We examine how individual metacognitive differences and the two selves – the​ experiencing and remembering selves – are related to individual risk attitudes. To track how the experiencing self makes judgments, participants in an experiment are primed over six weeks with macroeconomic and political news in an ecologically relevant period of a presidential election. Every Friday, the participants indicate their willingness to take risks at the moment. In Week 7, all participants are asked to rate the total experience of the six weeks. Rather than reporting hedonimeter totals, they show duration neglect and only the final moment matters for the retrospective judgment. Moreover, individual risk tolerance is higher when assessed by the remembering self than when judged by the experiencing self. Also, higher metacognitive ability is associated with higher levels of risk tolerance. However, participants of higher metacognitive ability still cannot avoid the System 1 bias of duration neglect. This is the first empirical work explicitly relating the two selves and Systems 1 and 2 thinking processes.