Among the Dark Triad traits (psychopathy, narcissism, and Machiavellianism), Machiavellianism is uniquely associated with flexibility. This flexibility should result in the use of aggressive short‐term tactics only when they do not interfere with long‐term goals. Study 1 found that individuals high in Machiavellianism differed from those high in psychopathy with respect to retrospective accounts of negative mate retention tactics. Study 2 found an interaction between Machiavellianism and relationship type such that individuals high in Machiavellianism tempered the use of negative tactics for long‐term (but not short‐term) relationships. The findings highlight the flexibility of the Machiavellianism construct and its relevance to mating strategies among the Dark Triad.