Males are still underrepresented in the office management environment and this article pertains to the tendency to discriminate against men students studying towards administrative and office-related qualifications. The purpose of the study was to determine whether the perceptions (regarding various barriers in executing their studies) of male office management students in a female-dominated occupational career choice have changed since 2002 and to determine the level and quality of guidance received on entering this field. The study encompassed a literature review and empirical surveys (2002 and 2010) which were conducted by means of structured questionnaires. Although there was an overall increase in male office management student numbers, gender discrimination undoubtedly, as well as ineffective or no career guidance still had a negative effect on these individuals and their career choices. Educators and career guidance officers should take every possible measure to reduce all gender segregation and become more sensitive to and actually provide career guidance to students planning to make career choices.