ABSTRACT. Adolescence is a transition phase filled with doubt and instability. During these transitions, some obstacles are often perceived as more intense and frequently cause adolescents to feel sad. This study was aimed to identify how male and female adolescents perceived sadness. A total number of 461 students, 273 females and 188 males, all of whom were high school students in Yogyakarta, completed an open-ended questionnaire, developed by Kim and Park (2006). The data was categorized, open-coded, axial-coded, and later cross-tabulated. Results demonstrated that females perceive negative moments as a life-lesson (30.4%), self reflection (13.9%), disruption (13.6%), life’s obstacles (8.1%), motivation (6.6%), memorable moments (6.6%), and lastly as a spiritual-lesson (2.6%). While males view sadness as a life lesson (22.9%), disruption (15.4%), self-reflection (11.2%), motivation (9.6%), memorable moments (5.9%), life’s obstacles (5.3%), and lastly as a spiritual lesson (3.2%). This result was later divided into two types of perception, the positive approach, containing life lesson, self-reflection, motivation, and spiritual lesson, and the negative approach, which are sadness as disruption, memorable moments, and life’s obstacles. This study concludes that both Indonesian male and female adolescent mainly took a positive perception on sadness as a life lesson, with only 27% of them viewing it as negative.