Aim: This paper aims to determine the difference between the health and social conditions of women who had their first pregnancy as teenagers (13-19 years old) and those who had their first pregnancy during post-adolescence (20-41 years old). Materials and Methods: The results were based on a structured, 60-item interview schedule with 132 cases (71 teenagers and 61 women ≥ 20 year old) in Trinidad and Tobago. These cases comprised Afro-Trinidadians, Indo-Trinidadians, and Trinidadians of “Mixed” ancestry, who were all recruited by nurses in three health centers in Northern Trinidad, during the period October 2004 to October 2005. The main issues of concern regarding the respondents were history of stillbirths, abortion, contraceptive use, intended family size, marital status, and employment status. Data were analyzed, using Statistical Package for the Social Sciences (SPSS) 12.0. Results: While the study shows similarity between the two groups of respondents, in terms of their breast-feeding practices, there were differences regarding teenage mothers who experienced a higher level of unemployment (35%), single and common law relationships (81%), and lower contraceptive use (11.8%). The older mothers were more likely to be classified as unskilled (34.4%) compared to 22.5% for the teen group. Conclusions: The findings reveal that teenage pregnancy is considered a risk factor and has socio-economic implications regarding the lives of the mother and child in terms health, income, employment, and marital status.