Japanese psychiatrists have proposed a new type of depression characterized by passing blame and irritability, which worsens on working days. This new type of depression is assumed to be closely associated with two personality traits: Interpersonal sensitivity, which reflects the tendency to be excessively concerned about or overreact to others’ negative evaluations, and privileged self, which reflects the tendency to pursue own pleasures at the expense of maintaining harmony with others. Although a previous longitudinal study showed that these traits can lead to interpersonal stress generation among university students, it did not control for the influence of baseline negative events, nor use a scale that separately assessed negative dependent events caused by the participants’ behaviors and negative independent events occurring outside the participants’ control. The current study addressed these limitations and investigated whether interpersonal sensitivity and privileged self led to stress generation and increased depressive symptoms. Undergraduate and graduate students in Japan (N = 265) responded to self-report measures twice at an interval of four weeks. The results indicated that privileged self was related to an increase in subsequent experiences of negative dependent and independent events after controlling for either category of events experienced at the baseline. These findings suggest that privileged self can lead to stress generation or the perception that surrounding circumstances are worse than they are. Furthermore, privileged self was associated with an increase in subsequent depressive symptoms via experiences of negative interpersonal dependent events.