In view of the unprecedented escalation in unplanned teenage pregnancies in South Africa, this research study sought to explore contributing factors, consequences, challenges, needs and coping strategies surrounding teenage pregnancy. The study was based on a qualitative research paradigm. The research used purposive sampling as a strategy to target three particular categories of individuals for investigations (i.e. parents/caregivers, teenagers and teachers). Semi-structured interview schedules were the instruments used to gather data during face-to-face interviews with the participants. The sample consisted of eight teenage mothers and one expectant teenage mother in Grade 9 to Grade 12; six parents who had children who had experienced teenage pregnancy and six teachers who were or are teaching teenagers. In order to analyze the qualitative data, a typical form of thematic content analysis was utilised. The main conclusion based on the research findings was that the challenges, needs and coping strategies perceived by the three groups of participants were similar and associated with one another. Although most of the most of the findings coming to the fore have also been apparent in previous research studies, it enhanced the knowledge and understanding of the phenomenon of teenage pregnancy from a triangulation perspective, namely teenagers and primary role players in their lives. It is hoped that the recommendations made, based on the research findings, will lead to improved social work intervention strategies, and services offered by other people responsible for addressing this social problem in the South African context..