1. Royals whose bride ended up marrying his father.
2. Royals who were older than their step-mother.
Case # 1: Eleonor of Habsburg, daughter of Joan the Mad was bethroted to the Crown-Prince D.Jo„o of Portugal, future D.Jo„o III, 4 years younger.
Meanwhile D.Jo„o's mother, D.Maria (Eleonor's aunt) died and his father, D.Manuel, took Eleonor as his 3rd wife to the dispair and anger of the prince.
When D.Manuel died, shortly 3 years after his last wedding, D.Jo„o wanted to marry his step-mother to whom he was secretely in love.
Eleonore's brother, Emperor Carlos V refused, and the young widow was unfortunately bethroted to the king of France Francis I.
D.Jo„o eventually married Eleonore's younger sister, Catarina of Habsburg, youngest daughter of Joan the Mad with whom she shared the internment in Tordesillas.
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