Geoffrey Chaucer was a squire and diplomat of the king. His "Tales of the Canterbury Pilgrims" portrayed characters of every social class, including the knight with his squire, abbot, prioress, nun, priest, monk, friar, poor parson of the country, summoner (who enforced the jurisdiction and levied the dues of the church courts), pardoner (sold pardons from the pope), scholar, attorney, doctor, merchant, sailor, franklin, yeoman, haberdasher, tapestry- maker, ploughman, cook, weaver, dyer, upholsterer, miller, reeve, carpenter. There were Chaucer stories about a beautiful and virtuous wife disliked by her mother-in-law, the difficulty of marriage between people of different religions, the hatred of a poor person by his brother and his neighbor, rich merchants who visited other kingdoms, the importance of a man himself following the rules he sets for other people's behavior, the spite of a man for a woman who rejected him, the relative lack of enthusiasm of a wife for sex as compared to her husband, a mother giving up her own comfort for that of her child, the revenge killing of a murderer by the dead man's friends, the joy of seeing a loved one after years of separation, that life is more sad than happy, that lost money can be retrieved, but time lost is lost forever.

Other stories in the Canterbury Tales were about two men who did not remain friends after they fell in love with the same woman, about a child who preferred to learn from an older child than from his schoolteacher, about a wife who convinced her husband not to avenge her beating for the sake of peace, about a man who woke up from bad dreams full of fear, about a man wanting to marry a beautiful woman but later realizing a plain wife would not be pursued by other men, about a man who drank so much wine that he lost his mental and physical powers, about a woman who married for money instead of love, about a man who said something in frustration which he didn't mean, about a person brought up in poverty who endured adversity better than one brought up in wealth, about a wife who was loving and wise, about a good marriage being more valuable than money, about a virgin who committed suicide rather than be raped, about a wife persuaded to adultery by a man who said he would otherwise kill himself, about three men who found a pile of gold and murdered each other to take it all, about an angry man who wanted to kill, about a malicious man who had joy in seeing other men in trouble and misfortune, about a man whose face turned red in shame, about a wife expecting to have half of what her husband owned.

Political songs and poems were written about the evil times of King Edward II, the military triumphs of King Edward III, and the complaints of the poor against their oppressors, such as "Song of the Husbandman". John Gower wrote moralizing poems on the villein's revolt, the sins of the clergy and attorneys, and the bad rule of King Richard II, who in 1377 succeeded Edward III. Robin Hood ballads were popular. The minstrel, who was a honorable person, replaced the troubadour of older times.

There were many colleges at Oxford and Cambridge due to the prohibition of gifts to the church. Laymen instead of ecclesiastics were appointed as Chancellor. The Masters at Oxford got rid of ecclesiastical supervision by a bishop and archdeacon by 1368. One could be admitted as a student at age thirteen. The rate of maintenance for a student was 10d. weekly.

A Bachelor of Arts degree was granted after four years of study and an oral exam. Required reading in 1340 for the Bachelor's Degree was the new logic of Aristotle ("Prior and Posterior Analytics" e.g. on syllogistic logic and deduction, the "Topics", or the "Sophistical Refutations", e.g. logical fallacies such as from 'All A are B' to 'All B are A'), and a selection from these Aristotle works on physics: "Of Heaven and Earth", "On the Soul", "Of meteors", "Of Birth and Decay", or "Of Feeling and What is Felt" with "Of Memory and Recollection" and "Of Sleep and Waking", or "Of the Movement of Animals" with "Of Minor Points in Natural History".

A Master of Arts degree could be awarded after three more years of study and teaching. A Doctorate degrees in theology required ten more years of study. A Doctorate in civil or canon law required eight more years. A man with a degree in canon law who wanted to practice in a certain bishop's court had to first satisfy this bishop of his competence.

Another source of legal learning was in London, where the guilds gave rise to the Inns of Court. They used the Register of Writs, the case law of the Year Books, and disputation to teach their students.

For a doctorate in medicine from Oxford or Cambridge, five more years plus two years of practice were required. Surgery was not taught because it was considered manual labor, and there was some feeling that it was a sacrilege and dishonorable. Urinalysis and pulse beat were used for diagnosis. Epilepsy and apoplexy were understood as spasms inside the head. It was known what substances served as laxatives and diuretics. Teeth were extracted, eye cataracts were removed with a silver needle, and skin from the arm was grafted onto a mutilated face.

Englishmen who had collected books on philosophy, medicine, astronomy, and history and literature books from the continent gave their collections to the universities, which started their libraries. Paper supplemented parchment, so there were more books.

England was still an agricultural rather than a manufacturing country. Imported were cloth, silks, linen, velvets, furs, glass, wines, candles, millstones, amber, iron, and mercury. Exported were wool, leather, lead, tin, and alabaster for sculpturing. Merchant adventurers came to manufacture cloth good enough for export and began to buy up raw wool in such quantity that its export declined. They took their cloth abroad to sell, personally or by agents.