So this example counts, since the king of Portugal was the second husband of a woman. Later on, after his wife's death in childbirth, he remarried with one of her sisters, Infanta Maria.
Infanta Isabel married 1st Prince D.Afonso, only son of King D.João II and Queen D.Leonor
When the Prince died after a horse fall his widow returned to Castille.
When King D.Manuel succeeded his cousin and brother-in-law (he was Q.Leonor's brother), the Catholic Kings offered him the hand of their 3rd daughter Infanta Maria, but D.Manuel insisted on marrying Pss Isabel whom he already met and had feelings for.
The rest is history. The two got married, Isabel died in childbirth and D.Manuel eventually married Maria, whom he had rejected previously.
Speaking of 2nd husbands, when Queen D.Maria suddenly died, D.Manuel married 3rd Infanta D.Leonor of Austria, Charles V's sister, who had been engaged to D.Manuel's son, the future D.João III.
Confused, it gets worse .
When D.Manuel died, despite the interest of D.João to marry his step-mother, Charles V blocked the idea and married his sister to King François I of France, so Leonor was twice a Queen , though not a very fortunate one in either country.
Still in Portugal King D.Pedro II was the 2nd husband of his sister-in-law Queen Maria Francisca Isabel of Savoy-Nemours, who had been married to his brother, King D.Afonso VI, and who was deprived from crown and wife by younger brother.
In medieval times the two brothers D.Sancho II and D.Afonso III married widows - Mécia Lopes de Haro, the first, and Mathilde, countess of Boulogne, the second.
D.Fernando I's wife, Leonor Telles, had her marriage annulled in order to marry the king.
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