In 1579, arrangements began to be made for marrying him to Elizabeth I of England. Alençon, now Duke of Anjou, was in fact the only one of Elizabeth's foreign suitors to court her in person. He was 24 and Elizabeth was 46. Despite the age gap, the two soon became very close, Elizabeth dubbing him her "frog" on account of a frog-shaped earring he had given her. Whether or not Elizabeth truly planned marrying Anjou is a hotly debated topic. It is obvious that she was quite fond of him, knowing that he was probably going to be her last suitor. There are many anecdotes about their flirting. The match was controversial in the English public: English Protestants warned the Queen that the "hearts [of the English people] will be galled when they shall see you take to husband a Frenchman, and a Papist ... the very common people well know this: that he is the son of the Jezebel of our age", referring to the Duke's mother, Catherine de' Medici. Of her Privy Council, only William Cecil, Lord Burghley, and Thomas Radclyffe, 3rd Earl of Sussex, supported the marriage scheme wholeheartedly. Most notable councillors, foremost among them Robert Dudley, 1st Earl of Leicester, and Sir Francis Walsingham, were strongly opposed, even warning the Queen of the hazards of childbirth at her age.
Between 1578 and 1581, the Queen resurrected attempts to negotiate a marriage with the Duke of Alençon, who had put himself forward as a protector of the Huguenots and a potential leader of the Dutch. In these years Walsingham became friends with the diplomat of Henry of Navarre in England, the anti-monarchist Philippe de Mornay. Walsingham was sent to France in mid-1581 to discuss an Anglo-French alliance, but the French wanted the marriage agreed first, and Walsingham was under instruction to obtain a treaty before committing to the marriage. He returned to England without an agreement. Personally, Walsingham opposed the marriage, perhaps to the point of encouraging public opposition. Alençon was a Catholic, and as his elder brother, Henry III, was childless, he was heir to the French throne. Elizabeth was past the age of childbearing, and had no clear successor. If she died while married to the French heir, her realms could fall under French control. By comparing the match of Elizabeth and Alençon with the match of the Protestant Henry of Navarre and the Catholic Margaret of Valois, which occurred in the week before the St. Bartholomew's Day massacre, the "most horrible spectacle" he had ever witnessed, Walsingham raised the spectre of religious riots in England in the event of the marriage proceeding. Elizabeth put up with his blunt, often unwelcome, advice, and acknowledged his strong beliefs in a letter, in which she called him "her Moor [who] cannot change his colour".
At last, Elizabeth pragmatically did not judge the union a wise one, considering the overwhelming opposition of her advisors. She continued, however, to play the engagement game, if only to warn Philip II of Spain what she might do, if it became necessary. Finally, the game played itself out, and Elizabeth bade her "frog" farewell in 1581. On his departure she penned a poem, "On Monsieur's Departure", which, taken at face value, has lent credence to the notion that she may really have been prepared to go through with the match.