Teenage motherhood is a situation in which a girl in teenage years, that is, 13-19 years is a mother or has a child. Globally, a third of teenage mothers live in India whereas the least affected country by teenage motherhood in the world is Japan. In Africa, it is estimated that approximately 5.5 million girls between 15-19 years are mothers .Of these 62% live in Sub Saharan Africa. In Kenya, 13,000 girls leave school every year due to teenage pregnancy. The relationship between teenage motherhood and schooling is explicit; when teenagers become pregnant and consequently mothers they abandon schooling altogether. Stigmatization and discrimination by teachers, parents, fellow students and the immediate society are the major causes for discontinuing school. In turn, the girls feel that they deserve to be punished for getting pregnant by dropping out of school or are too shy to return to school. By discontinuing school, teenage motherhood spells a blink future for both the teenager and her child. This situation can be reversed, given Kenya's return to school policy. The policy calls for counseling for the girl, the parents, teachers and other students in the school. Nevertheless, the lack of legal backing or any official communication on how to implement the policy in schools makes it weak. Hence there is need to de-stigmatize teenage motherhood in an attempt to win back the girls to school. This paper elaborate on the question of teenage motherhood (causes and effects) and delves into the issue of teenage motherhood stigmatization and the need for the society to de-stigmatize teenage motherhood to enable the girls achieve education. The paper contributes to the ongoing debate on teenage motherhood. It also sensitizes the policy makers, educationists and the public on the need to recast their perception towards teenage motherhood and specifically on the social stigma associated with this old age problem.