Akaranga, Stephen I.Ongong’a, Jude J.2018-02-122018-02-122013International Journal of Education and Research Vol. 1 No. 8 August 20132201-63332201-6740http://ir-library.ku.ac.ke/handle/123456789/18198Research ArticleThe term conundrum may mean a tricky problem that is difficult to solve (Oxford Advanced Learners Dictionary, 2000: 251). It describes the problems of the African patriarchal society in which the sex-based assignment of roles projects a spectre of inferiority and unworthiness over women while casting the characteristics of superiority on to men (cf. Lumumba et al, 2011:99). Traditionally, most Africans tend to assume the position of women, and the Maasai of Kenya are not an exception. Among the Maasai like most Africans, gender inequality and inequity are fundamental structures of social hierarchy believed to shape how people are related within the society. Being based on social relations, gender conundrums are part and parcel of the Maasai daily life and seem to be more pronounced in sexual relations. The argument of this paper is: HIV/AIDS is transmitted through; sexual contact, and exposure to infected blood or blood components and prenatally from the mother to the neonate (Dennis et al, 1989:31). The paper attempts to answer the following questions: What are the patriarchal practices that lead to sexual oppression of women such as; female genital mutilation, widow remarriage, polygamy; what is the negative impact of marriage arrangements between young girls and elderly men among the Maasai? Is the practice of sharing women among age mates still practiced among the Maasai? And if so, isn’t it a common path of HIV infections? To actualize our investigation, the paper analyzes the cultural education system for socializing girls and suggests ways of ameliorating such patriarchal and cultural tendencies. This was done through field research involving administration of questionnaires to various groups apart from oral discussions with some elders from the Maasai community.enConundrumCulturePatriarchalMatrifocalHuman rightsHIV/ AIDSReligionGender equity and equalityArticle