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The aim of the present study was to compare self-destructiveness, fear of failure, and the big five personality traits in adolescent boys in divorced and normal families, employing a causal-comparative method. Ninety boys (of divorced and normal families, 45 in each group) were selected through purposeful sampling method for teenagers from divorced families and random sampling for teenagers from normal families. All of which were 15 to18 year-old boys studying in the second grade of high school in Karaj. To collect the data, Chronic self-destructiveness Scale (CSDS), Performance Failure Appraisal Inventory (PFAI) and NEO Five Factor Inventory (NEO-FFI) were run, and Multivariate analysis of variance test was used for analysis of data. Results showed that chronic self-destructiveness (F=94/64, p ≤ .001), inconsideration and lack of commitment (F=28/818, p ≤ .001), neglect (F=160/60, p ≤ .001), risk taking (F=43/543, p ≤ .001), stupefaction (F=52/933, p ≤ .001), fear of failure (F=1238/00, p ≤ .001), fear of experiencing shame and embarrassment (F= 1035 / 45 , p ≤ .001), fear of devaluing one's self-esteem (F = 1600 / 64 , p ≤ .001), fear of having an uncertain future (F = 1507 / 61 , p ≤ .001 ) ), fear of losing interest from important others (F= 69 / 872 , p ≤ .001) and neuroticism (F = 94 / 2202 , p ≤ .001) were higher in adolescent boys with divorced families than normal ones. In other dimensions of the big five, extraversion (F= 1719 / 52, p ≤ .001), openness to experience (F = 47 / 12, p ≤ .001), agreeableness (F = 3032 / 96, p ≤ .001), and conscientiousness (F= 1788 / 59, p ≤ .001), the mean scores in adolescent boys with normal families were higher than the ones from divorced. The negative experiences, the absence of a caring parent, and the lack of a sense of security in divorced families can be the reasons behind the higher rate of self-destructiveness and fear of success in adolescents from divorced families.