In this study, the relationship between individuals’ insecure attachment styles and eight comic styles was explored. A sample of 636 Italian adults (206 males, 428 females, 2 non-binary), aged 18 to 81 years (M = 41.44; DS = 13.44) completed an online survey to investigate the relationship between insecure attachment styles, namely anxious and avoidant, and the eight comic styles, clustered into lighter style (fun, benevolent humor, wit, nonsense) and darker style (irony, satire, sarcasm, cynicism). The findings of this research indicated the lighter and darker styles were differently related to the anxious and avoidant styles. The anxious attachment was negatively related to both benevolent humor and wit and positively with irony. The avoidant style was positively associated with nonsense and sarcasm, while no other relationship emerged. This research indicated that attachment orientations are associated with individual differences in the detailed differentiation of humor-related styles.