Going "against friends' advice and common custom", within thirty days More had married one of the many eligible women among his wide circle of friends. He chose the rich widow Alice Middleton as his second wife, having met her while working with her late husband who had been a prosperous merchant. The speed of the marriage was so unusual that More had to get a dispensation of the banns, which due to his good public reputation he easily obtained. Alice More lacked Jane's docility; More's friend Andrew Ammonius derided Alice as a "hook-nosed harpy." Erasmus, however, called their marriage happy. More had no children from his second marriage, although he raised Alice's daughter from her previous marriage as his own. More also became the guardian of a young girl named Anne Cresacre, who would eventually marry his son, John More. An affectionate father, More wrote letters to his children whenever he was away on legal or government business, and encouraged them to write to him often.
More insisted upon giving his daughters the same classical education as his son, a highly unusual attitude at the time.[10]:146–47 His eldest daughter, Margaret, attracted much admiration for her erudition, especially her fluency in Greek and Latin. More told his daughter of his pride in her academic accomplishment in September 1522, after he showed the Bishop a letter she had written:
When he saw from the signature that it was the letter of a lady, his surprise led him to read it more eagerly ... he said he would never have believed it to be your work unless I had assured him of the fact, and he began to praise it in the highest terms ... for its pure Latinity, its correctness, its erudition, and its expressions of tender affection. He took out at once from his pocket a portague [A Portuguese gold coin] ... to send to you as a pledge and token of his good will towards you.
More's decision to educate his daughters set an example for other noble families. Even Erasmus became much more favourable once he witnessed their accomplishments.