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Christina of Milan
Though the great-niece of Henry's first wife, Catherine of Aragon, 16-year-old Christina of Milan presented a very attractive bridal option for the middle-aged Henry VIII. Christina was niece to the powerful Holy Roman Emperor Charles V and reported to be "an excellent beauty." The portrait painted of Christina by Tudor court painter Hans Holbein fired the middle-aged monarch's imagination.
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He sent an envoy to visit Christina at the court of her aunt, Mary of Hungary, Regent of the Netherlands, in Brussels. There, the teenaged princess reportedly left little doubt as to views on Henry VIII. She would only marry Henry VIII, Christina reportedly said, if she had two heads. Ironically, in 1541 Christina would instead marry Anne of Cleves' ex-fiancè, Francis of Lorraine.
Marie de Guise
When Marie de Guise received word of Henry VIII's interest, her response was swift: she got engaged to someone else. Her choice? Henry's nephew, James V of Scotland. A curvy widow of 22, Marie was related to the French royal house of Valois and had already had two sons. But even as the wife of James V, Marie de Guise would yet exercise influence over the Tudor dynasty. Her daughter, Mary, Queen of Scots, would later pose one of the more formidable challenges to the rule of Henry VIII's daughter, Elizabeth I, and pay for it with her head.
Role as Queen 
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