Willingness to argue is associated with higher level thinking. The authors tested the relation between ways of knowing—involving separate knowing (i.e., playing the devil's advocate) and connected knowing (i.e., empathic understanding)—and students' willingness to argue. Participants were 171 male and 231 female college undergraduates who completed assessments in ways of knowing and willingness to argue. Also, the participants defined the word argument in their own words. After the authors controlled for demographic variables, endorsement of separate knowing predicted willingness to argue. Students with high scores in separate knowing (objective, adversarial knowing) and connected knowing (subjective, empathic knowing) indicated more willingness to argue. Furthermore, these same students defined argument as a constructive form of communication. Students with low scores in separate knowing defined argument as an emotional battle with the goal of psychological harm. This negative perspective could be an impediment to engaging students in classroom debate and critical thinking.