Previous research suggests that avoiding the expression of emotion may be associated with impaired mental health, although empirical evidence is inconsistent. In this investigation, ambivalence over the expression of emotion is understood as an approach-avoidance conflict between a desire to express emotion and a fear of experiencing negative consequences. Consistent with a diathesis-stress model of depression, we assumed that in stressful situations strong ambivalence over the expression of emotion constitutes an intrapersonal vulnerability for the development of depressiveness. In a cross-sectional survey with an at-risk sample of 112 unemployed subjects, ambivalence over the expression of emotion statistically moderated the prediction of depressiveness by insufficient need satisfaction/stress. The present study provides initial support for the notion that strong ambivalence over the expression of emotion may impede subjects’ potential to cope with extreme stressors such as unemployment and may foster associated depressive states. Psychological interventions in this population may identify and target individual sources of ambivalence contingent on unemployment.