracted an invalid marriage with Lady Augusta Murray in 1793 without the King's consent and had two children with her.
On 23 June 1794, Fitzherbert was informed by letter that her relationship with the Prince was over. George told his younger brother, Prince Frederick, Duke of York and Albany, that he and Fitzherbert were "parted, but parted amicably", conveying his intention to marry their first cousin, Duchess Caroline of Brunswick. According to King George III it was the only way out of a hole: his heir apparent's debts of £600,000 would be paid the day he wed. So the Prince married Caroline on 8 April 1795. In 1796, three days after Caroline gave birth to their daughter, Princess Charlotte of Wales, on 10 January, the Prince of Wales wrote his last will and testament, bequeathing all his "worldly property . . . to my Maria Fitzherbert, my wife, the wife of my heart and soul". Although by the laws of the country she "could not avail herself publicly of that name, still such she is in the eyes of Heaven, was, is, and ever will be such in mine...". However, this did not lead to a reunion. The Prince finally sought a reconciliation with his "second self" during the summer of 1798. By then, he had separated from Caroline for good and was bored with his mistress, Frances Villiers, Countess of Jersey. They reconciled again after the Pope deemed their marriage legitimate.
During the first few years of his reign as King George IV, he turned violently against Fitzherbert and several of his former associates. Whenever he mentioned her name it was "with feelings of disgust and horror", claiming that their union "was an artificial marriage... just to satisfy her; that it was no marriage – for there could be none without a licence or some written document." Fitzherbert was in possession of documents and after their final break her demands for her annuity payments were often accompanied by veiled threats to go public with her papers if she did not receive the funds. In June 1830, when the King was dying, he eagerly seized her "get well soon" letter and, after reading it, placed it under his pillow. Fitzherbert – who had no idea just how ill he was – was deeply hurt that he had never replied to her final letter. However, before dying, the King asked to be buried with Fitzherbert's eye miniature around his neck, which was done.