Instead, he allied himself with the "Aristocrats" or "Puffmaniacs", a group of students who gathered in order to smoke and talk. As a town student and the son of a minister, however, he was able to move between social groups. He also became friends with Charles Chauncy Emerson (brother of Ralph Waldo Emerson), who was a year older. During sophomore year, Holmes was one of 20 students awarded the scholastic honor Deturs, which came with a copy of The Poems of James Graham, John Logan, and William Falconer. Despite his scholastic achievements, the young scholar admitted to a schoolmate from Andover that he did not "study as hard as I ought to'. He did, however, excel in languages and took classes in French, Italian and Spanish.
Holmes's academic interests and hobbies were divided among law, medicine, and writing. He was elected to Harvard's Hasty Pudding Club, for which he wrote humorous poems and songs, and the Phi Beta Kappa honor society. With two friends, he collaborated on a small book entitled Poetical Illustrations of the Athenaeum Gallery of Painting, which was a collection of satirical poems about the new art gallery in Boston. He was asked to provide an original work for his graduating class's commencement and wrote a "light and sarcastic" poem that met with great acclaim. Following graduation, Holmes intended to go into the legal profession, so he lived at home and studied at the Dane Law School. By January 1830, however, he was disenchanted with legal studies. "I am sick at heart of this place and almost everything connected to it", he wrote. "I know not what the temple of law may be to those who have entered it, but to me it seems very cold and cheerless about the threshold."