Friends-with-benefits relationships combine elements of friendship with sexual intimacy. Using hierarchical regression, the authors examined perceived deception in 310 relationships. In comparison with men, women reported greater deception by their friends-with-benefits partner. Perceived deception was inversely related to awareness of relational risk factors and directly related to anxious attachment, more sexual interactions as compared with friendship interactions in the relationship, and more favorable attitudes toward ambiguous commitment. Awareness of relational risk factors moderated the association between anxious attachment and perceptions of being deceived as awareness of relational risk factors was only negatively associated with perceived deception for those with lower levels of anxious attachment. Last, gender moderated the association between perceptions of being deceived and anxious attachment in that more anxious attachment was related to perceived deception for women, but not men. In particular, anxious attachment did not predict perceptions of deception for men, but greater degrees of anxious attachment for women increased perceptions of deception. Recommendations for assisting young adults to navigate this relational style are offered.