Several women were lined up as possible brides for Albert Victor.
The first, in 1889, was his cousin Princess Alix of Hesse and by Rhine, but she did not return his affections and refused his offer of engagement.
She would later marry Tsar Nicholas II of Russia, another of Albert Victor's cousins, in 1894.
The second, in 1890, was a love match with Princess Hélène of Orléans, a daughter of Prince Philippe, Count of Paris, a pretender to the French throne who was living in England after being banished from France in 1886.

At first, Queen Victoria opposed any engagement because Hélène was Roman Catholic.
Victoria wrote to her grandson suggesting another of her grandchildren, Princess Margaret of Prussia, as a suitable alternative, but nothing came of her suggestion, and once Albert Victor and Hélène confided their love to her, the Queen relented and supported the proposed marriage.
Hélène offered to convert to the Church of England, and Albert Victor offered to renounce his succession rights to marry her.
To the couple's disappointment, her father refused to countenance the marriage and was adamant she could not convert.
Hélène travelled personally to intercede with Pope Leo XIII, but he confirmed her father's verdict, and the courtship ended.
She later became the Duchess of Aosta.

In mid-1890, Albert Victor was attended by several doctors.
In Albert Victor's and other correspondence, his illness is only referred to as "fever" or "gout".
Some biographers have assumed he was suffering from "a mild form of venereal disease", perhaps gonorrhea, which he may have suffered from on an earlier occasion, but the exact nature of his illness is unknown.

In late 1891, the Prince was implicated as having been involved with a former Gaiety Theatre chorus girl, Lydia Miller (stage name Lydia Manton), who committed suicide by drinking carbolic acid.
Although she was the nominal mistress of Lord Charles Montagu, who gave evidence at the inquest, it was alleged that he was merely a cover for the Prince, who had requested she give up her theatrical career on his behalf, and that the authorities sought to suppress the case by making the inquest private and refusing access to the depositions.
Similarly to the Cleveland Street scandal, only overseas newspapers printed Albert Victor's name, but regional British newspapers did quote the radical London newspaper The Star which published: "It is a fact so well known that the blind denials of it given in some quarters are childishly futile.
Lydia Manton was the petite amie of a certain young prince, and that, too, quite recently."
It was labelled "a scandal of the first magnitude ... on the lips of every clubman", and compared to the Tranby Croft affair, in which his father was called to give evidence at a trial for slander.

Rumours also surfaced in 1900, after Albert Victor's death, of his association with another former Gaiety girl, Maude Richardson (birth name: Louisa Lancey), and that the royal family had attempted to pay her off.
In 2002, letters purported to have been sent by Albert Victor to his solicitor referring to a payoff made to Richardson of £200 were sold at Bonhams auction house in London.
Owing to discrepancies in the dates and spelling of the letters, one historian has suggested they could be forgeries.

In 1891, Albert Victor wrote to Lady Sybil St Clair Erskine that he was in love once again, though he does not say with whom, but by this time another potential bride, Princess Mary of Teck, was under consideration.
Mary was the daughter of Queen Victoria's first cousin Princess Mary Adelaide, Duchess of Teck.
Queen Victoria was very supportive, considering Mary ideal—charming, sensible and pretty.
On 3 December 1891 Albert Victor, to Mary's "great surprise", proposed to her at Luton Hoo, the country residence of the Danish ambassador to Britain.
The wedding was set for 27 February 1892.
Several women were lined up as possible brides for Albert Victor. The first, in 1889, was his cousin Princess Alix of Hesse and by Rhine, but she did not return his affections and refused his offer of engagement. She would later marry Tsar Nicholas II of Russia, another of Albert Victor's cousins, in 1894. The second, in 1890, was a love match with Princess Hélène of Orléans, a daughter of Prince Philippe, Count of Paris, a pretender to the French throne who was living in England after being banished from France in 1886.
At first, Queen Victoria opposed any engagement because Hélène was Roman Catholic. Victoria wrote to her grandson suggesting another of her grandchildren, Princess Margaret of Prussia, as a suitable alternative, but nothing came of her suggestion, and once Albert Victor and Hélène confided their love to her, the Queen relented and supported the proposed marriage. Hélène offered to convert to the Church of England, and Albert Victor offered to renounce his succession rights to marry her. To the couple's disappointment, her father refused to countenance the marriage and was adamant she could not convert. Hélène travelled personally to intercede with Pope Leo XIII, but he confirmed her father's verdict, and the courtship ended. She later became the Duchess of Aosta.
In mid-1890, Albert Victor was attended by several doctors. In Albert Victor's and other correspondence, his illness is only referred to as "fever" or "gout". Some biographers have assumed he was suffering from "a mild form of venereal disease", perhaps gonorrhea, which he may have suffered from on an earlier occasion, but the exact nature of his illness is unknown.
In late 1891, the Prince was implicated as having been involved with a former Gaiety Theatre chorus girl, Lydia Miller (stage name Lydia Manton), who committed suicide by drinking carbolic acid. Although she was the nominal mistress of Lord Charles Montagu, who gave evidence at the inquest, it was alleged that he was merely a cover for the Prince, who had requested she give up her theatrical career on his behalf, and that the authorities sought to suppress the case by making the inquest private and refusing access to the depositions. Similarly to the Cleveland Street scandal, only overseas newspapers printed Albert Victor's name, but regional British newspapers did quote the radical London newspaper The Star which published: "It is a fact so well known that the blind denials of it given in some quarters are childishly futile. Lydia Manton was the petite amie of a certain young prince, and that, too, quite recently." It was labelled "a scandal of the first magnitude ... on the lips of every clubman", and compared to the Tranby Croft affair, in which his father was called to give evidence at a trial for slander.
Rumours also surfaced in 1900, after Albert Victor's death, of his association with another former Gaiety girl, Maude Richardson (birth name: Louisa Lancey), and that the royal family had attempted to pay her off. In 2002, letters purported to have been sent by Albert Victor to his solicitor referring to a payoff made to Richardson of £200 were sold at Bonhams auction house in London. Owing to discrepancies in the dates and spelling of the letters, one historian has suggested they could be forgeries.
In 1891, Albert Victor wrote to Lady Sybil St Clair Erskine that he was in love once again, though he does not say with whom, but by this time another potential bride, Princess Mary of Teck, was under consideration. Mary was the daughter of Queen Victoria's first cousin Princess Mary Adelaide, Duchess of Teck. Queen Victoria was very supportive, considering Mary ideal—charming, sensible and pretty. On 3 December 1891 Albert Victor, to Mary's "great surprise", proposed to her at Luton Hoo, the country residence of the Danish ambassador to Britain. The wedding was set for 27 February 1892.
Prince Albert Victor, Duke of Clarence and Avondale