In 1881, King Kalākaua tried to arrange a marriage between Kaʻiulani and Japan's Prince Higashifushimi Yorihito in hopes of creating an alliance between Japan and the Kingdom of Hawaii. However, the prince declined, as he was already pre-arranged to marry a Japanese noble lady, Arima Yoriko. In 1894, Queen Liliuokalani wrote to her niece to marry one of the three: Prince David Kawānanakoa, Prince Jonah Kūhiō Kalanianaʻole, or Prince Komatsu Akihito (then studying in London), the half-brother of Higashifushimi Yorihito. She replied to her aunt that she would prefer to marry for love unless it was necessary to protect the independence of the Hawaiian Kingdom. On February 3, 1898, she declared her engagement to Prince David Kawānanakoa, but her early death ended the hope of marriage.