In this chapter, we explore the relationship between counterfactuals and meaning. To do so, we have organized our thoughts into three sections. First, we review previous research on the role of counterfactual mind-sets, or cognitive orientations, in establishing causal relationships. Second, we explore the implications of the deliberate construction of counterfactuals for the emergence of personal meaning. We claim that the psychosocial construction of autobiographical life stories are inexorably linked with counterfactual thought. Third, we identify unanswered questions regarding the relationship between counterfactual thought and meaning.