Researchers have recently started acknowledging the various positive psychology approaches and inputs that safeguard the individuals against stress and mental problems. Positive mental health and Flourishing are the present day concepts which have contributed widely to the area of well being. The present investigation aimed to study the gender differences and the relationship of Flourishing with optimism, resilience and self-esteem among adolescents. A random sample comprising 50 males and 50 females (N=100) ranging from 15 to 17 years of age was selected from Patiala, India. Participants completed a questionnaire booklet consisting of a demographic form, The Flourishing Scale (Diener et al., 2009), The Brief Resilience Scale (Smith et al., 2008), The Life Orientation Test -Revised (Scheier et al., 1994) and The Rosenberg Self- Esteem Scale (Rosenberg, 1965). Results revealed that males scored significantly higher on Flourishing, Optimism and Self-esteem as compared to females. Scores were found to be non-significant on the correlate of Resilience. Gender differences were found to be significant for Flourishing, optimism and self-esteem only. Various positive psychology interventions can be utilized at school level to enhance flourishing and psychological well being among adolescents. More research needs to be done in order to better understand the relationship between chosen variables among adolescents.