Entrapped in the parental aspiration of acquiring elite like proficiency in English pupils from the underprivileged sections appear to be precariously positioned in coping with the complexities involved in classroom pedagogical processes where, undue emphasis is given on the learning of English. Many of them happen to be first generation learners, and owing to which they find themselves overburdened by parental expectations. The pressure to perform is more intense from their parents’ side than from their teachers’ side. These parents themselves never went to schools but they seem to be well informed about the significance of good education and the benefits accruing from such education. The students, on the other hand, find a disjunction between the language of instruction and their MT (which also happens to be the community language). With English as the medium of instruction, most students struggle with an inherent incomprehensibility in the learning process. Consequently, the whole learning process appears to them as tardy, burdensome and ‘joyless’. By contrast, students from well off families have good exposure to the English language even outside school. Furthermore, they have access to internet, journals, magazines, newspapers, storybooks, movies and English speaking peer group and relatives. Their social capital enhances their linguist capital-they are more likely to become proficient in the English language than their underprivileged counterparts. The paper tries to bring forth challenges faced by these students from working class background by conducting ethnographic interviews.