The present study examined when people decide to choose an expression that is based on critical thinking, and how situational and individual variables affect such a decision process. Given a conversation scenario including overgeneralization with two friends, participants decided whether to follow the conversation by a critical-thinking expression or not. The authors controlled purpose and topic as situational variables, and measured critical-thinking ability, critical-thinking disposition, and self-monitoring as individual variables. We conducted an experiment in which the situational variables were counterbalanced in a within-subject design with 60 university students. The results of logistic regression analysis showed differences within individuals in the decision process whether to choose a critical-thinking expression, and that some situational factors and some subscales of the individual measurements were related to the differences.