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Description: Before dialecticism became a topic of empirical inquiry in cultural psychology, scholars in related disciplines has discussed dialecticism as a model of human development, as an essential component of maturity and wisdom. This review chapter bridged these two perspectives, comparing conceptualizations of dialecticism in developmental and cultural psychology. After reviewing historical portrayals of dialecticism in various philosophical traditions, this chapter provides comparison of historical characterizations with the contemporary treatment of dialecticism in human development and cultural psychology. Both streams -- developmental and cross-cultural -- are proposed as essential for an integral understanding of the construct. Subsequently, the chapter discusses the emerging developmental models of dialecticism across the lifespan and reviews the accompanying empirical evidence, situating it in a cross-cultural context. It concludes with an outline of future directions of research on dialectical thought, with attention to psychological and socio-cultural processes engendering dialecticism across the lifespan.