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This study investigates the role of family relationships and psychoticism in relation to homophobic bullying in adolescence. Participants were 394 adolescents and young adults, (164 boys and 230 girls) aged from 15 to 20 years. Participants completed the Homophobic Bullying Scale, to investigate bullying towards gay males and lesbians, the Inventory of Parent and Peer Attachment, to measure maternal and paternal trust, communication and alienation, and the Symptom Check-List-90-R, to evaluate psychoticism. The results show that, in the first mediation model, psychoticism strongly mediated the impact of maternal trust and alienation on bullying towards gay males. Moreover, in the second mediation model, psychoticism strongly mediated the impact of paternal alienation on bullying towards gay males. Theoretical and practical implications are discussed.