Recent evidence suggests that psychopathy is a trait continuum. This has unappreciated implications for understanding the selective advantage of psychopathic traits. Although clinical psychopathy is typically construed as a strategy of unconditional defection, subclinical psychopathy may promote strategic conditional defection, broadening the adaptive niche of psychopathy within human societies. To test this, we focus on a ubiquitous real-life source of conditional behaviour: the expected relational value of social partners, both in terms of their quality and the likely quantity of future interactions with them. We allow for conversational interaction among participants prior to their playing an unannounced, one-shot prisoner's dilemma game, which fosters naturalistic interpersonal evaluation and conditional behaviour, while controlling punishment and reputation effects. Individuals scoring higher on factor 1 (callous affect, interpersonal manipulation) of the Levenson self-report psychopathy scale defected conditionally on two kinds of lowvalue partners: those who interrupted them more during the conversation, and those with whom they failed to discover cues to future interaction. Both interaction effects support the hypothesis that subclinical primary psychopathy potentiates defection on those with low expected relational value. These data clarify the function and form of psychopathic traits, while highlighting adaptive variation in human social strategies.