Volunteers (N = 322) in an online survey revealed the complex correlational patterns between the Dark Triad traits and two forms of “emotional deficiencies” (i.e., limited empathy and alexithymia) overall and in each sex. Each Dark Triad trait was associated with a unique pattern of emotional deficits. Psychopathy was correlated with limited overall empathy, difficulty describing feelings, and externally oriented thinking. Narcissism was associated with limited affective empathy and difficulty identifying feelings, whereas Machiavellianism was associated with externally oriented thinking. The Dark Triad mediated sex differences in empathy and externally oriented thinking. Structural Equation Modeling suggests that the differential facets of alexithymia predict different forms of limited empathy that in turn predict specific Dark Triad traits. Results are discussed using an evolutionary paradigm.