This article describes an assignment in a History of Psychology course used to enhance student retention of material and increase student interest and discussion of the long-standing debate between humanistic and mechanistic models in psychology. Adapted from William James's (1955) automatic sweetheart question, the assignment asks students to imagine if they could love their sweetheart after finding out that he or she was not a conscious human being but a technologically advanced machine. Compared to a control group, students completing the assignment demonstrated improved performance on a posttest quiz. Students also reported the assignment was interesting, had educational value, and helped them understand the historical significance of a fundamental debate in the History of Psychology.