This study developed two specifications of the social skills deficit stress generation hypothesis: the "gender-incongruence" hypothesis to predict peer victimization and the "need for autonomy" hypothesis to predict conflict with authorities. These hypotheses were tested in a prospective large population cohort of 2,064 Dutch young adolescents. Social skills and pubertal timing were measured when the sample was about 11 years old, and stressful life events were measured 2.5 years later at follow-up. As predicted by the gender-incongruence hypothesis, poor assertion in boys and poor self-control in girls were associated with peer victimization. Consistent with the need for autonomy hypothesis, poor self-control was associated with conflict with authorities, in both boys and girls. Furthermore, early physical maturation exacerbated the effect of poor self-control on conflict with authorities for both genders. These specific associations provide more insights in the pathways that result in the experience of interpersonal stressors in young adolescents.