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The present study investigated the relationship between Machiavellianism, envy, competition, and schadenfreude in women’s same-sex friendships. Women (N = 133) completed an online questionnaire measuring Machiavellianism, envy, competition, and three author-generated vignettes measuring expressed schadenfreude in relation to a same-sex friend. Women with higher levels of Machiavellianism expressed greater feelings of pleasure in response to their same-sex friend’s misfortunes in a romantic relationship and their physical appearance but not in relation to academic abilities. Envy predicted feelings of schadenfreude in academic and romantic relationships while competition predicted feelings of schadenfreude in all three scenarios. Future research should explore how characteristics of the target and different forms of envy may influence responses to a friend’s misfortune in individuals with higher levels of Machiavellianism.