Did Henry VII try to remarry after his wife Elizabeth of York died?

Question

Did Henry VII try to remarry after his wife Elizabeth of York died?

Answer 1

After Elizabeth of York died in childbirth, Henry VII did later entertained vague thoughts of remarriage in order to renew the alliance with Spain - Juana, Dowager Queen of Naples (the niece of Ferdinand II of Aragon), Joanna, Queen of Castile (the daughter of Ferdinand and Isabella), and Margaret, Dowager Duchess of Savoy (the sister-in-law of Joanna of Castile) were all considered.

Not wishing the negotiations that had led to the marriage of his elder son to Catherine of Aragon to go to waste, he arranged a Papal dispensation for his younger son to marry his brother's widow — normally a degree of relationship that precluded marriage in the Roman Catholic Church. Also included in the dispensation was a proviso that would allow Henry VII himself to marry his widowed daughter-in-law.

Henry VII obtained the dispensation from Pope Julius II (1503–13) but had second thoughts about the value of the marriage and did not allow it to take place during his lifetime. Although he made half-hearted plans to re-marry and beget more heirs, these never came to anything. On his death in 1509, he was succeeded by his second son, Henry VIII.

Answer 2

Yes.  After Katherine of Aragon's sister Juana's husband Philip the Handsome died, and she went crazy, he approached her father Ferdinand of Aragon for her hand in marriage, crazy and all.  He didn't believe she was that crazy and wanted her for breeding purposes and for control of Castile.  Of course Ferdinand wasn't going to give permission and give up his own control of Castile, as regent for his nephew Charles VI.  It's hard to say if he was serious or not, or just doing some political jostling,  He had met Juana and was take with her good looks.