The family constitutes the basic ecology where adolescents' assertiveness is manifested. However, there is a darker side to some parents' behaviours that belies these virtues. This study sought to explore affluent Parents' behaviour on adolescents' assertiveness. The research questions were: What are the levels of assertiveness among adolescents in affluent families? What behaviours are exhibited by affluent parents? How do these behaviours influence assertiveness among adolescents? How can affluent parents' best facilitate development towards adolescent assertiveness? Eric Erickson's theory of psychosocial development was used and a Convergent parallel design. Quantitative applied cross-sectional while qualitative was phenomenological. The target population was 24507 with a sample size of 600 respondents consisting of 100 parents and 80 house helps purposefully sampled; 400 adolescents and 20 local officers randomly sampled. The study used Questionnaires for collecting data fromboth parents and adolescents, interview guide for local officers and house helps and a focus group discussion was done with 20 parents for in-depth data.