For the psychoanalytic mind, the ubiquitous phrase “I don't know” resonates with unconscious power. The phrase implies that, in fact, there is something to be known. This paper looks at the recurring appearance of “I don't know” in excerpts from one and a half years of sessions with a middle aged man, “G,” observed during a psychoanalytic externship through the New York Graduate School of Psychoanalysis. Using the concepts of “symbolization,” the making of meaning through symbols, and “desymbolization,” the destruction of meaning through defenses such as denial, disavowal, and going blank, the evolution in meaning and function of “I don't know” for G is studied. This paper suggests that through the influence of a symbolizing, analytic perspective, the initial desymbolized state of G transforms to a more reflective, symbolized state.