The specificity of educational contexts as mediators of social development through positive interactions is critical to children’s involvement in the kindergarten and therefore for their holistic development. The qualities of teacher-child interactions enhance the child’s self-esteem and autonomy, promoting peer acceptance and providing a successful learning experience. The purpose of this study was to investigate whether the characteristic of gender and age are related to the acquisition of social skills of children attending kindergarten in a portuguese-speaking environment. The sample is composed of 581 children, age from 2 to 7 years old, who attended preschool education on average 18 months ago. Social Skills subscale (EAS) and Behavior Problems (EPC) was applied to the “Behavioral Scale for Preschool-PKBSpt” (Gomes & Pereira, 2012), Portuguese version of PKBS-2 (Merrell, 2002), Likert-type, four response levels, which seeks to assess the social and emotional skills, and behavior problems in early childhood, with the participation of educators. The Statistical Package for Social Sciences (SPSS), version 17.0 for Windows. The main results show that there are gender differences in the level of social skills. The girls reveal behaviors based on Social Cooperation and Social Interaction. The boys show Attention Problems/Overactive and Antisocial Behavior/Aggressive. Older children have the highest average level Social Cooperation and Social Independence. In the dimensions of behavior problems, the youngest children (3 and 4 years) had higher mean values, either in the factor Attention Problem/Overactive or the Antisocial/Aggressive. Older children (6 years old) had statistically significant differences in the problems of the type Social Withdrawal and Anxiety-Somatic problems. The child’s gender and age variables are important factors and should be included in educational practices, taking into account the development of social skills of children attending in preschool. Promoting articulated and differentiated development can prevent maladaptive behaviors in young adults. Finally thoughts are given on the implications of this study in the level of children’s involvement within their educational contexts.