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Philosopher-psychologist William James was a renowned educator during the Progressive era who taught with a pedagogy that married habit with creativity. In this paper, the author reconciles these two opposing theories to present a pedagogy of “relational habits.” Examining the theory of habit as propounded by James in concert with his creative and spontaneous teaching pedagogy, opportunities are presented to educators to consider how “relational habits” in pedagogy could be implemented in education today. The question is: “How can teachers build positive and productive teacher-student relationships balancing habit and creativity?” Using “relational habits,” teachers continually and habitually reflect on their practice by attending and being responsive to the needs and interests of their students through creativity and spontaneity.