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The Friendlys wintered in Florida, causing him to miss periods of school. Nonetheless, Henry skipped multiple grades and took an interest in American history and English literature, though avoided science; his particular interests were in English writers George Eliot and William Makepeace Thackeray. He attended the Elmira Free Academy, excelling academically as an involved student, and came to praise the system there. He fondly remembered the school as a place with "very devoted and dedicated teachers who worked for a pittance." Friendly was the editor-in-chief of the academy's newspaper, The Vindex, in addition to having engagements on the student council, debate team, and its "Class Song and Motto Committee."

Friendly (topmost right) pictured in 1917 with other members of the Elmira Free Academy Debate Society

At the onset of World War I, Friendly eagerly supported the German cause, but switched sides when the United States entered the war. He abandoned his initial support for Germany and began soliciting war bonds in nearby towns while still enrolled at Elmira. In 1919, he graduated from the academy as valedictorian, attaining the highest scores ever recorded in the New York Regents Examinations. It was at Elmira that Friendly developed core personal values, learning to value culture and responsibility. However, his reclusivity, combined with a lack of close relationships, contributed to emotional issues that would persist over the course of his life. During this period, he experienced his first serious exposure to law as a young teenager while serving as an expert witness in a trial brought by his father for a breach of warranty. By means of a friend's father, a lawyer, he learned to respect law and societal boundaries.

Cornell University in Ithaca, New York, had been the most convenient choice for college, though Friendly opted instead to matriculate at Harvard College, drawn by the school's expansive catalogue. Emergent challenges with his vision nearly delayed his college entry by a year. He enrolled in the fall of 1919 at age sixteen and passed a competitive examination which allowed him to skip a basic English course. The university's only student from Elmira, he came to be alienated from other freshman students, who were two years his senior and less involved intellectually. The campus social scene at the time was strictly segregated among wealthy Christian families, who often coalesced in isolated clubs.

Friendly was a taciturn undergraduate who lacked social skills. John Mason Brown unsuccessfully offered him a position on The Harvard Advocate literary magazine, which he rejected owing to a dislike of creative writing. He joined the university's debate team, though resigned for better commitments. Despite an absence of fellowship, Friendly continued to excel in his studies with a focus in history, philosophy, and government, achieving superlative grades every year. He cherished the intellectual challenges of understanding history, a pursuit reinforced by Harvard's modern approach that emphasized the field's intellectual and political aspects. Friendly's successes in the classroom were noticed by his peers. Future attorney Albert Gordon, a classmate at Harvard, later reflected upon his reputation: "we thought of him not only as the smartest in the class but the smartest at Harvard College."

In 1923, Friendly graduated with an A.B., summa cum laude, and was elected to the Phi Beta Kappa honor society. During his junior year, he had received the prestigious Bowdoin Prize for a paper entitled "The Fall of Naples: An Episode in the Risorgimento" which examined Italian statesmen Camillo Benso and Giuseppe Garibaldi. Friendly developed a passion for European history through courses with Charles Homer Haskins, Archibald Cary Coolidge, and Frederick Jackson Turner. He was also exposed to European diplomatic history under William Langer. In his senior year, Friendly took inspiration from Charles Howard McIlwain, whose course in medieval England he credited with being "by all odds the greatest educational experience I had at Harvard College." The historian broadened his knowledge of Latin and stressed the need to interpret documents as they were originally understood, a lesson adopted by Friendly when he ascended to the bench years later.