Against the backdrop of Rahel JeaggJeaggi, R.i’s critique of Harry FrankfurtFrankfurt, H.’s theory of personhood the chapter analyzes the normative import of second-order emotions. The idea is that a disapproving second-order emotional response to a first-order emotional responses that takes us aback, constitutes a moment of normative ambivalence prompted by the unanticipated turn of events that initially gave rise to the first-order response. In view of the crucial role played by normative ambivalation in rational normative self-criticism, to what extent can such moments be sought proactively?