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Among Hale's classmates was (afterward Major) Benjamin Tallmadge, who had charge of André soon after his arrest. With William Robinson and Ezra Samson he was engaged with Hale at their graduation, in a Latin syllogistic dispute, followed by a debate on the question, "Whether the education of daughters be not, without any just reason, more neglected than that of the sons?"

"In this debate Hale was triumphant," wrote James Hillhouse, another of his classmates, who was a few months his junior. "He was the champion of 'The Daughters,' and most ably advocated their cause. You may be sure that he received the plaudits of the ladies present."

On leaving college, Hale engaged in school-teaching for nearly two years. He first taught a select school at East Haddam, on the left bank of the Connecticut River, then a place of much wealth.

In 1774 he was called to the position of preceptor in the Union Grammar-School at New London, an institution of high grade, intended to furnish facilities for a thorough English education and the classical preparation necessary for entering college. The school-building stood on State Street. Young Hale was appointed its first preceptor after its organization. It was a high compliment to his ability.