The present study was designed to investigate the differences of psychological wellbeing and level of self - confidence among adolescence. The total random sample consisted of 120 adolescence (60 Male and 60 Female) who study in higher secondary schools in humanities stream from Nadia and Murshidabad district (West Bengal). The sample was equally divided in regard to gender also. Psychological wellbeing scale developed by D.S.Sisodia and Pooja Chaudhary and Self confidence was measured with the help of Agnihotri’s Self- Confidence Inventory developed by Dr. Rekha Gupta(1987) were used to collect the required data. Mean scores were computed and ‘t’ – test was applied to find out the differences between the group. The result of the study shows that gender had no significant impact on the Psychological wellbeing and Self-confidence of adolescence. The ‘r’ between psychological wellbeing and self –Confidence was 0.84.