Life history theory suggests that in risky and uncertain environments the optimal reproductive strategy is to reproduce early in order to maximize the probability of leaving any descendants at all. The fact that early menarche facilitates early reproduction provides an adaptationist rationale for our first two hypotheses: that women who experience more risky and uncertain environments early in life would have (1) earlier menarche and (2) earlier first births than women who experience less stress at an early age. Attachment theory and research provide the rationale for our second two hypotheses: that the subjective early experience of risky and uncertain environments (insecurity) is (3) part of an evolved mechanism for entraining alternative reproductive strategies contingent on environmental risk and uncertainty and (4) reflected in expected lifespan. Evidence from our pilot study of 100 women attending antenatal clinics at a large metropolitan hospital is consistent with all four hypotheses: Women reporting more troubled family relations early in life had earlier menarche, earlier first birth, were more likely to identify with insecure adult attachment styles, and expected shorter lifespans. Multivariate analyses show that early stress directly affected age at menarche and first birth, affected adult attachment in interaction with expected lifespan, but had no effect on expected lifespan, where its original effect was taken over by interactions between age at menarche and adult attachment as well as age at first birth and adult attachment. We discuss our results in terms of the need to combine evolutionary and developmental perspectives and the relation between early stress in general and father absence in particular.