The study examined qualitatively the gendered perception of schooling amongst secondary school students. The research agenda emerged through the revealed evidence of what appeared to be an one-sided research approach to the study of gender issues through the quantitative methodologies. The study was therefore designed to determine the qualitative differences in the manner with which the students expressed their understanding of the roles of schooling upon their lives. To do this an observational single case study was designed and carried out in one of the secondary schools in Enugu State. The study, involved fifty-(50) participants, selected through the purposive sampling procedure. Data were collected through the participant observation, interviews, focus group discussions and the diary. Data collected were analyzed through the analytic induction and the grounded theorizing approaches. Both approaches emphasize the generation of theories through data from empirical studies. The results of the analyses show that not only are there qualitative differences in the way that boys and girls in the study responded to issues about schooling, results equally show that differences exist in the patterns of interaction and socialization processes amongst the boys and girls in the study. It is therefore the argument of this article that qualitative research such as the one represented in this article could play important supplementary role to quantitative research finding on gender issues in education. It is equally clear from this study that the qualitative methods of data collection and analyses have the ability to capture the internal processes within the individuals‟ lived experiences. This same ability at capturing internal processes, this article has argued, may not be achieved through the quantitative approaches especially when issues such as the contextual, cultural and historical dynamics of gender are concerned.