This paper presents the findings of a study on the experiences of secondary school teachers on teaching pregnant learners in Limpopo Province. A qualitative, exploratory, descriptive and contextual design was used. Semi-structured interviews were conducted with ten purposively selected secondary school teachers. Data analysis yielded six themes, which are: (1) identification of pregnant learners; (2) continuation of pregnant learners' school career; (3) dilemmas related to school-attending pregnant learners; (4) support of school-attending pregnant learners; (5) gender in pregnancy caretaking; and (6) communication and cooperation between teachers and parents. Teachers experienced challenges in identifying pregnant learners, and to meet their health needs as they lacked health related skills. Parents were not always cooperative towards teachers. It can be concluded that teachers face many dilemmas related to pregnant learners, and this requires a health facilitation model to enable teachers to assist pregnant learners such that they might better benefit from their schooling, and experience a positive health outcome.