Although theory and research evidence indicate that less securely attached persons are more likely than their secure peers to experience emotion regulation difficulties, this is not necessarily a pre-ordained outcome. Emotion regulation difficulties may be more proximally predicted by individuals’ maladaptive psychological defenses such as humor styles. This study explored the interrelationships between adult attachment orientations (attachment anxiety and avoidance) and perceived bonds with parents (perceived levels of parental care and control), emotion regulation (cognitive reappraisal and expressive suppression), and maladaptive humor styles (aggressive and self-defeating humor). Attachment anxiety, avoidance, and maternal care and overprotection were associated in expected directions with aggressive and self-defeating humor, but paternal care and overprotection were not. Additionally, aggressive and self-defeating humor were positively associated with expressive suppression and negatively associated with cognitive reappraisal. Self-defeating humor partially mediated the relationship between a number of attachment predictors (attachment anxiety, avoidance, maternal care, and maternal control) and expressive suppression. For example, attachment anxiety predicted higher use of self-defeating humor, which in turn predicted higher levels of expressive suppression. Finally, aggressive humor partially mediated the relationship between avoidance and cognitive reappraisal. Avoidance predicted higher use of aggressive humor, which in turn predicted lower levels of reappraisal. Implications for future research and clinical practice are discussed.