Masako began an on-off courtship with the crown princess after she was introduced to him at a palace party in 1986
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"It was in the autumn of 1986 that the young diplomat, accompanied by her parents, met Crown Prince Naruhito at a palace party in honour of the Infanta Elena of Spain. Legend has it that more than three dozen potential companions for the crown prince were invited to the party, a list of their names being given to the royal heir in advance. Apparently, Masako was added at the last minute, her name handwritten by someone in the Imperial Household Agency.
The crown prince was instantly enamoured of Masako and began to pursue her. This despite objections from his advisers, who believed she was an inappropriate choice in light of a relative's involvement with a chemical company which had once caused an environmental disaster. Naruhito was undeterred, and determined to make Masako his wife.
Years later, in 2002, she would recall: "I never even in my dreams thought that one day I would enter the Imperial Family." And it seems Masako, who had just passed the Foreign Ministry exam when she crossed paths with her future husband, almost didnít.