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1943–1954: Education: Port of Spain and Oxford

Naipaul was enrolled in the government-run Queen's Royal College (QRC), an urban, cosmopolitan, high-performing school, which was designed and functioned in the fashion of a British boys' public school. Before he turned 17, he won a Trinidad Government scholarship to study abroad. He reflected later that the scholarship would have allowed him to study any subject at any institution of higher learning in the British Commonwealth, but that he chose to go to Oxford to do a degree in English. He went, he wrote, "in order at last to write...." In August 1950, Naipaul boarded a Pan Am flight to New York, continuing the next day by boat to London. He left Trinidad, like the narrator of Miguel Street, hardening himself to the emotion displayed by his family. For recording the impressions of his journey, Naipaul purchased a pad of paper and a copying pencil, noting, "I had bought the pad and pencil because I was travelling to become a writer, and I had to start." The copious notes and letters from that time were to become the basis for the chapter "Journey" in Naipaul's novel The Enigma of Arrival written 37 years later.

Arriving at Oxford for the Michaelmas term, 1950, Naipaul judged himself adequately prepared for his studies; in the judgment of his Latin tutor, Peter Bayley, Naipaul showed promise and poise. But, a year later, in Naipaul's estimation, his attempts at writing felt contrived. Unsure of his ability and calling, and lonely, he became depressed. By late March 1952, plans were made for his return to Trinidad in the summer. His father put down a quarter of the passage. However, in early April, in the vacs before the Trinity term, Naipaul took an impulsive trip to Spain, and quickly spent all he had saved. Attempting an explanation to his family, he called it "a nervous breakdown". Thirty years later, he was to call it "something like a mental illness."

Earlier in 1952, at a college play, Naipaul had met Patricia Ann Hale, a history student. Hale and Naipaul formed a close friendship, which eventually developed into a sexual relationship. With Hale's support, Naipaul began to recover and gradually to write. In turn, she became a partner in planning his career. When they told their families about their relationship, the response was unenthusiastic; from her family it was hostile. In June 1953, both Naipaul and Hale graduated, both receiving, in his words, "a damn, bloody,... second." J. R. R. Tolkien, professor of Anglo-Saxon at Oxford, however, judged Naipaul's Anglo-Saxon paper to have been the best in the university.

In Trinidad, Naipaul's father had had a coronary thrombosis in early 1953, and lost his job at the Guardian in the summer. In October 1953, Seepersad Naipaul died. By Hindu tenets, it fell to Naipaul to light the funeral pyre—it was the mandatory ritual of the eldest son. But since there was not the time nor the money for Naipaul to return, his eight-year-old brother, Shiva Naipaul, performed the final rites of cremation. "The event marked him," Naipaul wrote about his brother. "That death and cremation were his private wound."

Through the summer and autumn of 1953, Naipaul was financially depleted. His prospects for employment in frugal post-war Britain were unpromising, his applications to jobs overseas repeatedly rejected, and his attempts at writing as yet haphazard. Working off and on at odd jobs, borrowing money from Pat or his family in Trinidad, Naipaul reluctantly enrolled for a B. Litt. post-graduate degree at Oxford in English Literature. In December 1953, he failed his first B.Litt. exam. Although he passed the second written examination, his viva voce, in February 1954, with F. P. Wilson, an Elizabethan scholar and Merton Professor of English Literature at Oxford, did not go well. He was failed overall for the B.Litt. degree. With that also ended all hopes of being supported for academic studies at Oxford. Naipaul would later say that he 'hated Oxford'.