It is a commonplace that the teaching of English language and literature in India commenced as an Imperial enterprise, to create assistants in the colonial enterprise. The aim was to create “a class of persons, Indian in blood and colour, but English in taste, in opinions, in morals, and in intellect”. Yet the teaching of English literature continued in the post-Independence period. As more and more colleges and universities, both private and public, were opened through the decades making Higher Education accessible to the poor and lower classes, English both as a medium of instruction and as content of instruction propagated itself. This is not simply because it is a part of India’s cultural legacy from a turbulent period of history. Daily interaction with students who are involved with it, students --- and this cannot be emphasised enough ---, disadvantaged students whose families reflect the vast majority of Indians brings forth a chaotic mosaic of many languages, religions, conflicting cultures and disparate economic classes which is reflected in the composition of the student body of an average college, specially the government funded colleges. Additionally many of the students are what is categorised as “first generation learners”, that is, students whose parents are illiterate or semi-illiterate. The problem for any sincere committed lecturer at the tertiary level is how to navigate such treacherous shoals while imparting a liberal education and trying to make students appreciate an alien literature in an alien tongue. For example, how should a faculty member explain the connotation of idol worshipper in a class comprising of Hindu, Muslim and Christian students without exacerbating religious tension? A micro study of a single college – Surendranath College for Women in Kolkata in this case – will serve as a guide in this article about the hazards and stratagems of teaching English literature in a post-colonised India.