Although evolutionary psychology has been successful in explaining some species-typical and sex-differentiated adaptations, a large question that has largely eluded the field is this: How can the field successfully explain personality and individual differences? This article highlights some promising theoretical directions for tackling this question. These include life-history theory, costly signaling theory, environmental variability in fitness optima, frequency-dependent selection, mutation load, and flexibly contingent shifts in strategy according to environmental conditions. Tackling the explanatory question also requires progress on three fronts: (a) reframing some personality traits as forms of strategic individual differences; (b) providing a nonarbitrary, evolutionary-based formulation of environments as distributions and salience profiles of adaptive problems; and (c) identifying which strategies thrive and which falter in these differing problem-defined environments.