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Introduction There is evidence of an association between the practice of intentional unsafe sex among men who have sex with men ( MSM) and sensation seeking and impulsivity. However, other aspects of personality have been less frequently investigated. Aims This study aims to investigate the association between the practice of intentional unsafe sex and personality traits in individuals who sought treatment and met the criteria for compulsive sexual behavior in São Paulo, Brazil. Methods The sample consisted of 69 sexually compulsive MSM. The participants underwent psychiatric evaluation and an interview to define intentional condomless sex and completed self-report instruments. Main Outcome Measures The participants completed the following measures: the Temperament and Character Inventory and the Sexual Compulsivity Scale. Results Twenty-five participants (36%) reported intentional unsafe sex with casual partners, of whom 84% were gay and 16% bisexual ( P < 0.05). Fifteen (22%) individuals reported being HIV positive, and 11 (73%) of them practiced intentional unprotected anal intercourse ( P < 0.05). The mean of sexual compulsivity was associated with men who engaged in intentional unsafe sex ( P = 0.01). Men who reported intentional unsafe sex scored significantly higher on the novelty seeking temperament dimension ( P < 0.05) and scored significantly lower on the self-directedness character dimension ( P < 0.001). However, self-directedness predicted intentional unsafe sex in the multiple logistic regression ( P = 0.001). Conclusions Sexually compulsive individuals who practiced intentional unsafe sex presented lower self-directedness than the group who did not engage in intentional unsafe sex, which suggests less autonomy regarding life itself. To the best of our knowledge, this is the first study to consider intentional unsafe sex in sexually compulsive men. Amaral MLS, Abdo CHN, Tavares H, and Scanavino MdeT. Personality among sexually compulsive men who practice intentional unsafe sex in São Paulo, Brazil. J Sex Med 2015;12:557-566. [ABSTRACT FROM AUTHOR]