The Philomathean Society, one of the two chief literary societies on campus in the nineteenth century, was founded in 1831 by the remaining members of the older Henodelphisterian Society following the departure of nine of its members to found the Athenian Society in the previous year. Among these first Philomatheans were Lewis Bollman, James D. Maxwell, P. L. D. Mitchell, and the Dunns: James W., Samuel C., and W. McKee. The Athenian and Philomathean societies, whose creation resulted from factionalism within the Henodelphisterian Society (in part reflecting factionalism within the faculty), continued as rivals, albeit sometimes friendly ones, for some fifty years or so, dominating the extra-curricular life of Indiana College/University.

Literary societies gave students practice in speaking and writing through regular orations, essays, and debates, as well as filling a social role. Each society provided a valedictory speaker at Commencement; this most coveted position was reserved for a junior, who would bid goodbye to the graduating seniors. The next highest honor for an orator was to be chosen to represent his society at the joint Washington's birthday celebration, followed by those orators, essayists, and debaters who would compete in the annual contest between the two societies. Underclassmen were usually chosen to speak at an annual public exhibition of the society, at which the entire society would march into the hall two by two, wearing white ribbons (in the case of the Philomathean Society; the Athenians wore blue), with the president of the University at the head of the procession. The Philomathean Society's motto was "Doctrina vim promovet insitam," or "Doctrine promotes natural vigor."

The literary societies each had a hall and library of their own in the first college building on Seminary Square, which was destroyed by fire in 1854, and in the replacement building built in 1855. They were chartered directly by the General Assembly, but had some struggles with the faculty and Board of Trustees, who attempted to exert a high degree of control. Sometime around early 1863, the Trustees declared that the societies must have their speeches and invited speakers approved by the faculty ahead of time. The Philomathean society refused, saying they would stop holding public exhibitions rather than give in. The matter eventually blew over following a Philomathean commencement speech by the minister William Daily. Thomas D. Clark, in his history Indiana University: Midwestern Pioneer, calls this incident "Indiana University's first really important test of the principle of academic freedom" (172).

James Albert Woodburn, who was an Athenian like his father while at Indiana University, reports that in his father's time (1838-42) the literary societies had some forty to fifty members, and performed many of the functions that were later fulfilled by fraternities, which began to be established about 1845. In Woodburn's college days (in the 1870s) the chief fraternities would attempt to dominate the literary societies and win positions of honor within them for their members. Woodburn reports that the fraternities later lost interest in the literary societies when independent students were able to re-assert control of them.

However, one editorial writer for the Indiana Student perceived a decline in the literary societies as early as 1871. Professor David Starr Jordan, a few years before becoming president of Indiana University in 1885, contributed to this decline by giving an address which ridiculed the artificial style and lack of original substantive ideas of the old-fashioned college orators. As president, he led Indiana University in the direction of becoming specialized by academic areas, which led to the creation of more discipline-specific clubs and reinforced the dwindling of interest in the literary societies.

Also interest seems to have been diverted into the creation of alternative literary societies. The coed Independent Literary Society was founded in November 1885 by "Barbs" (non-fraternity men) frustrated with the control of the fraternities, and the Union Literary Society in the 1886-87 academic year. By March 1888 the latter had merged with the Athenian Society under the name Union-Athenian.

The Philomathean Society appears to have made a somewhat successful attempt to revive enthusiasm in literary societies in the late 1880s, and by December 1891 had 27 members. One-third of these 1891 members were women, although the society appears to have been exclusively for men for much of its earlier history; it is possible, though not certain, that this change was made when the constitution was revised in the fall of 1890. The resurgence was short lived and the Bloomington Telephone reported on 25 November 1892 that "On account of lack of interest (the) Philomathean society has died a natural death." Nevertheless, it was listed in the catalogue for the last time in 1893.