This commentary on Sehrbrock’s “Social Thirdness: Intersubjective Conceptions of the Experience of Gender Prejudice” highlights the role of social thirdness and its breakdown across a variety of domains, clinically and cross-culturally. It expands upon the concept of White Fragility, introducing the concept of mythological fragility—one that pertains to the need to maintain a person’s and/or a culture’s collective psychological organization and their essential ties to important others. The role of “horsing around”—the exercise of an expansive sense of play, freedom, creativity, passion, and authenticity—is essential not only in early life, but in the clinical setting, allowed, or sometimes disallowed, in the context of clinical psychoanalysis. This commentary argues, in agreement with Sehrbrock, that clinical work should provide a space in which both patient and analyst can indeed “horse around” and then see what becomes of it. This includes the adoption of an attitude of constructive uncertainty and of striving to be open to surprise, however welcome or unwelcome that surprise may be.