Results from cumulative years of the National Demographic and Health Survey and the latest result of the 2011 Family Health Survey, shows that teenage pregnancy in the Philippines, measured as the proportion of women who have begun childbearing in their teen years, has been steadily rising over a 35-year period. These teenage mothers are predominantly poor, reside in rural areas and have low educational attainment. However, this paper observes a trend of increasing proportions of teenagers who are not poor, who have better education and are residents of urban areas, who have begun childbearing in their teens. Among the factors that could help explain this trend are the younger age at menarche, premarital sexual activity at a young age, the rise in cohabiting unions in this age group and the possible decrease in the stigma of out-of-wedlock pregnancy.