Contemplative pedagogy is part of the larger emerging field of Contemplative Studies. Louis Komjathy (2018) has observed three characteristics shared by various aspects of Contemplative Studies: practice commitment, critical subjectivity, and character development. This paper uses these three characteristics to describe and define a “contemplative course” and “contemplative writing.” First, this paper describes a contemplative approach to the development of the General Education course “Curiosity, Playfulness, Creativity” in terms of the author’s practice commitment, critical subjectivity, and character development. Second, the paper discusses these three characteristics as they apply to students’ contemplative writing experiences and assignments in that course. These notes on theory and practice may provide inspiration for educators across disciplines to craft context-informed contemplative courses and experiences that tap into the radical, transformative power of contemplative traditions.