Guilt and shame are important human emotions, which have been studied by several different disciplines. Seminal and recent inputs in Psychology (particularly Psychoanalysis) and Psychiatry are briefly reviewed including cross-cultural considerations and developmental psychology studies on these emotions. Yet this keynote focuses in the phenomenology and epistemology of guilt and shame as complex emotions. This includes considering that guilt is experienced in two moments (decompressed into a moment of negligence and another of guilt) while shame only in one moment (prolonged in a “frozen now”). All the inputs have suggested an operationalization of epistemic and phenomenic differences considering their context, formal object, particular object and action tendency. Lastly it refers to the relation of these experiences with psychopathology and nosology concerning their adaptive and maladaptive nature, their relation with empathy as well as their presence in several disorders such as anxious, depressive and obsessive compulsive sorts.