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Machiavellianism is a well-studied topic in several branches of psychology. Still, it has received little attention from a developmental perspective. Previous retrospective studies linked Machiavellianism to poor parental care, but actual reports of adolescents who live in their family of origin have been ignored so far. Therefore, we investigated the relationship between Machiavellianism and parental attachment in adolescence and possible sex differences based on life history theory. An adolescent sample ( N = 376; 17.27 ± .77 years of age) completed the Mach-IV and the maternal and paternal versions of revised Inventory of Parent and Peer Attachment (IPPA-R). According to our results, significant sex differences emerged in the relationship between Machiavellianism and attachment to parents. For girls, maternal alienation proved to be the only significant predictor of Machiavellianism, whereas for boys, low intensity and quality of verbal communication with father predicted higher levels of Machiavellianism. Results are discussed from an evolutionary perspective of socialization and from the perspective of emotion regulation.